The 15 Worst Signings In New York Yankees History

One could argue no team in all of sports has the history the Yankees do. They’ve won 27 World Series. 27. They have carried on their squads the likes of Babe Ruth, Mickey Mantle, Derek Jeter, Alex Rodriguez, Joe DiMaggio and Yogi Berra. For most of their history, they’ve been blessed with outlandish sums of money. A cashflow so large, losing some on a bad deal doesn’t sink them. It sucks, yes. It can cause fans to feel disrupted. Fissure chemistry. But unlike a smaller organization, the Yankees can overcome it. Usually.

There have been the rare occasions when the deal even stung the Yankees. When, despite their magnitude, a contract was so bad, it led to long droughts without a World Series. Coaches were fired. Veteran stars faded. Their polished legacy was lost because of failure after failure.

Because you see, there is nothing more polarizing than playing for the Yankees. Nothing. Not only are you under the microscope by the largest, most ravenous fanbase in all of sports, you’re fed to the wolves of sport critics and media, cast across every newspaper. The history can be too much for some players to bear. A weight of a thousand ghosts. Mixed with the cocktail of an unwelcome limelight, and combustion can happen. And the city of New York loves a story. Even if the story follows failure.

It’s sad, I know. But blame the addiction to a rise-and-fall story, on Hollywood, a society strung out on being entertained. Society knowing their lives aren’t as bad as the one that went up in flames.

Here are the 15 Worst Signings in New York Yankees History.


15 Kevin Youkilis: 1-Year, $13 Million

AP Photo/Matt Slocum

From 2004 to 2012, Youkilis was one of the better third basemen in the game. Yes, he battled nagging nicks and strains. But even with those, he managed to play over 100 games in seven seasons. Over that span, “Youk” hit .284, attended three All-Star games and finished top four in MVP voting twice. Though his was peak short, it was good. From 2006 to 2008, he hit .307, .312 and .304, while averaging 24 home runs a season, and playing impeccable defense.

When the Yanks gave him a boat load of cash for a year of his services in 2013, they thought they’d be getting an All-Star veteran with enough juice left to contribute. What they got was the opposite: an out of shape old man who hit .219 in 28 games played.

14 Don Gullett: 6-Years, $2 Million


When Don Gullett signed with the Yankees in 1977, he was one of the great young arms in the game. His $2 million deal, at the time, was big money. He had led the Reds to two World Series titles, and in his short seven years in the league, boasted a dominate, 91-44 record with a 3.03 earned run average.

His first year with the Yankees was by all bars and measures a success. He finished 14-4, second on the team in wins. But then the bottom fell out. He was hampered by a shoulder problem so badly in 1978, the team shut him down mid-May. That year he finished 4-2, and would never pitch another game in the pros. Needless to say, they didn't get their money's worth.

13 Kei Igawa: 5-Years, $20 Million


Igawa was the lesser known Japanese prospect, but was hotly pursued by multiple teams the same winter of 2006. Unlike Dice-K though, Igawa never had any success. From day one, he languished with the Yankees, getting knocked around by opposing teams. His rookie year, he posted a stat line of 2-3 with a 6.25 earned run average. Because of his abysmal performance, the Yankees demoted him to their minor leagues, where he played out the rest of his lucrative deal.

While four million a year doesn’t sound like a horrendous loss to a mega organization, like the Yankees, consider this: Not only did they pay the full $20 million to Igawa, but an additional $26 million for just his bidding rights. Make that $46 million over four years, for a man who won them two games. Now you get my point.

12 Jaret Wright: 3-Years, $21-Million


Wright was gifted. He had a stead of dose of heat coupled with some nasty movement. He won 20 games from 1997 to 1998 with the Indians, and looked to be a rising star. But like so many young arms, chronic problems with his shoulder, elbow and knees, created a pitcher with little to no velocity, and a once promising career disintegrated. In 2002, his earned run average ballooned to 15.71.

In classic Yankees fashion, the team signed him to a 3-year deal the winter of 2004. He was coming off his best year as a pro, with 15 wins with the Braves and sub-four earned run average. But like any of us could have anticipated, his body couldn’t hold up. Over two years he won 16 games with a mid-five earned run average.

11 Rawly Eastwick: 5-Years, $1.1 Million

Eastwick’s first four years with the Reds were filthy. He was the best middle reliever in the earlier part of the 70s, boasting a 2.40 earned run average and 57 saves as the team’s backup closer.

At the time, a deal over one million was big money for a relief pitcher. Eastwick deserved it. And yet, he’s the funniest story on this list. When he arrived at Spring Training in the spring of 1978, team manager Billy Martin decided he wasn’t worth the time. No explanation, no reason. Just a general dislike for the most dominant middle reliever in the game.

It’s so preposterous, how things ended up. Eastwick rarely found time, appearing in eight games. On July 14th, he was dealt to the Phillies for a couple nobodies.

10 Mel Hall: 4-Years, $4 Million

Lonnie Major/Allsport

Look: Mel Hall wasn’t bad. In fact, his last four years in baseball, all with the Yankees, were solid, like the rest of his career.

In fact, Mel Hall, though not an All-Star, was known for tremendous consistency. A sure glove in left field and a left-handed bat difficult to strikeout. He had above average pop, and an ability to spray pitches all over the field.

So why this list? Hall was known for his goofy aloofness. An attitude that caused friction with him and serious workhorse, Don Mattingly. You probably know Hall’s many grievances by now. But let’s keep this focused on strictly the sport.

In 1991, the team was picked for finish close to the top in the division. But chronic complaints about Hall’s drive drove wedges between players, bankrupting their chance at making the playoffs.

9 Kenny Rogers: 4-Years, $19.5 Million


Kenny Rogers, not to be confused for the corny crooner, was a sparky left handed hurler with a mean streak and a flair for big game moments. He enjoyed a tremendous borderline hall of fame career, one that saw him win over 200 games, attend four All-Star games and win four Gold Glove Awards.

The year before signing with the Yankees, Rogers posted a 17-7 record with the Rangers, a team he spent most of his 19-year career with. That year he attended an All-Star game and finished top 10 in Cy Young voting.

Unfortunately, the Yankees may have gotten the worst version of Rogers. Over two years with the club, Rogers finished 18-15 with a plus five earned run average. He had constant run-ins with then manager, the great Jim Torre, and at one point in 1997 was demoted to a middle relief role. That winter, the Yankees traded him for beans to the A’s.


8 A.J. Burnett: 5-Years, $82.5 Million


A.J Burnett was for a long time, one of the workhorse righties with an ability to eat up innings. He did so at a consistent clip, limiting the long ball with his power arm.

In 2008, Burnett won 18 games for the Blue Jays, leading the league in games started and innings pitched. But what followed this campaign were three horrendous years, years that’d cost the Yankees money, even when he was gone.

Burnett’s contract haunted the Yankees franchise. Over three seasons with the club he posted a 34-35 record with a 4.79 earned run average. Not bad, really. But not $80 million good. Especially when you consider only one of those seasons, was productive.

The Yankees were able unload Burnett with the Pirates, where he’d go on to have three of his best years of his career. But at a bargain, as the Yankees paid 70% of his salary the first two years there.

7 Pascual Perez: 3-Years, $5.7 Million


Perez was an odd duck. Zany might be the word. The 6’2” string bean, had a nasty arsenal of four pitches. His nickname was “Orbit.” It was derived from one of his many oddities, when it was rumored he was late to a start with the Braves in 1984, because he had just gotten his license and couldn’t figure out how to get to Braves stadium. So, he just circled and circled I-185, until a team official tracked him down on the freeway with a sign, “Follow me.”

Pascual was hot-and-cold, hit-and-miss. He battled drug addiction, stealing much of his prime. From 1983 to 1984 – his best – he won 29 games with the Braves, attending one All-Star game. Then followed up that campaign with a record of 1-13 and a plus-six earned run average.

Why the Yankees gave him the money is interesting. He’d won double digit games just once over a six-year span, and missed all of 1986 on suspension for drugs. Well, the Yankees gave him the money, and the rest is history. Perez won just three games over the course of the deal, and missed all of 1992 on another drug suspension.

6 Jose Contreras: 4-Years, $32 Million


The Yankees “Evil Empire,” nickname, began after the Contreras signing. At this point in the early 2000s, they were outbidding everyone. In hopes of striking it big again, after the success of fan favorite, and Cuban born, Orlando Hernandez, aka “El Duque,” the Yankees went out and made it happen with Contreras, a 31-year-old strong righty with a dominate mix of speeds and imposing personality on the mound.

You really couldn’t blame the Yankees. Contreras had wowed MLB executives for a long time. But the hype never panned. As Contreras played just 1 ½ seasons with the Yankees, battling shoulder inflammation and struggling to find a footing in their already stacked rotation. The team would deal him to the White Sox, the summer of 2004, though they forked half his salary for the remainder of the deal.

Over 1 ½ seasons, Contreras finished 15-7 with a 4.64 earned run average.

5 Spike Owen: 3-Years, $7 Million


When Spike Owen signed with the Yankees the Winter of 1992, the team thought they’d shored up their need for a consistent starting short stop. In fact, at that time, the league struggled finding good shortstops. In a couple short years, the boom would begin with names like Alex Rodriguez, Derek Jeter, Nomar Garciaparra and Miguel Tejada. But then, it was slim pickings.

Owen was coming off a career year with the Expos. He won a gold glove, hit .269 and racked up 24 extra base hits. Little did he know, the team’s future 20-year captain was around the corner, a guy, in Jeter, who’d become one of the greatest Yankees of all-time.

But back to Owen.

His career spiked. As in spiked, like stick in the ground. His one year with the club was so bad, they dealt him to the Angels to play out the remainder of the deal. His .234 average and sub .300-OBP, not something the Yankees had hoped for.

4 Carl Pavano: 4-Years, $40 Million

AP Photo/Nick Wass

Over nine years, Pavano did absolutely nothing with the Montreal Expos and Florida Marlins. The winter the Yankees signed him, he’d put up a fluke season with Florida, winning 18 games and posting a 3.00 earned run average. That season, the fluke year, he went to an All-Star game and finished sixth in Cy Young voting.

But why all the money to a guy who did nothing the eight years prior? I’ll never get it. The Yankees at the time were into outlandish spending, so they threw money at him the winter of 2004, and told him to win them some games. That…he never did.

Over three years with the Yankees, he won nine games and posted a borderline six earned run average. The Yankees dealt him to Cleveland the last year of his contract, but even then, had to pay most of his remaining salary. That’s a price tag of over four million, per win. Ouch.

3 Ed Whitson: 5-Years, $4.5 Million


Nobody could do worse than Pavano or Igawa, right? Insert, Ed Whitson, the 1980s version of Carl Pavano, except even worse, as he had been a good pitcher for most of his career.

Over his first nine years in the league, Whitson became known as a legit middle rotation guy. He racked up 60-wins, a number not incredibly strong, except that for five of those years, he was a middle relief pitcher. His highlights during that span include an All-Star appearance in 1980 and a career best 14-wins in 1984 with the Padres.

The thing that makes Whitson so annoying, is this: Though he was good, he was no ace. And despite not being an ace, he wanted near-ace dollars. So, when George Steinbrenner offered him a three-year deal the winter of 1984, Whitson countered. He got two more years plus an option for another, a slight tick in cost per year and a trove of other perks.

What followed? Fifteen wins and a 5.38 earned run average over two years with the team. They dealt him back to the Padres in 1986, where they’d fork 90% of his contract the remainder of the deal.

2 Jason Giambi: 7-Years, $120 Million

REUTERS/Ray Stubblebine

Jason Giambi had a nice career. He won an MVP, attended five All-Star Games and won three Silver Sluggers. From 1995-2001 with the A’s, the brute of a First Baseman, hit .308, and mashed 35 home runs per season.

Here’s the thing about Giambi. He admittedly took steroids. And while I’m not the most anti-steroid guy, as steroids don’t teach hand/eye coordination, but rather add longevity and turn some doubles into home runs, I do acknowledge the reality that sometimes a sudden drop off is because of the reasons above.

Giambi clearly had this issue.

Over seven years with the club, Giambi was good. Just not MVP good. During that span he hit .260, averaged 29 home runs per season, and became a liability defensively.

1 Jacoby Ellsbury: 7-Years, $153 Million

Charles LeClaire-USA TODAY Sports

When the Yankees signed Ellsbury to a gargantuan $153-million deal, I laughed. Look, Ellsbury was good with the Red Sox. But not that good. His best years came early in his career. In 2011, the speedy outfielder hit .321 with 32 home runs and 39 stolen bases. Two problems arose with Ellsbury early in his career: injury issues, and a drastic dip in stolen bases. Without the stolen base, he was slowly descending into an above average bat with no pop. So, what. You know how many outfielders fit that bill?

In three years with the Yankees, Ellsbury hit .259 with a combined 33 home runs. He’s stolen an average of 26 bases a year, his WAR declining to sub-three. So, bad, the team has flirted with him this season in the lower half of the lineup. Doesn’t sound like a $153-million man.


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