Worst Red Sox contracts ever

Beale13

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Well that would be a change from his usual seasons where he goes to shit in August.

Seriously I'm beyond done with this guy. What a senseless waste of money.
Has to be one of the worst Sox contracts ever. There have been bigger wastes of money, but I can't think of one that looked so obviously bad at the moment the deal was executed (and it has been living up to every bad expectation), rather than looking terrible primarily in hindsight. Sandoval might be the only one that comes close.
 

Manuel Aristides

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Has to be one of the worst Sox contracts ever. There have been bigger wastes of money, but I can't think of one that looked so obviously bad at the moment the deal was executed (and it has been living up to every bad expectation), rather than looking terrible primarily in hindsight. Sandoval might be the only one that comes close.
Maybe Carl Crawford. Though it looked less awful at the start.
 

donutogre

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Maybe Carl Crawford. Though it looked less awful at the start.
For me, it's the Pablo Sandoval contract, though Crawford has to be a close second. I feel like with Crawford there was some hope he'd live up to some of the contract, whereas Sandoval made no sense right from the jump.
 

Apisith

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We’re 3 weeks past the date he got injured. Given the 4-6 week timeline, hoping we get an update in a week or so about when he’ll start throwing.
 

Max Power

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Maybe Carl Crawford. Though it looked less awful at the start.
Crawford looked like a good signing, even if he might be a bit overpaid. His last year in Tampa he put up a 135 OPS+ with 47 steals and played in over 150 games. There was no hint of decline or injuries. He should have been good for at least a few years at the time they signed him, but he immediately collapsed. It was very weird.
 

nvalvo

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Maybe Carl Crawford. Though it looked less awful at the start.
The Crawford contract was terrible, but it looked great on paper. We had a need in the outfield, and we signed a dynamic outfielder coming off a 7 WAR season for a division rival to a huge deal. We grumbled about it because he seemed slightly miscast in left field, and because we all didn't like him in Tampa, but I don't think anyone would have predicted that the entire rest of his career would be worth about half that previous season.
 

Red(s)HawksFan

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Crawford looked like a good signing, even if he might be a bit overpaid. His last year in Tampa he put up a 135 OPS+ with 47 steals and played in over 150 games. There was no hint of decline or injuries. He should have been good for at least a few years at the time they signed him, but he immediately collapsed. It was very weird.
To me, Crawford was a bad signing from the jump even if he appeared like he would be a good player for a few years more. Primarily because he didn't really fit the Red Sox roster at the time. He always felt to me like a square peg for a round hole. He was a LHH whose best attribute (speed) was something they already had at the top of the order (Ellsbury) so he was destined to hit in the bottom half of the order (somewhere 6 through 9). He was a defender whose strongest attribute (speed) was wasted playing 81 games a year in LF at Fenway. The Red Sox could have filled his spot with someone that was half the cost (or less) and would have been far better off.
 

PC Drunken Friar

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The Crawford contract was terrible, but it looked great on paper. We had a need in the outfield, and we signed a dynamic outfielder coming off a 7 WAR season for a division rival to a huge deal. We grumbled about it because he seemed slightly miscast in left field, and because we all didn't like him in Tampa, but I don't think anyone would have predicted that the entire rest of his career would be worth about half that previous season.
He also didn't want to be here. I may be misremembering, but wasn't there talk that there was pressure on him to sign the biggest deal "for the good of the players?" Also, he was a Boras client at the time.
 

BaseballJones

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Crawford looked like a guy who was just about to explode. He was on the rise, in his prime, and looked phenomenal. His two years previous to arriving in Boston:

2009: 156 g, .305/.364/.452/.816, 116 ops+, 15 hr, 60 sb, 5.0 bWAR
2010: 154 g, .307/.356/.495/.851, 135 ops+, 19 hr, 47 sb, 7.0 bWAR

And his Fenway numbers were good:

2009: 38 ab, .342/.350/.500/.850
2010: 37 ab, .324/.350/.432/.782

There was literally no reason, baseball-wise, to think that he wouldn't be terrific for Boston for a number of years. Healthy. Fast. Good defender (not great, but good). Great on the base paths. Surprising power. Fit a need. Excellent all-around player. All-star in both 2009 and 2010, and deservedly so, not one of those "how the hell did he make it" kind of selections.
 

nvalvo

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Crawford looked like a guy who was just about to explode. He was on the rise, in his prime, and looked phenomenal. His two years previous to arriving in Boston:

2009: 156 g, .305/.364/.452/.816, 116 ops+, 15 hr, 60 sb, 5.0 bWAR
2010: 154 g, .307/.356/.495/.851, 135 ops+, 19 hr, 47 sb, 7.0 bWAR

And his Fenway numbers were good:

2009: 38 ab, .342/.350/.500/.850
2010: 37 ab, .324/.350/.432/.782

There was literally no reason, baseball-wise, to think that he wouldn't be terrific for Boston for a number of years. Healthy. Fast. Good defender (not great, but good). Great on the base paths. Surprising power. Fit a need. Excellent all-around player. All-star in both 2009 and 2010, and deservedly so, not one of those "how the hell did he make it" kind of selections.
Exactly! It was reasonable to project that he might add 25-30 HR pop to his good OBPs and dozens of stolen bases. It looked like we might get some prime Rickey Henderson-type seasons out of him.
 

LogansDad

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Exactly! It was reasonable to project that he might add 25-30 HR pop to his good OBPs and dozens of stolen bases. It looked like we might get some prime Rickey Henderson-type seasons out of him.
I don't know about prime Rickey, but I LOVED Crawford in Tampa and was absolutely pumped when the Sox got him. I'm also a giant idiot, so, that worked out well.
 

lexrageorge

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Crawford looked like a guy who was just about to explode. He was on the rise, in his prime, and looked phenomenal. His two years previous to arriving in Boston:

2009: 156 g, .305/.364/.452/.816, 116 ops+, 15 hr, 60 sb, 5.0 bWAR
2010: 154 g, .307/.356/.495/.851, 135 ops+, 19 hr, 47 sb, 7.0 bWAR

And his Fenway numbers were good:

2009: 38 ab, .342/.350/.500/.850
2010: 37 ab, .324/.350/.432/.782

There was literally no reason, baseball-wise, to think that he wouldn't be terrific for Boston for a number of years. Healthy. Fast. Good defender (not great, but good). Great on the base paths. Surprising power. Fit a need. Excellent all-around player. All-star in both 2009 and 2010, and deservedly so, not one of those "how the hell did he make it" kind of selections.
Bingo. I do recall at the time of the signing some posters here, and even some media pundits, questioning the overall roster fit given the terms of Crawford's contract. But there was literally nothing to suggest that he was going to fall off a literal cliff at the age of 29 while playing in a park that should have been very friendly to him.
 

Beale13

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His contract, and how it affects the team, are what they are and rehashing whether it was a "good idea" became a waste of time after the 1000th iteration.
At this point and going forward, I'm lumping Sale in with all those other pitchers who don't fully recover from TJS until they've had an offseason that doesn't involve recovering from TJS. The rib thing will heal and let's see where he's at.
I suppose we could end every conversation about John Lackey's contributions in 2013 with "yeah, but he sucked most of the rest of time he was here." But do we have to?

I'm in the camp that thinks one series-changing contribution that leads to a championship is enough to make almost any contract worthwhile. JD Drew, John Lackey, David Price, all earned their contracts as far as I'm concerned. Sale's 2018 contribution came before the extension, but I hold out hope that he contributes to a championship during this contract. It's just disheartening to see so much evidence that the contract is going to play out exactly like it looked like it would when it was executed.
 

OCD SS

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Re: Crawford. At the time I thought the Sox were looking at needing 2 OFers in the near term, so definitely needed at least 1 big acquisition that off season, for me Crawford was the guy to get as an athletic player coming into his prime, as opposed to Werth, who we’d be paying to decline.

It didn’t work out but it didn’t work out, but many of the arguments against his signing still don’t make sense to me (summarized nicely by Red…)
To me, Crawford was a bad signing from the jump even if he appeared like he would be a good player for a few years more. Primarily because he didn't really fit the Red Sox roster at the time. He always felt to me like a square peg for a round hole. He was a LHH whose best attribute (speed) was something they already had at the top of the order (Ellsbury) so he was destined to hit in the bottom half of the order (somewhere 6 through 9). He was a defender whose strongest attribute (speed) was wasted playing 81 games a year in LF at Fenway. The Red Sox could have filled his spot with someone that was half the cost (or less) and would have been far better off.
Good players can play, and a good manager should be able to find a way to assemble the pieces. I just do not get the last part about his speed somehow not playing in Fenway’s LF at all. No one is so fast that they can cover the entirety of LF even with the Monster limiting the back boundaries and being able to cover the space laterally would pay dividends on defense. You can argue that you’d rather have a Manny type masher who’s negative defensively and take the trade off, but that is a fundamentally different argument and one that is refuted by the structure of the 2018 OF with Benni in LF.
 

TFisNEXT

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I'm in the camp that thinks one series-changing contribution that leads to a championship is enough to make almost any contract worthwhile. JD Drew, John Lackey, David Price, all earned their contracts as far as I'm concerned. Sale's 2018 contribution came before the extension, but I hold out hope that he contributes to a championship during this contract. It's just disheartening to see so much evidence that the contract is going to play out exactly like it looked like it would when it was executed.
I agree with this. This is why these types of players are signed. Obviously we’d all love them to live up to their big contracts in terms of WAR (ala Manny or Pedro) but if Chris Sale has his “John Lackey beating Justin Verlander 1-0 in a pivotal road ALCS game” moment, then I’m stamping it as a success. Those types of moments define a post season. Do the Red Sox win the ALCS without that Lackey game? I sure as hell wouldn’t want to find out.
 

Yelling At Clouds

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I guess I generally think contracts are tough to judge until they’re over. I can recall a different pitcher DD once signed to an extension who was kind of meh in the first year and then injured in the second. We all would have been apoplectic! But in the final analysis, Justin Verlander’s extension before the 2013 season wound up working out pretty well.

Do I think it’s likely Sale is a Cy contender again? I do not. But I don’t think “useful, perhaps even good” is out of the question.
 

Sprowl

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Split off from the Chris Sale injury thread.

***
Exactly! It was reasonable to project that he might add 25-30 HR pop to his good OBPs and dozens of stolen bases. It looked like we might get some prime Rickey Henderson-type seasons out of him.
Bingo. I do recall at the time of the signing some posters here, and even some media pundits, questioning the overall roster fit given the terms of Crawford's contract. But there was literally nothing to suggest that he was going to fall off a literal cliff at the age of 29 while playing in a park that should have been very friendly to him.
Carl Crawford's power was always as a dead pull hitter going to the largest right field in baseball. His speed on the basepaths was exaggerated by being able to run on Varitek's noodle arm 19 games a year. His speed in the outfield was devalued by spending all his time fetching wallballs off the Monster and his noodle arm was highlighted by lobbing those walls balls at a high arc back to the infield. He was the worst possible fit for Fenway, and his road OPS from Fenway before 2011 were not predictive, and shouldn't have been expected to be. I thought he was a miserable signing from the very start, and his even-worse-than-I-expected helped kick Epstein out the door at the end of the 2011 disaster.
 

lexrageorge

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Split off from the Chris Sale injury thread.

***


Carl Crawford's power was always as a dead pull hitter going to the largest right field in baseball. His speed on the basepaths was exaggerated by being able to run on Varitek's noodle arm 19 games a year. His speed in the outfield was devalued by spending all his time fetching wallballs off the Monster and his noodle arm was highlighted by lobbing those walls balls at a high arc back to the infield. He was the worst possible fit for Fenway, and his road OPS from Fenway before 2011 were not predictive, and shouldn't have been expected to be. I thought he was a miserable signing from the very start, and his even-worse-than-I-expected helped kick Epstein out the door at the end of the 2011 disaster.
Crawford had 64 SB's in 648 plate appearances against the Red Sox. I will subtract the 2 stolen bases and 8 plate appearances in his lone series against the Sox as a member of the Dodgers, leaving him with 62 SB's in 640 PA's (Salty was the Sox catcher in the 2 SB game), or about 1 in every 10.3 plate appearances.

He had 409 SB's in 5395 PA's while with the Rays, which comes out to about 13.2 PA's. So, not convinced his SB total was a function of Varitek's arm, although maybe it was slightly inflated. With the Dodgers, he had 48 SB's in 1119 PA's, or one every 23.3 PA's. He inexcusably sucked on the basepaths after the 2010 season.
 

thehitcat

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The answer is Pablo Sandoval but since we're on Carl Crawford. I got my soon to be Brother in Law both a Crawford and an AGon T-shirt jersey mockup for Christmas the year they signed. To be fair I also found him the old Guapo one for Rich Garces so I like to think I'm one for three but yeesh I bet those others are long gone to the Salvation Army.
 
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JOBU

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I’m going with Crawford for the reasons that bbjones and lexrageorge laid out very nicely. Plus he let that ball drop in front of him during the last game of the 2011 season. How you don’t lay out completely for that with the whole season on the line is beyond me. I will refrain from posting that video here because we don’t need to relive that misery again. Guy made what 30-40 million in the 1.5 years he played with Boston, in what he called “the worst time of my life”. He had a terrible attitude and never held himself accountable. Go fuck yourself Carl.

I hated Panda too but at least got a chuckle when his fat rolls blew out his belt.
 
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Sox Puppet

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Ditto on Panda. Also, let's not forget Rusney Castillo, paid $72.5M to not play for the team at all. Well, "not play" may be a slight exaggeration, but a career WAR of 1.6 is pretty sad considering the cost.
 

SawtoothPatsFan

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Has to be Carl Crawford for reasons stated previously. I didn't love the signing at the time, but it seemed (at worst) like a slight overpay for a player who, while perhaps not an ideal fit, had been a really, really good player in Tampa. Nope. Disaster pretty much from the start.

Smaller contract, but Julio Lugo has to be on the list somewhere. Maybe the Sox just shouldn't sign former Rays...
 

TapeAndPosts

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Panda edges out Hanley in the “Obviously awful contract at the time” competition.

Crawford wins the “Vastly underperforms all reasonable expectations” category,

Carl Crawford had been consistently excellent his whole career. He was coming off a 7.0 bWAR season, and he averaged 4.2 bWAR the six seasons before that, with every one of those seasons at least 4 WAR except 2008, when he was injured and “only” had 2.5. His first year with the Red Sox he was going to be 29, and while that was old enough that maybe we shouldn’t have expected 7 WAR again, he seemed a no-brainer to produce a bunch more solid seasons.

Instead in his two years with the Sox were putrid, and his slight rebound seasons with the Dodgers were still worse than anything he'd done since his rookie season. He utterly collapsed and never recovered. I didn’t want the guy, I hated him and the Rays and I never like signing the player who used to beat you, but I can’t think of anyone else who joined the Sox and just immediately fell so hard and so far.
 

Hank Scorpio

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Carl Crawford could have reasonably continued to hit around .300 with some pop, good defense, and a ton of triples and stolen bases.

Hanley Ramirez could have reasonably continued to be a great hitter while being a passable defender.

Pablo Sandoval could have reasonably continued to be an above average third baseman while being a fan favorite, despite his size.

Chris Sale was given a five year extension going into his age 30 season after a year in which he barely pitched after the all-star break due to injury and was mostly regulated to short appearances in the playoffs. And then there was the prior year when he struggled down the stretch and faltered in the playoffs. A pitcher heading into the wrong side of 30 with durability issues, a wonky delivery, and an increasing injury history. It wasn’t hard to figure out how that deal would end up.
 

Manuel Aristides

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“No one’s robbed the Sawx like that since Jack Clark!”
Makes me think of Tony Clark who, while not as catastrophic as the other guys being discussed here, was a massive disappointment. OPS+ of 47 after five years of 120-130 in DET. One home run on opening day and two the rest of the way.
 

dirtynine

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My thought was Jack Clark too - although Coco Crisp jumped to mind. I just looked it up and he “only” made $5m per in the mid 00s.
 

Didot Fromager

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Can I nominate Jose Offerman here? Bad defense, bad offense in LA, decent offense with no power and no walks in KC and a contract that goes from $2m to $5m, escalating up to $7m before we could part ways. Scale is hard to figure out but Jose is clearly a worse contract the Jack or Tony Clark, and it was clearly a bad decision when it was made.
 

Bernie Carbohydrate

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Makes me think of Tony Clark who, while not as catastrophic as the other guys being discussed here, was a massive disappointment. OPS+ of 47 after five years of 120-130 in DET. One home run on opening day and two the rest of the way.
I am fond of Tony Clark.

A. He was given the immortal nickname "Thermos" here on SoSH in 2002 because he'd stay cold even if the rest of the team got hot.

B. I figured in 2004 he'd come back to haunt us when he played for the Yankees -- and he went down meekly in the ALCS, even though Foulke was gassed and getting by on smoke and mirrors.

Agree that Crawford didn't seem a obvious fuckup at the time. We were so used to lumbering power hitters in LF I was open to the idea that this rangy speedster might bring a new dimension to the defense. He also hustled his ass off in Tampa, so I was expecting to see him take extra bases on the throw, beat out infield hits, stretch singles into doubles....

I think it is Rusney Castillo...he was so overpaid the team literally could not afford to play him. He defined negative value. At least Crawford was worth trading.

Older Division: Matt Young-- Signed for over $2 million per year ($6.3 over 3) at at time when an excellent SP (think Nolan Ryan/Dave Stewart) was $3 million per year and a decent one (think Greg Swindell/Charlie Hough) was $1.5-$2 million. Young managed 24 starts over two years, going 3-11 with a tasty 1.6 WHIP. He was so bad the Sox released him and ate the rest of the salary. He was a weird one. Somehow pitched a no-hitter. Got the yips and could not attempt a pickoff without hilarity ensuing. And $2 million was a lot of cheese back then...
 
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Jet-Boo

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The 91 free agent contracts to Jack Clark & Matt Young still make me wince. Crawford and Panda are for me the most recent debacles.
 

edoug

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Makes me think of Tony Clark who, while not as catastrophic as the other guys being discussed here, was a massive disappointment. OPS+ of 47 after five years of 120-130 in DET. One home run on opening day and two the rest of the way.
3 years later, his OPS+ was 154 in Arizona.
A. He was given the immortal nickname "Thermos" here on SoSH in 2002 because he'd stay cold even if the rest of the team got hot.
That is brilliant. Kudos to whoever came up with that. All he brought was frustration though. No real financial burden. Counting down the days 'til the Sox were free from his contract was a lot more frustrating.
 
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TonyPenaNeverJuiced

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Bobby Jenks is up there. $12m for 19 appearances plus $5.1m settlement with Mass General for messing up his bone spur surgery.
 

Tim Salmon

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I think it is Rusney Castillo...he was so overpaid the team literally could not afford to play him. He defined negative value. At least Crawford was worth trading.
Rusney is such a weird situation because the luxury tax rules changed early in his contract. The Sox kept his entire contract from counting against the luxury tax by outrighting him to Pawtucket in 2015, but putting him on the 40-man roster ever again would have resulted in an annual luxury tax hit and potential draft penalties.

The guy never had a chance to turn it around and make good on the back end of the deal, but there's at least an argument that he might have been called up and made positive on-field contributions if it weren't for the quirky luxury tax issue.

Pablo, on the other hand, was paid almost $18M/year and given enough rope to produce a negative bWAR for three years, and then the Sox had to pay about $48M more to make him go away and play for someone else. That's impressive. At least Hanley gave us 2016. Pablo gave us nothing.

It's Pablo.
 

natpastime162

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I am fond of Tony Clark.

A. He was given the immortal nickname "Thermos" here on SoSH in 2002 because he'd stay cold even if the rest of the team got hot.

B. I figured in 2004 he'd come back to haunt us when he played for the Yankees -- and he went down meekly in the ALCS, even though Foulke was gassed and getting by on smoke and mirrors.
You and I remember the 2004 ALCS far differently.
 

patinorange

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I'm in the camp that thinks one series-changing contribution that leads to a championship is enough to make almost any contract worthwhile. JD Drew, John Lackey, David Price, all earned their contracts as far as I'm concerned. Sale's 2018 contribution came before the extension, but I hold out hope that he contributes to a championship during this contract. It's just disheartening to see so much evidence that the contract is going to play out exactly like it looked like it would when it was executed.
This is where I am at. A championship is the ultimate goal and these guys made it happen.
Contracts earned. Sale? We will see.
 

ngruz25

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With all the heavy hitters already taken, I'd like to give a special shout-out to Bobby Jenks. He got $12 million over two seasons for 15 innings of 6+ ERA pitching.

He was the second highest paid member of the 2011 bullpen, trailing only Papelbon.
 

CaptainLaddie

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Not for nothing, but an aside about Carl Crawford.

He's now a music executive, and he signed Megan Thee Stallion -- if you don't know who Megan is, she's one of ten greatest female rappers of all time. He's also essentially holding her hostage on his label and she's called him a "powder head", which implies exactly what you think it implies.

He signed her to a predatory 360 deal early in her career, and she blew up well beyond anyone's initial expectations. And now... they are suing one another.

https://afrotech.com/megan-thee-stallion-carl-crawford-lawsuit?item=2
 
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jose melendez

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Not for nothing, but an aside about Carl Crawford.

He's now a music executive, and he signed Megan Thee Stallion -- if you don't know who Megan is, she's one of ten five greatest female rappers of all time. He's also essentially holding her hostage on his label and she's called him a "powder head", which implies exactly what you think it implies.

He signed her to a predatory 360 deal early in her career, and she blew up well beyond anyone's initial expectations. And now... they are suing one another.

https://afrotech.com/megan-thee-stallion-carl-crawford-lawsuit?item=2
I saw that the other day. Kind of crazy.
 

GoJeff!

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Andre Dawson was a terrible signing. 9mm for 2 years of negative WAR in 93-94. He did make the cover of the Media Guide.
 

Red(s)HawksFan

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Andre Dawson was a terrible signing. 9mm for 2 years of negative WAR in 93-94. He did make the cover of the Media Guide.
Hard to gauge from a monetary standpoint because the money was so different back then, but Lou Gorman had a long, long list of bad contract detritus on his ledgers. It's kinda incredible how many free agents he signed that were a) in their mid-30s and b) were more or less the highlight acquisitions of those winters: Dennis Lamp (35), Tony Pena (33), Jeff Reardon (34), Matt Young (32), Jack Clark (35), Danny Darwin (35), Frank Viola (32), and finally Dawson (38). However much these guys were paid, being past their prime almost guaranteed they'd be viewed as disappointments.
 

mauf

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David Price was the contract I liked least upon signing.
Me too, with Sandoval a close second.

It was clear before the ink was dry that signing Price was in lieu of keeping at least one of our young stars. That puts it ahead of Sandoval, which was a worse talent evaluation (he was declining his last two years in SF, and the Giants couldn’t wait to be rid of him), but Panda got less than half as many total dollars as Price and therefore didn’t hamstring us nearly as much.