The 15 Worst Transactions in Yankee History

#3 | Buhner in pinstripes. It still hurts to look at this.

With 45 days until pitchers and catchers report, we’ve gotta talk about something, right?

Some of the greatest players in Yankee history, men who fortified Yankee dynasties, were brought to the Bronx through trades and acquisitions.  Babe Ruth, Paul O’Neill, Goose Gossage, Reggie Jackson, Catfish Hunter, and CC Sabathia are just a handful of Yankee legends that did not come up through the vast farm system.  However, not every transaction has worked out as well as Red Ruffing or Roger Maris.  Here are the 15 worst moves in Bomber history.

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#15 | Randy Johnson | 1/3/2005

Johnson came to New York from Arizona for Javier Vazquez, prospects, and cash.  At first glance the Big Unit’s 2 seasons in New York hardly look like a bust: 34-19/4.37 ERA/383 strikeouts.  Johnson was effective in 2005 with a 17-8 record and 211 strikeouts, 2nd-most in the AL, but 2006 was another story as he won the same number of games yet saw his ERA balloon up to 5.00, the highest of his career.  However, Johnson saved his true ineptitude for the postseason.  Once regarded as one of baseball’s premier big-game pitchers, Johnson was abysmal in 2 postseason starts for New York.  Against the Angels in the 2005 ALDS, he lasted just 3 innings after yielding 9 hits and 5 runs as the Yanks lost a pivotal Game 3.  In the 2006 ALDS vs. Detroit the Big Unit again got the ball in Game 3 but did not fair much better, giving up 8 hits and 5 runs in 5.2 innings.  The fact that he earned $31.7 million while in pinstripes just adds insult to injury.

#14 | Larry Gura | 5/16/1976

Larry Gura went to the rival Kansas City Royals in 1976 in exchange for Fran Healy whose career in pinstripes lasted just 3 years.  He played in 74 games for New York, mostly when Thurman Munson needed a day off, and batted .250 with 0 home runs and 16 RBIs.  Meanwhile, Gura would play for 10 years in Kansas City, racking up 111 wins and a 3.72 ERA while wearing powder blue.  He also finished in the top 10 of the Cy Young Award vote 3 times.  It hurts even more that he beat the Yanks in the ’78 and ’80 ALCS.

#13 | Tommy Holmes | 2/5/1942

When Buddy Hassett came to New York from the Boston Braves, the Yanks believed they had landed a bat to fill the hole left by Lou Gehrig.  However, Hassett played just 1 year in New York before being drafted into the war and never playing baseball again.  In his only season he batted .284 with 5 home runs and 48 RBIs.  The Braves got the better end of the deal as they picked up Tommy Holmes, a prospect the Yankees jettisoned because they were overwrought with outfield talent.  Holmes played in Beantown for 10 seasons, batting .303 during that span, finishing in the top 10 in batting average 5 times.  In 1945 he finished 2nd in the MVP vote while becoming the only player to lead the league in home runs (28) and strikeouts (9).  Had the Bombers not won 4 World Series titles and 5 pennants in the 40s this trade might be higher on the list.

#12 | Armando Benitez | 7/16/2003

I hated Armando Benitez for ruthlessly beaning my favorite Yankee, Tino Martinez, in the back in 1998, unleashing one of the most vicious brawls in recent memory.  I hated him when he was the Mets’ closer and relished in his blown save in Game 1 of the 2000 World Series.  So when the Yankees acquired him from the Mets, ignoring his nickname “Blownitez,” I was livid.  I remember staring down at the back page of Newsday in disbelief.  How could we bring this anti-Yankee into the fold?  Mercifully, his time in pinstripes lasted just 9.1 innings, but not before he lost a game for us.  The Yanks shipped him off to Seattle on August 6th for Jeff Nelson.  It remains one of the stranger trades I can remember.

#11 | Steve Trout | 7/13/1987

When George Steinbrenner acquired Trout for Bob Tewksbury, Rich Scheid, and Dean Wilkins he thought he’d secured the pennant.  Things didn’t pan out that way.  Trout went 0-4 in 9 starts with a grotesque 6.60 ERA and walked 10 more batters than he struck out.  Tewksbury wasn’t much better for the Cubs, but after moving to St. Louis in 1989 he displayed the prowess the Yankees believed him incapable of.  In 1992 he was an all-star and finished 3rd in the Cy Young voting with a 16-5 record and a 2.16 ERA.

#10 | Kevin Brown | 12/13/2003

By the time Kevin Brown arrived in New York from the Dodgers he was a 39-year-old, eviscerated husk of his former self, but we got him in exchange for Jeff Weaver, so I was still optimistic.  His 2004 season began with promise as he posted a 10-4 record, but he missed the remainder of the regular season after punching a clubhouse wall in early September.  He did come back just in time for the playoffs and had a great start in the ALDS, but his 2 outings in the ALCS were so putrid that they almost single-handedly awoke Boston’s championship mettle after 86 years of slumber.  In his two starts he lasted a total of 3.1 innings while yielding 8 runs.  The Sox should have given him a ring for his efforts.  Then, he further proved a wall was the only target he could hit anymore, posting a 4-7 record in 2005 with the worst ERA of his career: 6.50.  Not surprisingly, it would be his last season in baseball.

#9 | Esteban Loaiza | 7/31/2004

The thing that aggravated me about Loaiza was that he never seemed particularly upset about how awfully he was pitching.  He started just 6 games as a New York Yankee and was 1-2 with an 8.50 ERA before being banished to the bullpen.  For his services we sent Jose Contreras to the White Sox.  The Cuban defector was far from a reliable starter while in New York, but he was very effective for Chicago, helping them win the 2005 World Series.

#8 | Jeff Weaver | 7/5/2002

Jeff Weaver was just as temperamental as his brother Jered, but Jered could pitch.  In 1 1/2 seasons in the Bronx, Weaver went 12-12 with a 5.35 ERA, which included a 7-9 mark and 5.99 ERA in 2003.  However, his most dubious moment as a Yank was giving up a walk-off home run to Alex Gonzalez in Game 4 of the ’03 Fall Classic that made the series 2-2 instead of 3-1 in favor of the Yanks.  For the pleasure of watching him consistently melt down, we sent Ted Lilly to Oakland where he pitched effectively for the A’s before becoming an all-star for the Blue Jays and the Cubs.

#7 | Javier Vazquez | 12/16/2003 & 12/22/2009

I remember yelling at the TV, “WHY?!  WHY?!”  The Yanks brought Vazquez in from Montreal for Nick Johnson, Randy Choate, and Juan Rivera as a possible replacement for Andy Pettitte.  He wasn’t.  He went 14-10 with a 4.91 ERA, but was especially nauseating in the postseason, yielding 12 runs in 11.1 innings of work including a 1st-pitch grand slam to Johnny Damon in Game 7 of the ALCS (and 3 of those runs were charged to Kevin Brown).  When we sent him to Arizona after the season I thought we were done with him, but Vazquez proved to be a nightmarish boomerang, returning in 2010 to post a 10-10 record and a 5.32 ERA.  I’m still nervous that he may come out of retirement just to haunt me again.

#6 | Mike Lowell | 2/1/1999

In 1998 Lowell was a promising prospect that saw just 8 games of action for the best team in American League history.  However, with World Series MVP Scott Brosius at 3rd base, Lowell became a tradable commodity.  So he was sent to Florida for Todd Noel, Mark Johnson, and Ed Yarnall.  Who?  Exactly.  Lowell blossomed into a very productive batter, hitting 32 homers and knocking in 105 RBIs for the ’03 Marlins that beat the Yanks in the World Series.  He then moved to Boston where he batted .324 while notching his 3rd 100-RBI season in helping the Sox to a World Series crown.  He would retire as a 4-time all-star and a Gold Glove winner.

#5 | Carl Pavano | 12/20/2004

Carl Pavano symbolized an era between championships in which the Yanks shelled out huge amounts of cash for free agents that did not pan out.  Pavano chose to come to New York for a 4-year, $38 million contract.  What that equated to was $1.5 million for each of the 26 starts he made over that span, resulting in a perfectly mediocre 9-8 record.  The most frustrating thing about Pavano was his penchant for injuries and his seeming lack of interest in pitching for the Yanks.  During spring training in 2007 Mike Mussina said of Pavano’s various mystifying injuries, “It didn’t look good from a player’s and teammate’s standpoint.  Was everything just coincidence?  Over and over again?  I don’t know.”  After starting 17 games in 2005, resulting in a 4-6 record, he started just 9 games over his final 3 seasons in pinstripes, earning him the nickname “American Idle.”

#4 | Urban Shocker | 2/22/1918

In the first of many times the Yanks would trade for a player past his prime, they let go of Shocker, Les Nunamaker, Fritz Maisel, Nick Cullop, and Joe Gedeon to the St. Louis Browns for Eddie Plank, Del Pratt, and $15,000.  Plank and his 326 wins would eventually enter the Hall of Fame, but when he arrived in the Bronx he was 42-years-old.  It smacks of Kevin Brown and Randy Johnson doesn’t it?  Plank would retire after the 1917 season before ever pitching a single game for New York.  Shocker on the other hand would win 126 games for the Browns, including 4 consecutive 20-win seasons.  He returned to New York in 1925, and won 19 and 18 games, respectively, in 1926 and 1927, but his best years were behind him and he retired after the 1928 season.  Had we held on to him we may have had a pitcher good enough to get us over the World Series hump a few years earlier.

#3 | Jay Buhner | 7/21/1988

This trade bit us so bad that it was immortalized on Seinfeld 8 years later when George Costanza’s father berated Steinbrenner for making it:

What the hell did you trade Jay Buhner for?!  He had 30 home runs, over 100 RBIs last year!  He’s got a rocket for an arm… You don’t know what the hell you’re doing!

Buhner was a promising young prospect, but the Yanks wanted someone who could help them win immediately so he was sent to Seattle for Ken Phelps.  Phelps never played a full season in New York and batted .240 with 51 RBIs in 131 games.  Buhner would play 14 years for the Mariners, win a Gold Glove, belt 307 home runs and record exactly 900 more RBIs than Phelps did in New York.  He also torched the Yanks in the ’95 ALDS with a .458 average in the series.

#2 | Willie McGee | 10/21/1981

This trade is still mind-boggling 31 years later.  The Yanks were apparently so in need of a below-average pitcher, that they took a promising minor league prospect named Willie McGee and gave him to St. Louis for Bob Sykes, who was 23-26 in his career as a starter with a 4.65 ERA.  The time it would take you to read Sykes’ 3-sentence Wikipedia article would still eclipse the amount of time he spent as a Yankee.  After leaving the Cards he split time between Nashville and Columbus in the Yanks’ minor league system and never pitched in the majors again.  McGee would become a 4-time all-star, 3-time Gold Glove winner, the ’85 NL MVP for the Cards, and play in 4 Fall Classics.

#1 | Fred McGriff | 12/9/1982

With a bright young star named Don Mattingly at 1st base, there was no room for a kid named Fred McGriff.  The Yanks traded him to Toronto with Mike Morgan and Dave Collins for Dale Murray and Tom Dodd.  Murray was 3-6 in 3 seasons in New York with a 4.73 ERA while Dodd never played a game for the Yanks.  McGriff on the other hand made a compelling case for enshrinement with 493 career home runs, 5 all-star appearances, six top 10 finishes in the MVP vote, and a World Series crown with Atlanta in ’95.  During the title-less years of the late 80s and early 90s, his bat could have  been the missing link for Mattingly, Dave Winfield, and company.