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Worst Red Sox Transaction Nomination Thread -- Round 1: Free Agents


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#1 John Marzano Olympic Hero


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Posted 17 March 2011 - 06:11 AM

Over the last week or so, there have been some people who have been pretty down on Daisuke Matsuzaka (before his start against Detroit). Among the things that were said and written was that he was "the biggest waste of money ever" and one of "the worst Boston signings ever". Obviously that's hyperbole and plain wrong.

Which got me thinking, what is the worst transaction the Red Sox made in the free agency era (1975 on)? I wanted to break it down three ways:

-- Multi-year free agent signing (one and outs don't really hurt a team)
-- Trades
-- Drafted players

In this thread, post the worst free agent signings that you can think of and the most popular five will be put into a poll three weeks from now (after we get the top five worst trades and worst drafts). Please bold the name of the free agent. Also use this thread to make your case, argue against other's case and defend your picks. It'll be a real hoot.

This thread will close next Wednesday at 5:00 pm EST.

I'll start it off, signing Matt Young was the worst free agent signing the Boston Red Sox ever made.

#2 EddieYost


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Posted 17 March 2011 - 06:27 AM

Over the last week or so, there have been some people who have been pretty down on Daisuke Matsuzaka (before his start against Detroit). Among the things that were said and written was that he was "the biggest waste of money ever" and one of "the worst Boston signings ever". Obviously that's hyperbole and plain wrong.

Which got me thinking, what is the worst transaction the Red Sox made in the free agency era (1975 on)? I wanted to break it down three ways:

-- Multi-year free agent signing (one and outs don't really hurt a team)
-- Trades
-- Drafted players

In this thread, post the worst free agent signings that you can think of and the most popular five will be put into a poll three weeks from now (after we get the top five worst trades and worst drafts). Please bold the name of the free agent. Also use this thread to make your case, argue against other's case and defend your picks. It'll be a real hoot.

This thread will close next Wednesday at 5:00 pm EST.

I'll start it off, signing Matt Young was the worst free agent signing the Boston Red Sox ever made.


Steve Avery, Jack Clark, Andre Dawson and David Wells all seem pretty bad to me. Only being 2 year deals makes them slightly easier to forget though.

EDIT - I will nominate Andre Dawson. Over 9 million for 2 years of a crappy DH was a lot of dough back then.

Edited by EddieYost, 17 March 2011 - 06:52 AM.


#3 TheShynessClinic


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Posted 17 March 2011 - 06:38 AM

I'll be the first, but I probably won't be the last to nominate Julio Lugo and his 4/36 contract.

In his three years with the Red Sox he put up an OPS+ of 71 in 1060PA with erratic defense before being traded to St. Louis for Chris Duncan and some sawdust.

Edit: Forgot to bold.

Edited by TheShynessClinic, 17 March 2011 - 06:40 AM.


#4 smastroyin


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Posted 17 March 2011 - 07:24 AM

Someone already took mine in Dawson. Dawson himself wasn't so bad (certainly others have performed worse) but it was more what he represented. How much was Gorman's fault we'll never know but the Sox spent those early 90's trying to spend some money and win before JAW died, but none of the marquee guys seemed to want to come here.

I'm going to go with Tony Pena, who I actually like well enough as a guy, but was a horrible horrible hitter for the Red Sox. He was a good catcher and good team guy and maybe I wouldn't have minded so much if the rest of the offense was actually useful, but there are only so many sinkholes a lineup can take and those early 90's teams were full of them.

Bolding per JMOH. Dawson is my true choice and who I would vote for.

#5 The Four Peters


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Posted 17 March 2011 - 07:36 AM

I'm going to go with Tony Pena, who I actually like well enough as a guy, but was a horrible horrible hitter for the Red Sox. He was a good catcher and good team guy and maybe I wouldn't have minded so much if the rest of the offense was actually useful, but there are only so many sinkholes a lineup can take and those early 90's teams were full of them.

Man, this is nostalgia kicking in but I absolutely loved Tony Pena solely due to the 1990 team. I used to watch games while sitting with one leg pointed out just because I wanted to be him and I thought that was the coolest thing that my 8 year old self had ever seen. But then I go and look at his actual numbers during those years and he was just impossibly inept with the bat.

For nominations, I'll throw Steve Avery out there. It was only 2 years that he was here, but he made good money too be horrifically bad on the mound. Even worse, he was coming in to nominally replace Clemens, which was just a catastrophic failure.

#6 Buzzkill Pauley


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Posted 17 March 2011 - 07:38 AM

I go with Tony Pena, 4 yrs/$8.6MM.

The numbers seem quaint now, but his deal made him the third-highest paid member of the team in 1990, after only Clemens and Boggs. So he went out the next four years and put up 1849 plate appearances at a 64 OPS+ clip. Sure he won a gold glove, and he may have been a good defensive catcher, but does that really excuse his offense?

Average line, 1990-93:
136 G, 462 PA, 98 H, 18 2B, 1 3B, 4 HR, .234/.290/.313.


Possibly the best thing about the current front office -- if a move doesn't work out, they move on quickly. It's rare to see the team keep throwing out any player's corpse game after game these days.

#7 jose melendez


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Posted 17 March 2011 - 07:42 AM

That Matt Young off season was nightmarish. As I recall, it included Danny Darwin and Jack Clark too, neither of which turned out to be too great. Of course, the thing that kills me is that Darwin pitched pretty well again after he left Boston. That said, Young really does take the cake. We got a couple seasons of sub 4 ERA from Darwin, and Clark at least gave us an OPS above .800 his first year.

I'd also add, that it's hard to leave Edgar Renteria off the list

#8 John Marzano Olympic Hero


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Posted 17 March 2011 - 08:04 AM

Someone already took mine in Dawson.


Remember, you can choose someone that has already been picked. And remember, this is a popularity contest, so it's ok.

And I'm with Peters, when I was younger I was a huge Tony Pena guy. I liked his snap throws to first, his catching stance, his throwing runners out at second from his knees. He was as flashy a catcher as I've ever seen and I loved him. He was the anti-Rich Gedman (who I grew to despise after his 87 free agency debacle -- I wasn't old enough to understand collusion, so I assumed it was his fault and that he was being greedy).

The most ironic thing about Pena was that his biggest homer in a Red Sox game didn't come when he was with Boston. It was when he hit that bomb off Rick Aguliera in Game 1 of the 1995 ALDS. God, that hurt.

#9 Lose Remerswaal


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Posted 17 March 2011 - 08:06 AM

Jack Clark immediately came to mind, but I was catching up on Posnanski yesterday and he had an article that discussed Jose Offerman, so I'll nominate him for his 3+ years of suckitude with the Sox (although he did hit more 3B than HR, and NO ONE was better than him at going back for a popup). He still hasn't replaced Mo Vaughn's bat.

#10 doctormoist


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Posted 17 March 2011 - 08:06 AM

Tony Clark
Cliff Floyd
Ramiro Mendoza

#11 Smiling Joe Hesketh


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Posted 17 March 2011 - 08:10 AM

Remember, you can choose someone that has already been picked. And remember, this is a popularity contest, so it's ok.

And I'm with Peters, when I was younger I was a huge Tony Pena guy. I liked his snap throws to first, his catching stance, his throwing runners out at second from his knees. He was as flashy a catcher as I've ever seen and I loved him. He was the anti-Rich Gedman (who I grew to despise after his 87 free agency debacle -- I wasn't old enough to understand collusion, so I assumed it was his fault and that he was being greedy).

The most ironic thing about Pena was that his biggest homer in a Red Sox game didn't come when he was with Boston. It was when he hit that bomb off Rick Aguliera in Game 1 of the 1995 ALDS. God, that hurt.

The home run he hit was off Zane Smith. Aguliera gave up the tying HR to Albert Belle a couple of innings before.

Turn in your fan card, thanks.

This one isn't even close: Matt Young. 3-11, 4.91 ERA, 1.607 WHIP in two years in Boston. 3 years/6.5 million for that, which was huge money at the time. I remain absolutely convinced that the only reason Gorman signed Young was due to this game and this game which both took place the previous year when Young was with Seattle. And that's why Lou Gorman was a horrible GM.

Some of the other guys mentioned in this thread don't remotely come close to Young's suckiness: Offerman at least had one very good season in Boston (1999), as did Clark in 1991.

#12 joe dokes

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Posted 17 March 2011 - 08:10 AM

Skip Lockwood.



edit to embolden

Edited by joe dokes, 18 March 2011 - 12:54 PM.


#13 jose melendez


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Posted 17 March 2011 - 08:12 AM

Tony Clark
Cliff Floyd
Ramiro Mendoza



To my mind you have to have two things going to win this category, a bad contract and bad performance. A guy who we payed bug money too for one year who went on to suck is simply not as bad as, for example, Julio Lugo.

And as for Clark, take a look at his 91 numbers They're not horrible.

28 HR, 87 RBI, OPS+ pf 127. That better than two of the four years of JD Drew.

#14 smastroyin


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Posted 17 March 2011 - 08:13 AM

Tony Clark
Cliff Floyd
Ramiro Mendoza


Floyd was a trade.

edit: Jose, you have the wrong Clark. Tony's the one who was more concerned with the MLBPA than with the Boston Red Sox and who totally sucked ass in a year where his bat would have made a big difference.

I realize people liked Pena, but to me that whole era (Pena, Dawson as FA signings, trades for Brunansky, Hatcher) represented some kind of weird vortex where Gorman decided that replacing the Sox old players with other people's old players was a viable strategy, instead of trying to get younger or better. Although, again, it's hard to slice the blame pie for why they couldn't close on any of the bigger FA's. Various reports were that they were in on Henderson, Bonds, and McGwire among others.

#15 jose melendez


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Posted 17 March 2011 - 08:14 AM

The home run he hit was off Zane Smith. Aguliera gave up the tying HR to Albert Belle a couple of innings before.

Turn in your fan card, thanks.

This one isn't even close: Matt Young. 3-11, 4.91 ERA, 1.607 WHIP in two years in Boston. 3 years/6.5 million for that, which was huge money at the time. I remain absolutely convinced that the only reason Gorman signed Young was due to this game and this game which both took place the previous year when Young was with Seattle. And that's why Lou Gorman was a horrible GM.

Some of the other guys mentioned in this thread don't remotely come close to Young's suckiness: Offerman at least had one very good season in Boston (1999), as did Clark in 1991.



I think that's pretty much right. Throw in the fact that he couldn't throw to first, and I can't really imagine a worse signing.

#16 RingoOSU


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Posted 17 March 2011 - 08:17 AM

Jack Clark immediately came to mind, but I was catching up on Posnanski yesterday and he had an article that discussed Jose Offerman, so I'll nominate him for his 3+ years of suckitude with the Sox (although he did hit more 3B than HR, and NO ONE was better than him at going back for a popup). He still hasn't replaced Mo Vaughn's bat.

I second Jose Offerman, his 4/26 in 1998 was Lugo before there was Lugo. Also, he later got banned for life from the Dominican League, so more proof he's just a bad idea in general.
I can't believe he got even a nomination for the Royals HOF.

#17 John Marzano Olympic Hero


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Posted 17 March 2011 - 08:30 AM

The home run he hit was off Zane Smith. Aguliera gave up the tying HR to Albert Belle a couple of innings before.

Turn in your fan card, thanks.


Of course.

I was a senior in college at the time. I'm lucky I could remember my name.

#18 JMDurron

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Posted 17 March 2011 - 08:34 AM

Replacing Fergie Jenkins (trade) with Mike Torrez (FA) might be one of the worst combined moves, but for a pure FA signing, I'm hopping onto the Matt Young train as well.

#19 Smiling Joe Hesketh


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Posted 17 March 2011 - 08:38 AM

Replacing Fergie Jenkins (trade) with Mike Torrez (FA) might be one of the worst combined moves, but for a pure FA signing, I'm hopping onto the Matt Young train as well.

Crazy as it sounds, Torrez really wasn't terrible for the Sox. 60-51, 4.51 ERA, 95 ERA+ over 5 years in Boston. He wasn't great and probably wasn't worth anywhere near his contract, but he had some pretty decent years here. He provided some value.

I agree in terms of trading away Jenkins. I understand he was a Buffalo Head and Zimmer hated those guys, but the Sox essentially threw away a fantastic pitcher.

#20 SeanBerry


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Posted 17 March 2011 - 08:40 AM

The Lugo deal was amazingly awful but he did contribute in a World Series so I can't count him as the worst ever. The Offerman contract was total shit too but he did have a nice year in 1999 and was great in the playoffs to boot.

My pick is for Matt Young.

#21 EddieYost


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Posted 17 March 2011 - 08:41 AM

I think that's pretty much right. Throw in the fact that he couldn't throw to first, and I can't really imagine a worse signing.


Right, I nominated Hawk Dawson but would vote for Matt Young. I think that offseason (Darwin/Clark/Matt Young) has to be one of the worst ever, right alongside losing Fisk, Lynn and Burleson in the same offseason.

#22 DanoooME


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Posted 17 March 2011 - 08:44 AM

Ill go with Tony Pena too. He was great in Pittsburgh, but boy did he suck here. OPS+ of 84, 66, 62 and 32.

I agree with Avery and Young as well.

#23 Hyde Park Factor


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Posted 17 March 2011 - 08:48 AM

Jack Clark immediately came to mind, but I was catching up on Posnanski yesterday and he had an article that discussed Jose Offerman, so I'll nominate him for his 3+ years of suckitude with the Sox (although he did hit more 3B than HR, and NO ONE was better than him at going back for a popup). He still hasn't replaced Mo Vaughn's bat.


IIRC, he was supposed to replace Mo Vaughn's on base capabilities. Whatever that means.

Jumping on the Matt Young bandwagon here. Of course some may remember him as Door Matt, others as Sigh Young. I remember him as the guy who pitched a no-hitter and still lost the game (he allowed 2 runs on 7 walks with an error by Luis Rivers thrown in for good measure).

Edited by Hyde Park Factor, 17 March 2011 - 08:53 AM.


#24 Larry Gardner

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Posted 17 March 2011 - 08:51 AM

Tony Clark
Cliff Floyd
Ramiro Mendoza


I remember Tony Clark hitting a 3-run HR on opening day and getting really excited. What a waste of a season. Only favor he ever did for the Sox was bouncing the ball into the RF stands in Game 4 of the ALCS in '04.

I had to look up both Ivan Calderon and Smooth Hittin' Mark Whiten, and they were trades, but threads like this one make me remember their crap performances.

#25 smastroyin


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Posted 17 March 2011 - 09:02 AM

Only favor he ever did for the Sox was bouncing the ball into the RF stands in Game 4 of the ALCS in '04.


Game 5


Foulke also fanned him to end Game 6.

#26 ScubaSteveAvery


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Posted 17 March 2011 - 09:06 AM

I'm going to go with Steve Avery. 2 years at $8 million at the time was still a decent chunk of money. He hadn't pitched a good season since 1993, and was clearly a different, entirely less effective pitcher by the time Boston signed him. He couldn't even muster 100 innings in 1997. He walked more batters than he struck out during his 2 years here. He wasn't signed to be the #5 mop up guy. He was the clear #2, slotted behind Pedro and brought in to replace Clemens. The guy flat out sucked and cost the team some decent coin doing so.

#27 EddieYost


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Posted 17 March 2011 - 09:14 AM

I had to look up both Ivan Calderon and Smooth Hittin' Mark Whiten


I completely do not recall Ivan Calderon being on the Red Sox.

#28 The Four Peters


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Posted 17 March 2011 - 09:14 AM

I'm going to go with Steve Avery. 2 years at $8 million at the time was still a decent chunk of money. He hadn't pitched a good season since 1993, and was clearly a different, entirely less effective pitcher by the time Boston signed him. He couldn't even muster 100 innings in 1997. He walked more batters than he struck out during his 2 years here. He wasn't signed to be the #5 mop up guy. He was the clear #2, slotted behind Pedro and brought in to replace Clemens. The guy flat out sucked and cost the team some decent coin doing so.

He was actually signed the year before they acquired Pedro as the #1 for 1998 season. The rotation in 1997 (by IP):
Tim Wakefield
Tom Gordon
Aaron Sele
Jeff Suppan
Steve Avery

I have no idea how people can include Offerman as a top 3-5 worst free agent signing by any stretch. He certainly didn't fulfill the contract or expectations, but he was damn good in 1999 and marginally decent in 2000. The 1999 year alone should probably preclude him from the discussion.

We're talking some catastrophic busts here (Young, Avery, Pena, etc), not overall disappointments.

#29 Smiling Joe Hesketh


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Posted 17 March 2011 - 09:15 AM

I'm going to go with Steve Avery. 2 years at $8 million at the time was still a decent chunk of money. He hadn't pitched a good season since 1993, and was clearly a different, entirely less effective pitcher by the time Boston signed him. He couldn't even muster 100 innings in 1997. He walked more batters than he struck out during his 2 years here. He wasn't signed to be the #5 mop up guy. He was the clear #2, slotted behind Pedro and brought in to replace Clemens. The guy flat out sucked and cost the team some decent coin doing so.

Avery's first year in Boston was the year before Pedro got here, so he was never initially meant to be slotted in as the #2 behind Pedro.

His arm was pretty much toast by the time he got to Boston. The Sox and Duquette were betting that he'd return to his early Braves form. They lost that bet.

EDIT: Damn you TFP.

#30 Doug Beerabelli


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Posted 17 March 2011 - 09:23 AM

Can Bob Stanley be included? IIRC, when they signed Steamer but failed on Pudge, that whole debacle, I think Stanley was technically a FA, or about to be one.

If not, ignore the above, and blame Lugo

#31 smastroyin


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Posted 17 March 2011 - 09:25 AM

To be fair to Duquette, there was no way Avery should have been around for a second season. Of course, Duquette also hired Jimy Williams so he has noone else to blame.

I don't think he was brought in as a clear #2 either. I would think of him more along the lines of a Wade Miller or John Smoltz. The problem in 97 was that there were a lot of those guys and they all failed miserably.

#32 Red(s)HawksFan


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Posted 17 March 2011 - 09:33 AM

To be fair to Duquette, there was no way Avery should have been around for a second season. Of course, Duquette also hired Jimy Williams so he has noone else to blame.

I don't think he was brought in as a clear #2 either. I would think of him more along the lines of a Wade Miller or John Smoltz. The problem in 97 was that there were a lot of those guys and they all failed miserably.

That may have been true, but 2/$8M in 1997 was still a big investment on a reclamation project. He was the highest paid pitcher on the team in 1997 (2nd highest overall behind Vaughn). And the second highest paid pitcher (after Pedro) in 1998. I don't know that he quite falls into the same type of category as Miller or Smoltz. The guy who fits that category for Duquette in that era is probably Wakefield or Erik Hansen rather than Avery.

#33 Trautwein's Degree


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Posted 17 March 2011 - 09:39 AM

I agree with the names being thrown around in this thread. Namely Matt Young, Steve Avery and Julio Lugo.

But I'll throw this out there, during the 1994 strike the Red Sox agreed to a deals with Sammy Sosa, Kevin Appier, and John Wetteland. MLB canned the deal. The strike resolved and when it did Sammy decided to remain a Cub. As much as I don't like what Sosa, it would have been electric having him in a Sox uniform from 1995 to 2004. Wetteland of course would go on to anchor the Yankees bullpen during their 1996 title run.

"Signing" Sammy, Wetteland, and Appier at the wrong time or failing to keep those deals in place at the right time was worse than Matt Young, Julio Lugo, and Steve Avery's combined awful. Having Appier, Wetteland, and Sosa may have resulted in a title sooner than 2004.

Duquette swooped in that January and lined up deals with three of the marquee players suddenly made available. He signed right-handed starter Kevin Appier to a four-year, $17 million deal and closer John Wetteland to a three-year deal worth $16 million, while also reaching an agreement with slugger Sammy Sosa on a three-year contract that would have paid out $16 million.

The players union eventually got a court injunction against the changes, restoring the old system and nullifying the deals. Duquette spent the rest of the his eight years at the Red Sox helm chasing after deals to bring those three players to Boston, but none would ever don Sox jersey. Link.


Edited by Trautwein's Degree, 17 March 2011 - 10:00 AM.


#34 Alternate34

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Posted 17 March 2011 - 09:47 AM

There are a lot of bad transactions. How do you rank the worst of the worst? I think these are good criteria.

(1) The player did very poorly in their time here. Bad performance is generally more painful than merely being injured, though sometimes it can be difficult. Some guys do so poorly that they get sat for phantom injuries. Usually, it's not too difficult to distinguish and injury from benching due to poor performance.

(2) The deal looks bad in both foresight and hindsight. This is a little more controversial but I think it is something to consider. Really bad signings happen to good front offices as our current front office shows. However, to me, it is worse if you know the signing will be a failure ahead of time.

(3) More money and years for a bad signing makes it worse. Pretty simple. Adjust for the time.

A look at a few of these signings as I think the very worst signings have been covered.

Matt Young

(1) Never pitched a full season in Boston but was bad when he did pitch. Started 16 games in 1991. 88.2 total innings, 5.18 ERA, walked over 5 guys per 9, his ERA+ was 84. 1992, he was coming out of the bullpen a lot, only 8 games started but 28 appearances. 70.2 IP with a 4.58 ERA, a 93 ERA+.

(2) In foresight, this deal was pretty bad, though he had some good season sprinkled in with bad ones. His 1983 debut at age 24 was good, though he was hit lucky. His 1990 season was his only full season starting where he did well. Not coincidentally, that was the season directly previous to his Red Sox debut.

(3) As noted, his contract was pretty big for the time. 3 years at $6.5M total.

Julio Lugo

(1) Well known. B-Ref WAR has his most positive contribution in a season at .4 WAR. I note his best single season because his other seasons when added to that take him to a negative WAR. He was atrocious both offensively and defensively. Was he injured? Were we lucky when he was injured?

(2) Lugo had some good seasons in Tampa Bay from 2003-2005 and was doing OK in Tampa Bay in 2006. When he was traded to the Dodgers, he collapsed. The Red Sox snatched him up hoping for Tampa Bay Lugo who would put up season of 4 WAR (B-Ref). That WAR was often from decent offensive performance and OK defensive performance. He was 31 in his Red Sox debut, which should have been some warning.

(3) He was paid about $9M a season, including a season for the Orioles in 2010.

Tony Pena

(1) He was abysmal offensively for most of his time here, though his debut season was OK. .263/.322/.342 was mediocre for a 1.1 oWAR (B-Ref). He was fun to watch defensively. Unlike Young and Lugo, his "intangibles" are well documented. I haven't seen anything bad written about Pena. He was 21st in the MVP voting in 1990.

(2) He was three years away from his last OPS+ above 100. That understates his value a tad as he was a catcher. His oWAR for his 3 seasons in St. Louis just prior to coming to Boston were -0.6, 1.8, and 0.3. He was 33 when he came to the Red Sox, which is pretty ancient for a catcher, especially a starter.

(3) He made about $2M a year for 4 years. As noted in the Matt Young comment, that was pretty big money in the early 90s.

Jose Offerman

(1) His first season with the Red Sox, 1999, he was a solid offensive presence 26 oRAR with a nifty .391 OBP. His offense dipped for his remaining 3 years. His defense was always painful and awkward to watch. And he started playing some 1B. Where his defense was still bad.

(2) He had just posted a 119 OPS+ for KC the previous year. 3 of the 4 years he came to Boston, he had posted an OPS+ above 100. His defense was always bad during that time.

(3) He made about $6M a year for 4 years in Boston.

Andre Dawson

(1) A DH who posted a negative WAR both years in Boston. He had a .313 OBP his first year. It dropped to a .271 OBP his second year.

(2) Dawson was 38 his debut season and well known for his bad knees. He had just posted a 1.9 oWAR in Chicago, the third straight year of decline for the Hawk.

(3) He was signed for 2 years totalling $9.3M in Boston.

Edgar Renteria

(1) His one year for Boston at SS he made approximately 8000 errors. Offensively, he was meh. He has a 2.4 oWAR. That actually seems weird for a .335 OBP and .385 SLG. Bad year for SS in 2006.

(2) He had just had a down year in St. Louis at 1.8 oWAR. However, his 2 years previous to that, he posted a 6.2 amd 3.7 oWAR. His defense was never as bad as it was in Boston, before and after. He was 28 his debut season in Boston.

(3) He was paid $8M for his season in Boston. He was paid $11M more for his work in Atlanta.

Tony Clark

(1) .207/.266/.291 for a 1B in 2002.

(2) He had just had a 2.2 oWAR season for Detroit. He was 30 when he came to Boston. His only season substantially better than his 2.2 oWAR season was 1997 where he put up a 3.9 oWAR.

(3) He was paid $5M for what he did to us.

Danny Darwin

(1) 4 seasons for the Sox. Injured or ineffective frequently. Jumped from rotation to bullpen. Had a nice 1993 where he started 34 games, pitched 229.1 innings with a 3.26 ERA.

(2) In Houston, he had jumped between the rotation and the bullpen as well. He had good ERAs but that was pretty common for pitchers in the Astrodome. Still, he averaged about 30 RAR per season in his 4 years for Houston and was coming off a 50 RAR season. He was 35 in his debut for Boston.

(3) Paid around $3M/year for 4 years.

Steve Avery

(1) 2 seasons. 6.42 ERA for 96.2 wonderful innings his first. 5.02 ERA for 123.2 stellar innings his second.

(2) Had once been a phenom in Atlanta 4 years before the Red Sox signed him. His arm blew up and he was declining steadily since then. Obviously a gamble by the Red Sox hoping for a return to form.

(3) 2 years at $4.85M and $3.9M. To be fair, Jimy got him that second year. Also to be fair, DD hired Jimy.

I didn't include Jack Clark. He was decent his first year on the Sox. He was certainly better than Dawson.

I'm torn. So many good candidates. I would nominate Andre Dawson with a gun to my head. He was a DH who couldn't hit. He was really old. His knees were becoming legend. $4M a season was a hefty contract. It was only 2 years but it was a lot of money for 2 years. Andre was a classy guy, but he was a terrible player by then.

EDIT - Dawson did not make $9.3M a year. Stupid typo on my part. Still would pick him. $4M was a lot back then as noted in both the Young and Pena comment.

Edited by Alternate34, 17 March 2011 - 10:08 AM.


#35 Eric Van


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Posted 17 March 2011 - 09:48 AM

Over the last week or so, there have been some people who have been pretty down on Daisuke Matsuzaka (before his start against Detroit). Among the things that were said and written was that he was "the biggest waste of money ever" and one of "the worst Boston signings ever". Obviously that's hyperbole and plain wrong.

Which got me thinking, what is the worst transaction the Red Sox made in the free agency era (1975 on)? I wanted to break it down three ways:

-- Multi-year free agent signing (one and outs don't really hurt a team)
-- Trades
-- Drafted players

Might it make sense to vote for the worst trade other than Bagwell for Andersen? Otherwise, I think we're going to go to a lot of effort to see whether 90%, 95%, or 98% of SoSH agrees on that. It's a serious contender for worst trade of all time, after all.

(And not just because what eventually happened; the Sox could have gotten Andersen for Scott Cooper, or for Kevin Morton, Scott Taylor, or Dave Owen, according to Gammons' reports at the time. And it's not like Bagwell was a surprise; the Sox were completely unaware of the park factor at Beehive and hence unaware of Bagwell's off-the-chart MLE's -- something Bill James wrote about the winter after the trade and something his followers, like me, knew about when the trade was made [or more accurately, when the Sporting News Guide arrived with its listing of Bagwell's BB and OBP numbers].)

In general, I think there are three types of transactions that turn out to be bad:

-- Calculated risks. E.g., Matt Clement. There was no way of knowing he'd get hurt and no evidence they miscalculated the risk. I'll always give a F.O. a pass on these.
-- Miscalculated risks. E.g., Julio Lugo. They knew there was a risk regarding his makeup (in this case, both his reaction to certain types of pressure and his dedication to coming back from injury or illness), and they misjudged his makeup and hence the risk involved in signing him.
-- Misjudgments of talent. As above.

I do not think Theo has made the third type of mistake. He's made the second type a few times (also Gagne, reacquiring Mirabelli).

Lugo certainly deserves a nomination but there's no way he deserves to win. He was 7/8 worthless, but he did give us a half-year where he played very well defensively, was above average for the position offensively (and good in the clutch to boot), and in short pretty much demonstrated what they saw in him talent-wise. How did the team do during that half-year? Oh, yeah. As his champion, it still kills me that the guy apparently took the next winter off (rather than working to recover the strength he'd lost when he was ill the previous winter).

#36 ScubaSteveAvery


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Posted 17 March 2011 - 09:48 AM

Avery's first year in Boston was the year before Pedro got here, so he was never initially meant to be slotted in as the #2 behind Pedro.

His arm was pretty much toast by the time he got to Boston. The Sox and Duquette were betting that he'd return to his early Braves form. They lost that bet.

EDIT: Damn you TFP.


My bad about the dates there. Still though, at 2 years, $8 million, he was meant as a top 3 person in the rotation, and given the money at the time, top 2. As RedHawksFan posted, he was the highest paid pitcher on the team in 1997, and second highest paid pitcher in 1998. I'm not sure what the "bet" was in signing him. It was clear that he was not the same pitcher as his early Braves year. I mean, there was no indication that he was the same pitcher. Ever since his arm injury, he was in a steep decline as a player. To think he could return to his previous form was pure delusion, which is why the signing is so bad. Duquette threw big money at a player that had zero chance of living up to expectations or the contract. It would be like Theo today handing Dontrelle Willis a 2 year, $20-25 million dollar contract, and slotting him in behind Lester or Beckett.

Edited by ScubaSteveAvery, 17 March 2011 - 09:50 AM.


#37 SeanBerry


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Posted 17 March 2011 - 09:53 AM

My favorite Steve Avery stat is that he went 2-0 for the 2003 Tigers that went 43-119.

#38 snowmanny

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Posted 17 March 2011 - 09:53 AM

Does Mike Lowellcount? He was a free agent when they re-signed him in 2007-8, of course, and I think that any reasonable analysis told us that the Red Sox had stolen surprising value from him in '06 and especially '07 and it was time to take Philadelphia's draft pick and wish him well. It really seemed as if this was a case where emotion overwhelmed logic with predictably lousy results.

Edit: Bolding

Edited by snowmanny, 17 March 2011 - 09:54 AM.


#39 John Marzano Olympic Hero


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Posted 17 March 2011 - 09:54 AM

Might it make sense to vote for the worst trade other than Bagwell for Andersen? Otherwise, I think we're going to go to a lot of effort to see whether 90%, 95%, or 98% of SoSH agrees on that. It's a serious contender for worst trade of all time, after all.


This makes sense. And you're right, this is the all-time crappiest move of the last 25-50 years. Next week, I'll put this caveat in the Worst Trades Thread.

Thanks.

#40 smastroyin


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Posted 17 March 2011 - 10:03 AM

My bad about the dates there. Still though, at 2 years, $8 million, he was meant as a top 3 person in the rotation, and given the money at the time, top 2. As RedHawksFan posted, he was the highest paid pitcher on the team in 1997, and second highest paid pitcher in 1998. I'm not sure what the "bet" was in signing him. It was clear that he was not the same pitcher as his early Braves year. I mean, there was no indication that he was the same pitcher. Ever since his arm injury, he was in a steep decline as a player. To think he could return to his previous form was pure delusion, which is why the signing is so bad. Duquette threw big money at a player that had zero chance of living up to expectations or the contract. It would be like Theo today handing Dontrelle Willis a 2 year, $20-25 million dollar contract, and slotting him in behind Lester or Beckett.



You guys are really forgetting what salary escalation looked like in the late 90's. It was a bad signing but the only way to not be stuck with major years was to get him to agree to an incentive laden deal. Jimy fucked that up by letting him hit the incentives even though he sucked. But Duquette did hire Jimy. Also, I'm not going to go through the entire off-season again, but there was not a lot available to the Sox once Clemens opted to go to Toronto. also, due to salary escalation of the late 90's I think it is pretty unfair to compare a salary from a contract signed in 96/97 to those signed in the previous couple of years.

One reason I really can't fault the Avery thing is that in my mind Duquette already had his eye on the prize, and that prize was Pedro. Avery was a stop-gap with some upside. We would hardly remember him if Sele or Suppan had lived up to their pre-injury promise. A bad signing within a plan is better to me than things like Dawson where the plan sucked too. I understand that everyone has their own interpretation of how to vote, though.

#41 The Allented Mr Ripley


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Posted 17 March 2011 - 10:07 AM

I agree with the names being thrown around in this thread. Namely Matt Young, Steve Avery and Julio Lugo.

But I'll throw this out there, during the 1994 strike the Red Sox agreed to a deals with Sammy Sosa, Kevin Appier, and John Wetteland. MLB canned the deal. The strike resolved and when it did Sammy decided to remain a Cub. As much as I don't like what Sosa, it would have been electric having him in a Sox uniform from 1995 to 2004. Wetteland of course would go on to anchor the Yankees bullpen during their 1996 title run.

"Signing" Sammy, Wetteland, and Appier at the wrong time or failing to keep those deals in place at the right time was worse than Matt Young, Julio Lugo, and Steve Avery's combined awful. Having Appier, Wetteland, and Sosa may have resulted in a title sooner than 2004.


Sosa didn't decide to remain a Cub, nor did the Sox fail to keep those deals in place. Those guys were free agents under a new FA system imposed by the owners during the offseason before the new CBA was negotiated and signed. The new system required only 4 (5?) years of service time instead of the usual 6. The new CBA retained the 6-year service rule. Which meant Sosa, Appier and Wetteland were no longer free agents, as they didn't have the required service time.

It wasn't up to the players or the Sox, the contracts they signed were nullified by the new CBA.

Edited by The Allented Mr Ripley, 17 March 2011 - 10:13 AM.


#42 mikeford


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Posted 17 March 2011 - 10:09 AM

In honor of my dad, who friggin hated the guy and his dumb stance behind the plate, I am throwing a vote Tony Pena's way.

#43 Trautwein's Degree


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Posted 17 March 2011 - 10:20 AM

Sosa didn't decide to remain a Cub, nor did the Sox fail to keep those deals in place. Those guys were free agents under a new FA system imposed by the owners during the offseason before the new CBA was negotiated and signed. The new system required only 4 (5?) years of service time instead of the usual 6. The new CBA retained the 6-year service rule. Which meant Sosa, Appier and Wetteland were no longer free agents, as they didn't have the required service time.

It wasn't up to the players or the Sox, the contracts they signed were nullified by the new CBA.


Looking more closely, Wetteland was traded to the Yankees on April 5, 1995 for Fernando Seguignol and cash. He didn't sign with the Yankees as a free agent. He became a free agent in 1996 and hopped the first plane out of NY to Texas.

#44 Joe D Reid

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Posted 17 March 2011 - 10:20 AM

Based on all the antilove for Lugo, I think we need to take a look at Edgar Renteria as well. In his one year with the Sox he put up a line of .276/.335/.385, compared to Lugo's combined .251/.319/.391. Each guy put up a B-WAR of 0.4 (B-R's system really, really hated Renteria's defense). Their per-year salaries were close, too, with Edgar at $8M and Lugo at an average of something like $8.75. So by the numbers, they were remarkably similar over their time here.

I think there are two non-performance issues that come up when you compare them, with each guy faring better on one than the other. As people have noted, Lugo may have sucked, but he was the SS on a World Series-winning team, while Renteria was only here long enough to be on the receiving end of an ass-kicking from Chicago. On the other hand, the Sox were forced to drag around Lugo's contract more or less forever, like Marley's chains, whereas they got out from under Renteria much more quickly.

In any event, I think the two guys are close enough that if we're nominating one, we should nominate both.

#45 Alternate34

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Posted 17 March 2011 - 10:26 AM

Based on all the antilove for Lugo, I think we need to take a look at Edgar Renteria as well. In his one year with the Sox he put up a line of .276/.335/.385, compared to Lugo's combined .251/.319/.391. Each guy put up a B-WAR of 0.4 (B-R's system really, really hated Renteria's defense). Their per-year salaries were close, too, with Edgar at $8M and Lugo at an average of something like $8.75. So by the numbers, they were remarkably similar over their time here.

I think there are two non-performance issues that come up when you compare them, with each guy faring better on one than the other. As people have noted, Lugo may have sucked, but he was the SS on a World Series-winning team, while Renteria was only here long enough to be on the receiving end of an ass-kicking from Chicago. On the other hand, the Sox were forced to drag around Lugo's contract more or less forever, like Marley's chains, whereas they got out from under Renteria much more quickly.

In any event, I think the two guys are close enough that if we're nominating one, we should nominate both.


To me, Lugo is worse because his signing was less justified. Renteria was younger when signed and had had some better seasons than Lugo's best. Renteria's defensive collapse was surprising. He had always been an OK glove at SS, not a disastrously bad defender.

Additionally, as you mentioned, they couldn't get out from under Lugo's contract. They were able to pay a lot less on Renteria's.

#46 Smiling Joe Hesketh


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Posted 17 March 2011 - 10:29 AM

Based on all the antilove for Lugo, I think we need to take a look at Edgar Renteria as well. In his one year with the Sox he put up a line of .276/.335/.385, compared to Lugo's combined .251/.319/.391. Each guy put up a B-WAR of 0.4 (B-R's system really, really hated Renteria's defense). Their per-year salaries were close, too, with Edgar at $8M and Lugo at an average of something like $8.75. So by the numbers, they were remarkably similar over their time here.

I think there are two non-performance issues that come up when you compare them, with each guy faring better on one than the other. As people have noted, Lugo may have sucked, but he was the SS on a World Series-winning team, while Renteria was only here long enough to be on the receiving end of an ass-kicking from Chicago. On the other hand, the Sox were forced to drag around Lugo's contract more or less forever, like Marley's chains, whereas they got out from under Renteria much more quickly.

In any event, I think the two guys are close enough that if we're nominating one, we should nominate both.

They had to pay a substantial part of Renteria's salary when they traded him away, IIRC.

Renteria's issues in Boston were, I believe, caused due to a chronic bad back which made him very, very stiff in the field. Lugo was simply a miss on the evaluation of a player. Renteria had just come off seasons of 113 and 130 OPS+ when he was signed, and upon his return to the NL he promptly put up seasons of 104 and 124 OPS+. Lugo had had exactly one full season of an OPS+ of more than 100 when he was signed: 2005. Lugo had had a good 1/2 year with Tampa in 2006 before being traded to LA and cratering out. If the Sox were thinking that he'd return to that 1/2 year form he had with Tampa, they got is terribly wrong and cost themselves a great deal of money in the process.

Lugo did play well in the World Series. I will always give him that much.

#47 Rudy Pemberton


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Posted 17 March 2011 - 10:41 AM

They had to pay a substantial part of Renteria's salary when they traded him away, IIRC.


Yeah, but they got super-stud and future $100M player Andy Marte :)

#48 Rough Carrigan


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Posted 17 March 2011 - 10:50 AM

Skip Lockwood

Edited by Rough Carrigan, 17 March 2011 - 07:47 PM.


#49 Doug Beerabelli


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Posted 17 March 2011 - 10:50 AM

This thread is actually heartening. All the nominations are for contracts under $40 million and 4 years. For a big market club, I think that's pretty impressive. There have been teams with worse single season FA signings than those mentioned in this thread (I'm thinking the year the Rockies signed Hampton and Neagle as prime example).

Kei Igawa would win this thread.

#50 Red(s)HawksFan


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Posted 17 March 2011 - 10:52 AM

The only thing that the Renteria and Lugo cases have in common is that they signed similar deals to play SS for the Sox. Yes, Renteria's one season in Boston wasn't all that great, especially defensively. But he was rightly far more regarded and deserving of the deal he got than Lugo ever was. Renteria was a year removed from a gold glove season in which he posted a 130 OPS+ when he signed as a 27-year-old. He went on during the life of that contract to post 104 and 124 OPS+ seasons for the Braves.

I think dealing him away when they did was more egregious than signing him in the first place. I thought it was a panic move at the time, and one that eventually necessitated the Lugo signing. I would have liked to see a healthy Renteria for a season before completely giving up on him. I find it kinda funny that the stories about Scutaro this spring have praised him for battling through pain and injury to lead the team in games played last year, and that's a big reason why they're loathe to let Lowrie usurp his starting role. But Renteria had a nearly identical season in 2005 (maybe a few more errors in the field), and promptly got shipped out of town.