Who Have Been The Toughest Former Red Sox To See In A Yankees Uniform?

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Saturday, December.15/2012

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By Saul Wisnia,  Red Sox Correspondent (Read his blog ‘Fenway Reflections’ here):

Pending a failed physical or other unforeseen mishap, Kevin Youkilis will be manning third base and wearing pinstripes when the Red Sox open the 2013 season at Yankee Stadium on April 1. Amazingly, it won’t be until July 19 that the teams will square off in Boston, giving Fenway Park fans their first chance to see their former favorite son in a New York uniform.

Red Sox Nation had an opportunity to adjust to life with Youk in the visitor’s dugout when the White Sox visited Fenway shortly after his trade to Chicago last summer, but this is a much different situation. Boston fans may develop a kinder, gentler hatred for the Yankees since 2004, but there is something about seeing a former Red Sox in enemy colors that still tugs at the heartstrings.

Here’s a look back at some of the biggest Boston heroes to wind up in the Bronx — and how they fared on their Fenway returns.


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He’s the guy who started it all.

When Red Sox owner Harry Frazee sold his mega-talented problem child to the Yankees for a record $100,000 in cash plus a $300,000 loan in January 1920, he did nothing to change the feelings Boston fans had toward the greatest player of all time. Ruth, Lou Gehrig, and Co. routinely plastered the hapless Red Sox of the ’20s and early ’30s at Fenway, but the crowds never stopped cheering for the Bambino.

In fact, Fenway routinely drew its biggest crowds during this period when the Yankees came to town. They knew one-of-a-kind talent when they saw it, no matter the uniform. They just wished he was still wearing the right one.


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A generation or two of readers might have never heard of this guy, but he’s in the Hall of Fame — and is the pitching equivalent of Babe Ruth when it comes to lost talent sent from Boston to New York.

The sale of Ruth started a wave of activity between Red Sox owner Frazee and his Yankees counterpart Jake Ruppert, who was more than happy to take promising players off Frazee’s hands in exchange for cold cash and warm, mostly useless bodies. The 1923 Yankees team that won the World Series had 10 players who had come directly from Boston’s roster, and by the time the right-handed Ruffing was swapped to New York for the immortal Cedric Durst and $50,000 in May 1930, the Yanks had started a dynasty and Fenway was a morgue where guys like Red came to pad their stats.

Ruffing celebrated his return to Boston a few weeks after the trade by helping the Yanks to a 3-2 victory. After going 39-96 for Boston, he would go 234-121 with New York plus 7-2 in the World Series. Guess which hat he’s wearing on his Hall of Fame plaque?


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Tom Yawkey purchased the last-place Red Sox in 1933, and apparently learned his lesson from Frazee and his other predecessors and made trades to the Yankees a rare occurrence. In fact, it wasn’t until the winter of 1972 that another swap of significance was made between the teams.

This one was another stinker.

Sparky Lyle, a left-handed pitcher who had helped the 1967 Red Sox to the pennant as a rookie and became one of the AL’s best relievers in the years that followed, was sent to New York for Danny Cater, a first baseman who looked like a used car salesman but always seemed to hit well at Fenway.

The fallout from this one was immediate. Cater hit .237 for Boston in ’72 and was out of baseball not long thereafter. Lyle had an AL-best 35 saves his first summer in the Bronx and continued his superb work with the Yanks through six more years — including a Cy Young season with the 1977 World Series champs. As a child of the Brady Bunch era I don’t recall Fenway fans booing him much, but they knew the trade wasn’t his fault.


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A lot of people forget about this one, but LOOOO-IEE was the first major star to go from the Red Sox to the Yankees as a free agent — and it didn’t hurt his reputation in Boston one bit.

A cult hero with teammates and fans who always won the big game — including three of them in the ’75 postseason — the 38-year-old Tiant was offered just a one-year contract by Boston after pitching great down the stretch of a frenzied 1978 pennant race. The Yankees dangled a two-year deal, plus other perks, and just like that one of the most popular and talented players in franchise history was gone.

It doesn’t really matter that Tiant’s best days were behind him. Seeing him in a Yankee uniform at Fenway was agony. Carl Yastrzemski spoke for all his teammates when he said that when ownership let Looie leave, “they ripped out our heart and soul.”

Fans felt the same way.


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The next marquee name to head from Boston to the Bronx as a free agent was the best pure Red Sox hitter since Ted Williams — but it was in New York he became a champion.

Third baseman Wade Boggs won five batting titles for the Red Sox, but after hitting .259 in 1992 was deemed expendable. Yanks brass thought he might still have something left, and they were right — he hit .313 over five years in New York and helped the ’96 Bombers to the World Series title. He even won two Gold Gloves, and the reception was usually mixed when he brought his slick hitting and fielding talents to Fenway.

Boston fans appreciated what he had done for them, but he was still a Yankee.


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There was no mixed reaction when it came to Roger Clemens.

There were two years (1996-97) between when Clemens left Boston as a free agent for Toronto and then moved on to the Yankees, and in that period many Fenway fans actually rooted for Roger when he came to town — starting with a 16-strikeout performance against his old mates in his first game back. The guy getting the boos that day was the guy who let him walk — Boston general manager Dan Duquette.

But once Clemens put on a Yankees uniform, the ace who won three Cy Youngs and an MVP with the Red Sox became the most despised man in the ballpark. He was even booed when introduced at the 1999 All-Star Game at Fenway as one of the century’s top pitchers, and the anger only got worse when the Rocket helped the Yanks to four pennants and two World Series titles.

Only when more than 15 years had passed and Clemens was voted on to the All-Time Fenway Team in 2012 did he hear cheers at Fenway again — and there were a few boos in there too. Given his history and the steroid rumors swirling around him, this will likely always be the case.


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First he was Jesus, then he was Judas. That just about sums up the relationship between Boston fans and Johnny Damon.

The tough, fleet center fielder was one of the key players in the Red Sox Miracle of 2004, hitting two home runs (including a grand slam) against the Yankees in Game 7 of the ALCS. He even looked the part of a biblical savior with his shoulder-length hair and long beard.

Then, after another great year in 2005, the star pupil of Scott Boras took the highest offer and signed as a free agent with New York. That’s when the “Damon is Judas” tee-shirts started popping up on Yawkey Way, and the moniker seemed even more appropriate when Steinbrenner made Damon cut off his heavy mane and beard. Johnny did get a mixed ovation on his first at-bat at Fenway with the Yanks, but by his second many fans were booing loudly.

Still, deep down it’s a good bet many of them were jeering their former rock star hero as part of the newer, more good-natured Red Sox-Yankees rivalry than pure anger. People have a much different feeling toward Damon than they do Clemens and Boggs, Had 1986 not ended as it did, perhaps this would not be the case. But it did.

Damon may have defected, but he still won’t ever have to buy a beer in Boston.



Which brings us back to Youk. Because the Yankees don’t come to Boston until July 19-21 next year (what’s up with that?) , there is a good chance that the injured Alex Rodriguez will be back manning third base for New York and Youkilis will be in a reserve role.

Still, it’s hard to imagine Youkilis won’t get at least one chance to bat during the three-game series, and as he steps to the plate he will almost surely hear the greatest cheers given a Yankee since the ovation for Mariano Rivera on Opening Day, 2005 (in thanks for helping New York blow the ALCS the previous October).

If Damon got a half-free pass for helping Boston win one World Series, Youkilis will get a full freebie for his part in two championships. Plus, more importantly, it wasn’t Youk’s choice to leave — and if most Boston fans had it their way, he and Terry Francona would both still be wearing white at Fenway.


*** The views and opinions expressed in this report are those of the author and do not necessarily reflect the views of ***

A big thank-you goes out to  Saul Wisnia for preparing today’s featured article. Saul Wisnia shares his Fenway Reflections at Born just up the street from “America’s Favorite Ballpark,” he is a former sports and news correspondent at The Washington Post and feature writer at The Boston Herald. He has authored, co-authored, or otherwise contributed to numerous books on Boston and general baseball history, and his articles and essays have appeared in Sports Illustrated, Red Sox Magazine, Boston Magazine, and The Boston Globe. His most recent book, Fenway Park: The Centennial, was excerpted on  Wisnia lives in Newton, Massachusetts, 5.94 miles from America’s favorite ballpark, with his wife, two kids, and Wally (the cat, not the Green Monster).  Feel free to follow Saul on Twitter 

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About saulwizz

I've been a member of Red Sox Nation since long before the term was coined, and currently work 300 yards from Yawkey Way. I've written for The Washington Post, Sports Illustrated, Boston Globe and Boston Herald, and have authored numerous books, including Fenway Park: The Centennial and For the Love of the Boston Red Sox. I'm currently working on Miracle at Fenway, an oral history of the 2004 Red Sox season, so if you have a story to share please shoot me an email.

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