After Babe Ruth ... who?

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


  • Total voters
    376

E5 Yaz

polka king
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The trade of Andrew Benintendi by KC to the Yankees brings up the age-old question of which former Red Sox player did it hurt the most to see in pinstripes.

I'm limiting this to the post-1967 timeframe, since few of us saw players for both teams prior to that.

And I'm also asking about players who first played for the Red Sox ... then for the Yankees. Yes, there have been players going in the other direction, but you can't say that those actually hurt to see play in New York.

Some of these guys played just briefly in New York (but I wanted to fill out the poll), but it hurt to see my childhood favorite, George Scott, end his career with the Yankees.

My answer, though, is. Luis Tiant. Yaz said that Tiant going to the Bronx ripped the heart and soul out of the Red Sox, even if Luis was in the (ahem) twilight of his career. It was very tough to see him pitch for the Yankees.

if I've missed someone you want to point out, feel free.
 
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LogansDad

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For me it was Damon. It was my mid-20's, probably the height of my baseball fandom until recently (i.e. just before my first kid was born, now they all mostly ignore me because they are teenagers so I have a little more time during my fake retired years), key part of the first WS championship of my lifetime. Then all of a sudden he's got short hair and can reach the infield from the outfield wall. It hurt, man.
 

JCizzle

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I wanted to be a contrarian that voted Youk because he's one of my all-time favorite players, but Damon leaving was the hardest one to swallow for me after '04.
 

scottyno

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Wait, Derek Lowe played for the yankees??? I had to look him up because I had 0 memory of that ever happening.

Wade Boggs on that stupid horse.
 

simplicio

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I know you're just being thorough, but Ellsbury shouldn't be on this list; the man's Yankees career is everything a Sox fan could hope for when one of our homegrown stars winds up in the Bronx.
 

Papo The Snow Tiger

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I'm going with Johnny Damon. He was one of the idiots and played a major part in the 2004 ALCS comeback and World Series Championship. He helped end the curse, and he publicly said of his impending free agency that he could never play for the yankees. He had a spot reserved for himself in Red Sox fans heaven, but then he signed with the mfy. Luis Tiant was cooked by the time he went to the mfy and at least Roger Clemens went to the Blue Jays first.

TOP 25 QUOTES BY JOHNNY DAMON | A-Z Quotes (azquotes.com)
 

Ale Xander

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There should be 2 categories, direct (Damon etc.) and delayed (Clemens)

Edit: semi-beaten by Papo
 

curly2

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As a kid who started watching baseball as Looie-mania took Boston, it's Tiant. All he wanted after 1978 -- when he pitched a two-hit shutout on the last day of the season to get the Sox in the playoff was a TWO-year contract. Heywood Sullivan and Buddy Leroux wouldn't do it. It was a gut punch to see him in pinstripes.

The most damaging was Sparky Lyle. If the Sox hadn't traded him, the probably win the division in 1972 and have a puncher's chance against the A's. And I think they win the 1975 World Series.
 

Petagine in a Bottle

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Damon, Embree, Lowe, Mientkiewicz, Myers, Youkilis, and Mendoza (edit-and Bellhorn) all ended up with the Yanks after ‘04. Olerud was the only 04 Yankee to later play for the Sox. Kind of weird but for a while the Yankees seemed obsessed with collecting these guys.

To me, this begins and ends with Clemens.
 

E5 Yaz

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I know you're just being thorough, but Ellsbury shouldn't be on this list; the man's Yankees career is everything a Sox fan could hope for when one of our homegrown stars winds up in the Bronx.
Yeah, I know. I almost added "yeah, right" after listing his name ... but there's at least one veteran poster who lamented this for years
 

kelpapa

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Damon, Embree, Lowe, Mientkiewicz, Myers, Youkilis, and Mendoza all ended up with the Yanks after ‘04. Olerud was the only 04 Yankee to later play for the Sox. Kind of weird but for a while the Yankees seemed obsessed with collecting these guys.

To me, this begins and ends with Clemens.
Bellhorn too.
 

djbayko

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This is a difficult question for me to answer. Besides the fact that I'm a little too young for a couple of those guys, my image of the others has been permanently tainted by them having gone to the dark side. I just stopped caring about them, so it's difficult to remember how disappointed I was.

I guess maybe Damon because he was a very lovable one of "The 25". It's either him or possibly Clemens because when I was young, innocent and really into baseball, he just seemed to dominate every time he pitched, and I followed him religiously. Of course, his stint in Toronto made it so that I was already upset, so his going to the Yankees didn't sting quite as much.
 

soxin6

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I voted for Damon because he left the Sox for the Yankees after being part of the 04 team that vanquished them and ended the curse. If Clemens hadn’t gone to Toronto first it might have been him, but after being with the Jays it stung less.
 

Deweys New Stance

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Yeah I had zero memory of Lowe in pinstripes. Only 23 innings, but he actually saved a game for them.

I voted Tiant because:

a) He had been such an iconic and beloved member of the team for eight seasons, particularly for his pitching in the '75 Series
b) It came just over a month after the trauma of the '78 season and losing the one game playoff to the MFYs
c) Even though he was 38 years old, I couldn't believe those idiots Sullivan and LeRoux would actually let him get away, period, let alone to the MFYs
d) I was 14 years old, and took these things a lot harder

And then this troll job really annoyed me:
53681
 

Mueller's Twin Grannies

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Dec 19, 2009
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Clemens forced his trade to the Blue Jays based on a purposefully misconstrued comment from Duquette, then suddenly got into shape and turned into a true ace again before engineering another deal to the Yankees based on a clause he forced Toronto to put into his deal with them to allow him to force a trade if the Jays continued to go nowhere, which he smartly bet on them not doing.

How anyone could be sad to see him in pinstripes is beyond me. He manifested his own path to New York, by design, and was a major cog in their dynasty. If anything, seeing him in a Yankees uniform should have made people mad at him.

Tiant just wanted another decent contract to finish out his career, and hopefully get a ring, in Boston, and ownership gave him the finger. He gets my vote.
 

E5 Yaz

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Surprised to see Clemens with the early lead. I would've thought he'd burned his bridges at that point
 

Papo The Snow Tiger

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I think if you're a Red Sox fan up at this time of night reading a thread about the pain of seeing a former beloved Red Sox player going to the mfy you're probably not feeling too good about things right now. I know I was bumming out. Then I decided to surf YouTube and I came across this gem.

View: https://www.youtube.com/watch?v=SJUhlRoBL8M


At least the Royals should be a weaker team without Benny when the Sox play them in August and may actually have a chance at winning a game.
 

Ale Xander

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Oct 31, 2013
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I think if you're a Red Sox fan up at this time of night reading a thread about the pain of seeing a former beloved Red Sox player going to the mfy you're probably not feeling too good about things right now. I know I was bumming out. Then I decided to surf YouTube and I came across this gem.

View: https://www.youtube.com/watch?v=SJUhlRoBL8M


At least the Royals should be a weaker team without Benny when the Sox play them in August and may actually have a chance at winning a game.
August AND September
 

OnTheBlack

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Dec 23, 2020
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There are only two answers to this imo. Damon and Clemons. Clemons actually dealt damage to the home team from the opposite trench, Damon willingly defected from the team that slayed the dragon after he said he would never.

Damon is Benedict Arnold for me.
 

Daniel_Son

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I could be misremembering things, but I seem to recall a lot of talk on here about how Benny's swing would benefit greatly from a shorter right field. I voted Damon because he was such a huge part of the 04 team and expressed disdain for the Yankees before signing there. But if Benny leads them to another title, I suspect that answer would change.

EDIT: Finally got in front a computer this morning. Here's Beni's spray chart data for 2022 laid against toilet bowl dimensions. If I'm counting correctly, he'd already have 20-25 home runs. I have a feeling we're going to really start disliking him in a few weeks.

53703
 
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jmcc5400

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Surprised to see Clemens with the early lead. I would've thought he'd burned his bridges at that point
He had. It didn’t hurt because he was “ours.” It hurt because it was emblematic of the MFY’s all-consuming gluttony at that point in time. There’s a reason that Game 3 of the ‘99 ALCS was so cathartic.

In terms of pure “sadness,” the answer for me is Tiant, who was beloved in this town in a way that Clemens, even at his height, never was.
 

Van Everyman

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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 …
 

Kliq

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I'm too young for anyone pre-Damon to really sting. Even Damon, he wasn't like Papi or Manny or Pedro, and the hatred for him going to NY always struck me as a tad contrived.

I completely forgot about Youk going to the Bronx. Youk was a classic popular guy that isn't a HoF but a loveable player special to the local fanbase. This is just wrong:
 

Attachments

DontTauntOrtizMe

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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 …
You’re clearly raising her well. I only hope my kids would be that pissed off about a trade when they are her age.
 

catsooey

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Jun 27, 2019
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Really pissed about the Benny trade, but for me it was Clemens. I’m 43 so my Sox fandom started with the 80’s team. Jim Rice, Dewey Evans, um Bill Buckner (great player aside from that one time..), Oil Can Boyd, Jerry (RIP), Eck, Al Nipper, Bruce Hurst, ‘The Steamer’ Bob Stanley (he signed my little league hat in the stands before a game in ‘86). And Clemens was a god. And to add insult to injury, part of him getting sent to the Yankees meant having to hear clips of Susan Waldman screaming her head off about behind- the-scenes intrigue of “Roger Clemens being somewhere outside George Steinbrenner‘s office!” (or something).
 

Lose Remerswaal

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There are only two answers to this imo. Damon and Clemons. Clemons actually dealt damage to the home team from the opposite trench, Damon willingly defected from the team that slayed the dragon after he said he would never.

Damon is Benedict Arnold for me.
This is my feeling. Adding Lyle as the one that really hurt the most competitively since this was a CHOICE by management to send him To the MFY
 

Philip Jeff Frye

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Easily Luis Tiant. He was the heart and soul of those almost great 70s Red Sox teams. It would have been like Big Papi signing with the Yankees. That it happened a few weeks after Bucky Fucking Dent made the wound even more raw.

His departure was also the harbinger of a lot of Red Sox talent leaving because the team was too stupid and cheap to sign them.
 
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wiffleballhero

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If you are of a certain age for this list, it is clearly Tiant. What a trauma.

What does it even mean to be on a team if you can up and go join your enemies? Rocked my little 6 YO world. I didn't even like seeing Bill Lee in a Montreal uniform. Still don't.
 

Remagellan

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Yeah I had zero memory of Lowe in pinstripes. Only 23 innings, but he actually saved a game for them.

I voted Tiant because:

a) He had been such an iconic and beloved member of the team for eight seasons, particularly for his pitching in the '75 Series
b) It came just over a month after the trauma of the '78 season and losing the one game playoff to the MFYs
c) Even though he was 38 years old, I couldn't believe those idiots Sullivan and LeRoux would actually let him get away, period, let alone to the MFYs
d) I was 14 years old, and took these things a lot harder

And then this troll job really annoyed me:
View attachment 53681
This, exactly. If you lived in the NYC media market, having to see these commercials so soon after the collapse of '78 was devastating.
 

3Olympics

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Aug 1, 2019
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For me, it is easily Damon. Especially because, in the aftermath, he has been, quite appropriately, lost to RSN and because he went from being a leading Idiot to being a colorless cog in the machine.
 

mauf

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Clemens and Damon are the only two I even cared about.

The early ‘90s Yankees that Boggs joined sucked. The Ellsbury contract was insane the moment it was inked. I’m too young to remember Lyle and Tiant. Benintendi never would’ve turned it around here. The others all were cooked by the time they put on pinstripes.

I surprised myself by being capable of thinking less of Clemens than I did during his Toronto stint, but it’s Damon for me. He personified why that 2003-05 team was something that never could have happened in New York; most obviously because of the hair, but the hair was indicative of his entire persona, which would never have played on the Most Corporate Franchise in Pro Sports. I never hold a grudge against athletes for taking the biggest pile of money on the table, but when Damon went to New York and fell in line, he revealed that the character he played in Boston was merely that — a character. I’m not angry about it, but I obviously don’t feel the same way about him that I did when I thought that person was his authentic self.
 
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pedro1918

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I never hated Tiant. I was crushed when he left, but I never hated him. I always blamed the team more than him.

To this day, the sight of Clemens makes me barf. I can not listen to the broadcast when he is on. I’m an older man now. It’s really something I need to work on.

But anyway, it’s Clemens.
 

Van Everyman

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I wasn’t entirely crushed when Damon left for the Yankees. Much harder for me as a fan was when he helped the Yankees win their only ring of the 2000s and then refused a trade back to the Sox (from Tampa?) when he had a chance to end his career with us. So the body snatching was complete.
 

DJnVa

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The early ‘90s Yankees that Boggs joined sucked.
Did they?

The NYY teams Boggs played for went:

1993: 88-74
1994: 70-43 (best record in AL)
1995: 79-65-1 (postseason)
1996: 92-70 (won the Series)
1997: 96-66 (postseason)
 

SinkingLowe

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Wade Boggs leaving was the hardest one for me for many reasons. All of those reasons came flooding back when I saw Boggs a few times in Cooperstown last weekend. I learned about baseball and became a Red Sox fan in the early-mid 80s and Boggs was a cornerstone of the franchise. In 89 when he got his 200th hit (for the 7th year in a row) my dad was supposed to take me to the game but he and my mom had a huge fight ending with my dad running off to some bar, leaving me to listen to the game on the radio in my bedroom. So when Boggs left Boston a few years later it hurt on a level that seemed deeper than just a ball player leaving town.

(And now I'm off to my therapist to unpack the psychological damage of my dad and Wade Boggs leaving town).
 

RG33

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I’m still not over the Texas Con Man going to the Blue Jays, nevermind the Yankees.
 

BaseballJones

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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.
 

drbretto

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I am guessing if I was about 10 years older, it would have been Clemens and/or Boggs. But it ends up being Damon because that was more my era. Dude straight up said he never would and then just did.