After Babe Ruth ... who?

Which former member of the Red Sox hurt the most to see in Yankee pinstripes?


  • Total voters
    376

bosockboy

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Jul 15, 2005
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Damon didn’t bother me terribly. The Sox didn’t want to pay him, and the Yankees had every right to sign him. Winning in 2007 validated most of their post 2004 decisions.
 

troparra

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Jan 3, 2007
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It's so weird but this Benintendi one stings. I know the Sox traded him away, and then he was traded to NY, so it's not like he went there as a free agent. But still...you just KNOW he's gonna rake for them and it's going to be incredibly painful to watch. And I always liked him and wanted him to succeed here.
Well, he's got 3 home runs in 390 PAs so far this year, which means he'll hit about 20 for the Yanks the rest of the season.
 

donutogre

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Voted Damon, but yeah if I was a bit older I'm sure it would be Clemens. I was 25 when he jumped ship and was living and breathing the Red Sox at the time. Even then, I knew it was a business and that guys were going to do what they had to do... but it's not often you hear someone literally say that they wouldn't go to the Yankees and then do exactly that. As others have said, he could have been a legend for life here, and now he's just... another old ballplayer.
 

chawson

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It's so weird but this Benintendi one stings. I know the Sox traded him away, and then he was traded to NY, so it's not like he went there as a free agent. But still...you just KNOW he's gonna rake for them and it's going to be incredibly painful to watch. And I always liked him and wanted him to succeed here.
I doubt he’ll rake, but he may poke enough soft liners to right to keep hitting .300. I felt certain Beni would become a Yankee. Was never really in on him as a Sox but can understand how it stings.

Clemens for me. I idolized him as a young kid. As a teenager I checked out of baseball for a half-decade or so, during Clemens’ Toronto and early Yankee years. When I came back it felt akin to a lesson about the harsh realities of adulthood.

I think the Yankees like to do this sort of thing when it makes sense. It riles up their fanbase and demoralizes (some of) ours, sowing another ripple of chaos through our media feedback loop. I don’t even think it’s petty; it can be a smart tactic.
 

brs3

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May 20, 2008
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Clemens stung the most, not even because I enjoyed watching him. My fandom came alive with the '97 team, so it had more to do with him being SO GOOD with Toronto and then the Yankees, and at the time there was no comeback to the jokes from MFY fans. The few years(ok, all the years) leading up to 03/04 is something younger Sox fans cannot possibly understand,
 

Philip Jeff Frye

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Oct 23, 2001
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I can't understand the Benintendi angst. Didn't seem like anybody was particularly sad to see him go when he was traded. He was a decent player for us, particularly in 2018, but was he a real difference maker? It's not like he turned his back on us to directly join the Yankees like Damon, Ellsbury or Tiant did.

I'd feel a lot more angst right now if the Yanks had acquired Soto last night.
 
Went with Boggs.
I'm one of those for whom it stings less when there's a team in between. Like, it's not directly the Red Sox fault. So I could live with the Clemens thing.
I was young for the Tiant deal, and I don't recall him being especially good in NY (even though that's not exactly right, as his first year there was solid). It just didn't get under my skin. (Even though NY wasn't involved, I was much more upset when Lynn was gone...and Fisk, for example.)
Damon was tough. I was outraged, but it wore off. Everything was a little lighter after '04.
But Boggs. And (to echo it again)...that horse. The success he had. Plus, he kinda had that unappealing side that it sucked to even let yourself see. I could hate myself for ever having liked him and also wish he was still playing for the Sox. (Like Clemens, but Totonto in between softened the blow.)
 

8slim

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Nov 6, 2001
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Tiant, Lyle and Scott pre-date me, so it's Damon, easily. I just couldn't believe that THAT GUY from the '04 team would scurry off to the Yanks. And I was young enough then to still get worked up about such things.

I hated Clemens more with the Jays, after he decided to get himself in better shape and pitched lights out for them. I mean I hated him when he was with the Yanks too, but I was used to hating him by the time he got there.

I didn't really care when Boggs left for NY, because we had Scott Cooper to replace him after all (yeesh). But I do still get annoyed seeing pictures of him on the horse.
 

joe dokes

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Jul 18, 2005
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Boggs and the horse probably got me more than the others because he just wasn't that good with NYY, other than the strike year. It would have been more fitting for the horse to be dragging his carcass across the field, like his teammates did.
Damon was far too dumb for me to hate.
 

ngruz25

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Sep 20, 2005
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Damon was an absolute rock star in Boston in 2004. He had the hair, the nickname, the bestselling book... after the big three of Pedro, Papi, and Manny, he was easily the most popular player on the team. He could have set himself up for a lifetime of throwing out first pitches and popping into the NESN broadcast booth and glad handing his way around Fenway once a year.

Instead, he opted for $52 million and pariah status in Boston. I really wonder if the few extra million he got from New York was worth the lifelong celebrity status he gave up in Boston.
 

donutogre

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Damon was an absolute rock star in Boston in 2004. He had the hair, the nickname, the bestselling book... after the big three of Pedro, Papi, and Manny, he was easily the most popular player on the team. He could have set himself up for a lifetime of throwing out first pitches and popping into the NESN broadcast booth and glad handing his way around Fenway once a year.

Instead, he opted for $52 million and pariah status in Boston. I really wonder if the few extra million he got from New York was worth the lifelong celebrity status he gave up in Boston.
Judging from the way he kept bringing it up for the rest of his career (if I'm remembering correctly, anyway), I'm gonna wager no.

I will say that the fact that '04 happened made the Damon situation sting a LOT less... though if they didn't win with him, it wouldn't have been all that big of a deal if he left for NY. The Clemens stuff all happening before the Sox managed to win one makes it that much worse. Just glad it wasn't so much on my radar when it happened :)
 

Smiling Joe Hesketh

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It's so weird but this Benintendi one stings. I know the Sox traded him away, and then he was traded to NY, so it's not like he went there as a free agent. But still...you just KNOW he's gonna rake for them and it's going to be incredibly painful to watch. And I always liked him and wanted him to succeed here.
I’m here as well. It doubly stings because in 2018 he looked to be a building block for years to come. Now the Sox are below .500 and in last place, the guy we traded Benintendi for can’t play, and Benintendi is now a Yankee and is going to play a big role
in any success they have this year.

Emotionally it’s a a really shitty feeling and feels like being kicked when we are down.
 

BaseballJones

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I’m here as well. It doubly stings because in 2018 he looked to be a building block for years to come. Now the Sox are below .500 and in last place, the guy we traded Benintendi for can’t play, and Benintendi is now a Yankee and is going to play a big role
in any success they have this year.

Emotionally it’s a a really shitty feeling and feels like being kicked when we are down.
That 2018 outfield....

LF - Benintendi (23): 579 ab, 103 r, 41 2b, 6 3b, 16 hr, 87 rbi, 21 sb (3 cs), .290/.366/.465/.830, 123 ops+, 4.8 bWAR
CF - Bradley Jr (28): 474 ab, 76 r, 33 2b, 4 3b, 13 hr, 59 rbi, 17 sb (1 cs), .234/.314/.403/.717, 92 ops+ , 2.5 bWAR
RF - Betts (25): 520 ab, 129 r, 47 2b, 5 3b, 32 hr, 80 rbi, 30 sb (6 cs), .346/.438/.640/1.078, 186 ops+ , 10.7 bWAR

Best defensive outfield probably in Red Sox history. Other than Bradley's low avg and obp, they were really good at the plate too. And all young. Looked like they were going to have a legendary outfield for many, many seasons.

-sigh-
 

Rovin Romine

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I can't understand the Benintendi angst. Didn't seem like anybody was particularly sad to see him go when he was traded. He was a decent player for us, particularly in 2018, but was he a real difference maker? It's not like he turned his back on us to directly join the Yankees like Damon, Ellsbury or Tiant did.

I'd feel a lot more angst right now if the Yanks had acquired Soto last night.
I'm certainly in your boat. It's puzzling to me.
 

BoSox Rule

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Jul 15, 2005
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Clemens is the biggest asshole to ever do it but he wasn’t the same pitcher for the Yankees and his replacement pitched the greatest two seasons in history during Clemens’ first two seasons in New York
Damon is my answer because the rivalry was at its height, he was still good, and said he was never going there

Can’t have any ill will towards players like Youkilis and Lowe who were either largely irrelevant by the time they got to New York and we’re traded away and downhill with no interest from the Red Sox when they departed.
 

JoePoulson

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It'll always be Wade Boggs for me. By far my favorite active player growing up (Teddy always will be my all-time fave), I hit left-handed so I emulated Boggs whenever I could. The Margo stuff was shitty obviously but to a younger me him going to the Yankees was devastating. And then the horse, as others have mentioned. Brutal.

Edited to add - then he went to the Rays! Like a double-whammy of suck that completely wiped me out of even collecting his cards again. Although the Always Sunny episode with him is incredible.
 

John Marzano Olympic Hero

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It's Clemens for me and no one else is particularly close. The 86 Red Sox was the team that got me head-over-heels into baseball and Clemens was the main reason for it. I bought a Clemens rookie that summer ($15 for a baseball card!), I got one of those old Sports Illustrated Roger Clemens poster for my wall, I was all-in on Roger Clemens. As the years progressed and he would say something dumb or shit the bed in the playoffs, he was still my guy. Then he struck out 20 Tigers and left for Toronto a few months later, to be closer to his family in Texas, of course.

And it was fine. He was a Blue Jay and they paid him a lot of money and plus he was kind of winding down his career and it was fine. Just fine.

Then he engineers a trade to the Yankees and it was like, "The fuck are you doing?" and he just lapped up all of that Yankee bullshit and it was not good. It was weird seeing him in pinstripes.

The others? Whatever. Youkilis and Lowe were done, Lyle, Tiant and Scott were before my time, Ellsbury was an albatross and Damon was a mercenary. When Boggs left, people around here held the door for him. No one cared. I remember that when EEI flipped to 24-hour sports format, the morning show had a segment called "Wade Watch" and they'd talk about how well Boggs was hitting and goof on him. The prevailing wisdom was that he was washed up and it was time for the Scott Cooper era to begin. The other thing about Boggs is that there was a new rumor every week about him getting traded somewhere since the Margo Adams thing happened in 1989 (88?), so him leaving was never really a huge shock. I think that Sox fans had been bracing for his inevitable departure for years.
 

BaseballJones

ivanvamp
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Oct 1, 2015
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The others? Whatever. Youkilis and Lowe were done, Lyle, Tiant and Scott were before my time, Ellsbury was an albatross and Damon was a mercenary. When Boggs left, people around here held the door for him. No one cared. I remember that when EEI flipped to 24-hour sports format, the morning show had a segment called "Wade Watch" and they'd talk about how well Boggs was hitting and goof on him. The prevailing wisdom was that he was washed up and it was time for the Scott Cooper era to begin.
That's two-time AL All-Star Scott Cooper, my friend.
 

moretsyndrome

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I know, he's probably a jerk and I love Luis and still get pissed about Lyle/Cater, but it's Clemens. Well inside the ten most important players in team history. Hated seeing him in NY.
 

moondog80

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Sep 20, 2005
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Would we trade Frenchy and Winckowski for the guys the Royals got?
 
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Was (Not Wasdin)

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That 2018 outfield....

LF - Benintendi (23): 579 ab, 103 r, 41 2b, 6 3b, 16 hr, 87 rbi, 21 sb (3 cs), .290/.366/.465/.830, 123 ops+, 4.8 bWAR
CF - Bradley Jr (28): 474 ab, 76 r, 33 2b, 4 3b, 13 hr, 59 rbi, 17 sb (1 cs), .234/.314/.403/.717, 92 ops+ , 2.5 bWAR
RF - Betts (25): 520 ab, 129 r, 47 2b, 5 3b, 32 hr, 80 rbi, 30 sb (6 cs), .346/.438/.640/1.078, 186 ops+ , 10.7 bWAR

Best defensive outfield probably in Red Sox history. Other than Bradley's low avg and obp, they were really good at the plate too. And all young. Looked like they were going to have a legendary outfield for many, many seasons.

-sigh-
Benintendi put those numbers up while making 650k, which might have made him the best bargain in the league that year.
 

SoxFanInPdx

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Clemens for me by a mile. I grew up adoring that guy. Now, the sheer sight of him puts me in a bad mood. When he was in the NESN booth not long ago this season, I flat out went out for a long walk. Wanted no part in subjecting myself to that.
 

Petagine in a Bottle

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Jan 13, 2021
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Would we trade Frenchy and Winckowski for the guys the Royals got?
Seems like the answer is probably yes. Franchy seems like a possible non tender. Winckowski appears to have a limited ceiling with his lack of strikeouts, IMO. None of the other guys acquired are even among the Sox top 50 prospects. The guy the Sox got from the Mets, Freddy Valdez, was in the Mets top 20 and was expected to hit for power but hasn’t yet. De La Rosa is in the FCL but hasn’t pitched much; and the other guy Grant Gambrell has been awful and is now injured.
 

CarolinaBeerGuy

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It’s Clemens for me, easily. He was my favorite player as a kid and my Sox-loving uncle nicknamed me Rocket. Being a kid growing up in North Carolina during his prime years in Boston, I didn’t know he was a huge asshole.
 

Ale Xander

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That's two-time AL All-Star Scott Cooper, my friend.
That's back to back AL All-Star, and lone RS rep both times. Those were the dark years.

Then Mo made the Leap, 3 top-5 MVP finishes and a win in 4 years, and franchise turned around. (Thanks, Pedro/Duq)
 

Ferm Sheller

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For me, it was Clemens and Boggs as they were "childhood heroes" (and for some reason I think Boggs bothered me more, but it's close).

I'm too young to have been bothered by the Ruth trade when it happened . . . and for that matter, also the additions of Lyle, Tiant, and Scott to the Yankees's roster.
 

Petagine in a Bottle

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You wonder if the Sox would have let Boggs go if advanced metrics were more of a thing in 1992.

He had a .261 BABIP that year, which was 45 points lower than any other season in his career. Such a fluky bad year at the wrong time.
 

moondog80

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Sep 20, 2005
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I'm not on high Winckowski; I still trust Chaim but it is tough to see Renfroe and Beneintendi out there having good seasons for relatively small $$ given the state of our OF. Alex Binelas, all my hopes lie on your shoulders.
 

BaseballJones

ivanvamp
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That's back to back AL All-Star, and lone RS rep both times. Those were the dark years.

Then Mo made the Leap, 3 top-5 MVP finishes and a win in 4 years, and franchise turned around.
Ha yeah. Here's a Cooper-Boggs comparison in Cooper's all-star seasons (by the way, for a name that seems as common as "Scott Cooper", he's the only MLB player on baseball-reference with that name...color me surprised by that):

1993
Cooper: 67 r, 147 h, 9 hr, 63 rbi, .279/.355/.397/.752, 98 ops+, 3.0 bWAR
Boggs: 83 r, 169 h, 2 hr, 59 rbi, .302/.378/.363/.740, 104 ops+, 4.3 bWAR

1994
Cooper: 49 r, 104 h, 13 hr, 53 rbi, .282/.333/.453/.786, 98 ops+, 1.9 bWAR
Boggs: 61 r, 125 h, 11 hr, 55 rbi, .342/.433/.489/.922, 142 ops+, 4.5 bWAR

So even at Scott Cooper's very best, he wasn't close to as good a player as Wade Boggs was, even in some of Boggs' more pedestrian seasons.


BTW, what the hell happened to Boggs in 1992? Until then his career slash line was .345/.435/.471/.906, 146 ops+. Then all of a sudden in 1992 he puts up this slash line: .259/.353/.358/.711, 96 ops+.

Crazy.

EDIT: Oh @Petagine in a Bottle answered this question above....it was Boggs' crazy low BABIP that year. Ah.
 

snowmanny

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I voted Tiant on impulse but give me more time to think about it, say a couple of years, and the answer is probably Devers.
 

yalesoxfan

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I find them all irritating because it has been mostly a one way street from the Red Sox to the Yankees. I’m guessing Yankees fans watching Cone, Wells, or Henderson on the Sox at the end of their careers wasn’t the same as a Boggs, Clemens, or Tiant.
 

Red(s)HawksFan

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You wonder if the Sox would have let Boggs go if advanced metrics were more of a thing in 1992.

He had a .261 BABIP that year, which was 45 points lower than any other season in his career. Such a fluky bad year at the wrong time.
I thnk if they had hired Duquette a year sooner, Boggs goes nowhere. Lou Gorman was an old school guy and nothing demonstrated he was at the end of the line as a useful evaluator/builder of a roster than that 92-93 off-season where he let Boggs walk away so he could sign a clearly past-his-prime Andre Dawson instead. I also wouldn't discount Gorman being a stubborn son of a bitch who let Boggs go in order to promote Scott Cooper so he could be vindicated for choosing to trade Bagwell instead of Cooper for Larry Anderson. There were rumors that the Astros asked for Cooper and Gorman offered Bagwell as an alternative thinking Cooper the better prospect.
 

Mugsy's Jock

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I clicked before reading any of the comments, figuring I'd be the only one to vote for Loooie. Lo and behold, he's a pretty popular choice.

If you didn't live through the Sox in the 70s, you can't appreciate the combination of personality and results (including on the biggest stage) Tiant brought to the team. Trying to think of a corollary, the first name that popped to mind was the Celtics' Isaiah Thomas -- but Isaiah didn't last as long as Tiant and he didn't have as many opportunities in do-or-die games with a championship-level (if not championship) team.

As great as Sparky was on the MFY, he didn't exactly make a major mark on the Red Sox over several years. Or maybe I was too young to remember.

Boomer was my first favorite player, but I was more bummed when he was traded to the Brewers than when he just played out the string in New York.

I love Lowe and Youk, but again, their Yankee years weren't significant enough to piss me off.

Clemens, Damon, Ellsbury and Boggs were tremendous Red Sox and great Yankees as well (okay, just for one year for Ellsbury, but he did make a difference that year), but there were things about each of them that rubbed me the wrong way. Wasn't hard to learn to hate them. That was never the case for Looie.
 
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jon abbey

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I find them all irritating because it has been mostly a one way street from the Red Sox to the Yankees. I’m guessing Yankees fans watching Cone, Wells, or Henderson on the Sox at the end of their careers wasn’t the same as a Boggs, Clemens, or Tiant.
Whitlock! :)
 

Doug Beerabelli

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I’m mad at my 15 year old Sox-loving daughter because she got COVID this week by being an irresponsible 15 year old. So right before she went to bed tonight when I was doing the dishes downstairs and she was brushing her teeth I said, “Want to hear something that will really ruin your night? Benintendi just got traded to the Yankees.”

She said “Are you freaking KIDDING me?”slammed the door and went to bed.

So, Beni …
LOL. My 21 year old daughter texted me this morning from VT her lament that Beni was a Yankee. He was her first dreamy Red Sox crush, although she and Varitek share a birthday.

I'm still voting Tiant.
 

Shaky Walton

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Damon. Not so much as for him personally as for the fact that a key member of the 2004 sportsgasm joined those Motherless Fucks.

Clemens was bad but I never identified with him personally like I did with Manny, Ortiz and Pedro. If any of them had jumped to NY, I would have done something drastic.