15 worst New York Yankees free agent signings in franchise history

Yankees fans have high expectations. Yankees fans don't tolerate players who disrespect their history. Yankees fans seethe when their rivals succeed. But, most of all, Yankees fans are gluttons for punishment.

Admit it. That's why you dig around in threads of Red Sox and Astros fans, hoping to land the perfect insult that finally forces them to show a shred of dignity (you won't find it). That's why you cling to players like Josh Donaldson and Aaron Hicks, sore spots you'd rather ignore, just so you can brag righteously when they come up short yet again.

And that's why you gleefully click lists of the team's worst free agent signings rather than respond to lists of the team's best moves. It's only natural.

Knock on all the wood in the world, but there hasn't been too much movement on this list of horrific decisions over the past few years. The Yankees have mostly shopped at the absolute top of the market or the absolute bottom, and have typically been rewarded.

Still, this franchise's not-so-distant past is littered with awful decisions in free agency, attempted splashes, and -- most of all -- great players who left better situations to come to New York and be overwhelmed. Truly, this experience isn't for everyone.

Also ... doesn't it seem like free agent signings are more likely to turn out poorly than they are to turn out well? A list of the Yankees' best free agent signings of all time would be littered with hyper-cheap deals, uncovered gems and pedigreed veterans fighting for one last title. A list of the worst ones? It's, uh, a lot of players they spent big gobs of money on. So it goes.

For better or worse, here's the punishment you were searching for.

Yankees Worst Free Agent Signings in Franchise History: Who's No. 1 on This List of Disasters?

Honorable Mentions:

AJ Burnett's Five-Year, $82.5 Million Deal, 2008-09: Burnett was awful in 2010 and 2011. Like, truly, franchise-history-making-ly awful. He posted the Yankees' highest ERA in a full season ever in 2011 (5.26 ERA, 1.51 WHIP). That said, he was the No. 2 starter on a World Series winner in 2009, something I personally would pay $82.5 million in just one year for. Bad contract, doesn't belong above the honorable mentions.

Randy Winn, 2010: Winn replaced Johnny Damon for only a $1.1 million base salary after the 2009 season, and while that's obviously not a large sum for the 2002 All-Star, it's still hilarious how little he did here. 29 games, 71 plate appearances, .213 average, a single homer ... and a .250 average in 87 games for the Cardinals after being DFA'd.

Kyle Farnsworth's Three-Year, $17 Million Deal, 2005-06: Farnsworth was a harrowing solution to a patchwork bullpen, but at least he pulled it together by the 2008 trade deadline, heading to Detroit in exchange for Ivan "Pudge" Rodriguez. Also, Farnsworth is a professional body builder now, and I would like to stay alive, so I'm giving him the "honorable" stamp.

Aroldis Chapman, Five Years, $86 Million, 2016 (and Three-Year, $48 Million Post-Opt-Out in 2019, Specifically): Don't do it the first time. For SURE don't do it the second time.

15. Don Gullett, Nov. 1976

One of the earliest examples in a long line of 'em of the Yankees attempting to join their rivals rather than beat them, New York dipped their toes in the free agency waters by signing Don Gullett after the 1976 season, a year capped by a World Series thumping at the hands of the Big Red Machine.

Gullett was supposed to be a big-time turncoat who would help the Yankees get over the hump created by the Reds, but a funny thing happened on the way to the end of this contract.

Cincinnati's mystique began to dissolve due to free agency; they finished second, second, first (lost the NLCS to Pittsburgh), and third the next four years. The Yankees thrived in 1977 and 1978, amid plenty of turmoil, and Gullett pitched well enough in '77, despite ending up in a neck brace for a bit after falling on the mound. He went 14-4 with a 3.58 ERA and league-leading winning percentage.

Unfortunately, he allowed 13 earned runs in 14.2 innings across three playoff starts, and his career came to an end the very next season due to painful shoulder problems. He was here for a good time, not a long time, but it would be disingenuous to say that this move "worked out" thanks to the World Series win.

14. Pedro Feliciano: Two Years, $8 Million, 2011 Offseason

Pedro Feliciano's story has an exceedingly sad ending, so we won't dwell on his Yankees career or get vitriolic; after being diagnosed with a heart condition in 2013, the ex-Mets reliever passed away in 2021.

Still, this deal must be included on any list simply because of what the Yankees received for their money: nothing.

Feliciano signed with the Yankees after a successful 2010 season with the Mets, where the sidewinding left-hander posted a 3.30 ERA and led the league in games pitched with 92, his third straight year of leading in that category.

That made it exceptionally ironic when he went on to appear in a grand total of ... zero games with the Yankees in two years, diagnosed with a torn anterior capsule and rotator cuff, due in large part to the Mets riding him so hard during his time in Flushing.

Feliciano tried to come back in 2012, but never did. Fittingly, he finished his career with a 3.97 ERA in 25 games for the 2013 Mets. Some franchises have all the fun (with Pedro Feliciano specifically).

13. Brian McCann: Five Years, $85 Million, Only Three Years Completed, 2013-14 Offseason

McCann appears on this list over Burnett because of what he failed to deliver: postseason success of any kind. Forget about World Series glory. McCann, a member of the four-man spending class of 2013-14, played one postseason game in his Yankees career, regressing annually along the way.

He also served as the commissioner of the No Fun Fantasy League, presumably doling out points for referees making the right call and cops diligently patrolling security.

After establishing himself hands down as the greatest catcher in the National League from 2006-2013, making seven All-Star teams in eight years, McCann was immediately ... drumroll, please ... not that guy anymore as soon as the Yankees paid him!

He hit 23, 26 and 20 homers during his age-30-through-32 seasons in pinstripes (fine), playing like a 36-year-old every step of the way (bad). His batting averages in the Bronx were .232, .232, and .242, and his OPS+ marks were 94, 105 and 99. The Yankees paid for a dogged captain-type with an electric bat and received Matt Nokes.

Importantly, he was traded to the Houston Astros prior to Year 4 of his deal, stole signs, and essentially eliminated the Yankees with a two-out, two-run double to put the 'Stros up 4-0 in Game 7 of the ALCS. He also, crucially, called for those 24 straight f****n' Lance McCullers curveballs. No freaking thank you to Brian McCann.

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12. JA Happ: Two Years, $34 Million, 2018-19 Offseason

The Yankees don't like letting players they've traded for at the previous deadline walk during the next free agency cycle, even if all it took to acquire them was a Brandon Drury (mid-blindness) and Billy McKinney package.

In fact, when 2018 ended, the Yankees had played the JA Happ thing perfectly -- except for the part where his hands trembled on the mound at Fenway Park for Game 1 of the ALDS.

Alas, they tied up their payroll with two additional years and $34 million of Happ money for 2019 and 2020. Having Happ's money on the books more than likely prevented the Yanks from doing anything around the Gerrit Cole signing to make the team better, a frustrating bugaboo even in hindsight knowing that the 2020 season was mostly wiped away.

And, though it's not a binary, Brian Cashman decided, "$17 million for Happ? Yes! $25 million for Bryce Harper? No way!" before watching Happ go 12-8 with a 4.91 ERA in 2019, firmly teetering on Burnett territory.

11. Tony Womack: Two Years, $4 Million, 2004-05 Offseason

Tony Womack: Extremely frustrating with the Arizona Diamondbacks! Extremely good with the 2004 St. Louis Cardinals! Extremely disappointing with the 2005 Yankees! Over, and over, and over again, so it goes.

Coming off a resurgent campaign for the '04 Cards -- the team that lost the World Series to the Red Sox and deserves eternal scorn -- Womack inked a two-year, $4 million deal with the Yankees to help stem the losing tide resulting from the 2004 ALCS. He joined such luminaties as Jaret Wright and Carl Pavano in that free agent class.

That should work!

Unfortunately, Womack -- who hit .307 with 26 stolen bases for the Cards -- could barely hit his weight in New York, parlaying his exceptional speed into a .249 average and .276 OBP. Bunt! All the time! You'll probably hit .280!

He stole 27 bases in 108 games somehow (Joe Torre condoned that?), but posted a 50 OPS+ one year after earning a 91 mark. Never an offensive dynamo, this was still somehow his very bleakest year.

Brian Cashman: Stop! Signing! Rivals! And Pretending They're Gonna Be Stars!

10. Kevin Youkilis: One Year, $12 Million, 2012-13 Offseason

Mom? Can you come in here? Cashman did it again!

Signing Youkilis to be a thorn in Boston's side didn't seem like the worst idea. He'd run aground in Beantown after an incredible stretch from 2006-2011 and found himself dealt to Chicago after 42 tepid games in 2012. Once in pale hose, he proceeded to hit .236 with a .346 OBP and 108 OPS+ in 80 games. Not bad!

Unfortunately, on a hefty one-year contract in New York, his back issues finally became too much to bear. The bare-faced ex-Sox hit .219 with a pair of homers in 28 games, the final 28 contests of his storied career.

He now runs a brewery in California called Loma Brewing Co., which is presumably where Aaron Boone drowned his sorrows after showing the Yankees 2004 ALCS clips between Games 3 and 4 against the Astros.

8. Andy Hawkins: Three Years, $3.6 Million, 1988

Whenever the Yankees massively outbid the competition (even by 1980s free agency standards) to secure their chosen target, it typically doesn't go well.

Fingers crossed for the back end of the Gerrit Cole deal.

Back in 1988, the Yanks placed undue pressure on Hawkins, a former San Diego Padres standout, outbidding the field by $1.6 million to secure the right-hander. Manager Dallas Green called Hawkins the rotation's "anchor" before the season began -- which made sense, ultimately, because he dragged the whole operation down.

Hawkins went 15-15 in 1989 for a bleak Yankee team, but posted a 4.80 ERA and led the American League with 111 earned runs allowed. The next season, he flatlined, posting an 8.56 ERA through early May, which earned him his release ... a decision the team backtracked on when a fellow starting pitcher came up lame later than evening. Hawkins' second chance at life in the Bronx ended up allowing him to throw a no-hitter and lose -- and not by a 1-0 score, either. This fellow lost a no-no 4-0, thanks to a fleet of errors behind him and five walks.

A memorable legacy. A bad signing.

7. Jaret Wright: Three Years, $21 Million, 2004

Even though he only finishes seventh here, Jaret Wright deserves a special designation. There was no discernible reason for his meltdown in pinstripes, though it certainly happened anyway. He was an ex-Yankee killer, which made the regression all the more painful. He made sense at the time, though his tenure ended up arguably worse than the other high-dollar free agent pitcher New York imported that offseason.

All in all, the surly Wright was a massive bummer, and yet another in a long line of arms the Yankees paid based on personal history and one good year.

As a hard-throwing rookie with Cleveland, Wright displayed poise on the mound in the Bronx, defeating Andy Pettitte at Yankee Stadium in Game 2 of the 1997 ALDS with six solid innings. He also beat Pettitte at home in Game 5, bringing a bit of mystique and Bomber nerves to the 1998 ALCS, where New York found their record-setting team on the brink.

That year, Wright collapsed under the pressure, allowing six earned runs in 6.2 innings. Vastly preferable.

Coming off a 2004 season that ended in disaster, the Yankees looked to reload significantly, and set their sights on Wright, who'd just gone 15-8 in 186.1 innings (3.28 ERA) for the Atlanta Braves at the age of 28.

Unfortunately, once he got to the Bronx, he looked a lot more like the version of himself who'd posted a 15.71 ERA in eight games for Cleveland back in 2002. 6.08 ERA in 63.2 innings his first year in New York. 4.49 ERA in 140.1 innings his next season, with a shoulder barking. In Baltimore for the third year of his Yankees contract. Like clockwork.

6. Jose Contreras: Four Years, $32 Million, 2002

Jose Contreras was the second-to-last great example of a bygone era of baseball, where the Boston Red Sox tried their darndest to steal targets away from the Yankees, only to be left holding an exploding banana cream pie instead.

The Yankees somehow added Contreras, a Cuban defector, after the 2002 season when he had previously been in Boston's clutches. They did the same with A-Rod the next winter. Then, the world imploded upon itself.

Contreras was actually quite good in his first season in the Bronx, especially as a starter. He dealt with shoulder issues, but went 6-1 with a 2.34 ERA as a starting pitcher during his rookie season.

Unfortunately, the postseason did not go well; seven earned runs and seven walks allowed in 11 innings across eight outings/two series. That should've been expected, though, considering he went 1–1 with a 7.43 ERA out of the 'pen during the regular season.

Ultimately, the injury issues returned during his sophomore season, and Contreras was dealt to the White Sox midseason ... where he won a World Series as part of a super-rotation of strange names (Jon Garland? Freddy Garcia?) and made an All-Star team. Acceptable career. Brutal Yankee. Sox win this round -- Sox of both colors.

5. Kenny Rogers: Four Years, $19.5 Million, 1995

Kenny Rogers was the original Joey Gallo, and The Gambler certainly gambled away his role as the highest-paid member of the Yankees' staff very quickly.

Despite concerns, at the time, that Rogers wasn't a fit in New York, George Steinbrenner presented the counterargument, "Na na na NA NA, I CAN'T HEAR YOU!" He signed Rogers to a nearly $20 million deal the same offseason he added Cone, and by Year 2, he was looking for any way possible to wriggle out of it.

Rogers was a perfectly competent starter (competent-to-good!) everywhere else he ever resided throughout his career, eventually dominating the Yankees in the 2006 ALDS with the Tigers as a 41-year-old man (aided by a handful of goop). That places him in the worst category of failed Yankees free agent signings: arrives, sucks, gets aggrieved about something, takes his own sucking out on the organization at a later date. What are you so mad about? You were the one who sucked!

The Yankees won the 1996 World Series, but no thanks to Rogers, who posted a 9.00 ERA in two innings in the ALDS, 12.00 ERA in three innings in the ALCS, and 22.50 ERA in two innings in the World Series. They basically took him out of the mix, and he still managed to unwrap all the Christmas presents early and poop in the sink.

By summer 1997, the Yankees were eating chunks of Rogers' contract to send him to Oakland. It was that day that he vowed revenge for ... getting him out of a bad situation? Whatever. Dudes, am I right?

4. Kei Igawa: Five Years, $20 Million (Plus $26 Million Posting Fee), 2006

Kei Igawa was supposed to be a perfectly capable No. 4 starter in the Yankees' rotation in 2007 after coming over from the Hanshin Tigers. Commonly-accepted wisdom indicated he was down from his peak years overseas, but still had something to contribute.

Commonly-accepted wisdom was extremely wrong.

Igawa totaled 71.2 innings in the bigs over two years with an unsightly 6.66 ERA, an accurately devilish reminder of the money the team set on fire to bring him in. During the final years of his deal, Igawa was mired in Scranton/Wilkes-Barre, which probably felt better anyway. He could still pitch. But none of it mattered. Countryside. Ideal.

Those numbers don't even accurately reflect how horrific Igawa's career in pinstripes was. 67.2 innings of that 71.2 total came during his rookie year in 2006. He allowed 15 bombs during that limited duty, posting a 6.25 ERA/6.37 FIP. He walked 37 men, good for a 1.67 WHIP.

Good news? The next season, his FIP was just 3.13! Bad news? His WHIP almost matched (3.25), he only contributed four innings, he surrendered 13 hits and six runs, he didn't whiff a single batter, and he never pitched in MLB again.

Anyway, here's a hilarious chunk from Joe Torre's The Yankee Years about Igawa's first bullpen session in America:

Then-bullpen catcher Mike Borzello was assigned to catch Igawa’s first bullpen session in camp and was very underwhelmed. 'He threw three strikes the whole time. His changeup goes about 40 feet. His slider is not a big league pitch. His command was terrible,' said Borzello. 'I hope he’s hurt, so there’s an explanation for throwing like that.' Definitely not an encouraging set of words from someone who’s caught a lot of pitchers.

Is that good?

3. Ed Whitson: Five Years, $4.4 Million, 1984

If Kenny Rogers was the evolutionary version of "Crafty, Angry Guy Who Vowed Revenge on the Yankees Organization After Taking Their Money," Whitson was the Charmander.

He did it first, but he also probably did it better than any of the angered chumps who followed in his footsteps.

Whitson joined Yogi Berra's Yankees for the 1985 season, coming off a solid showing in San Diego, Andy Hawkins-style. Unfortunately for Whitson, Berra was replaced early in the season by (shocker) Billy Martin, and he went from a 3.24 ERA in '84 to a 4.80 mark in '85, even though his salary had been raised to triple the league average.

Oh, right, and he and Billy Martin got in a fistfight in the middle of the season, where he shattered Martin's arm while Martin busted his rib. Right.

The next year, with Martin gone, Whitson was way worse, holding onto a 7.54 ERA in the Bronx before the Yankees bailed and dumped the next 3.5 years of his contract back onto the Padres' plate. Hard to succeed if you actively hate everyone you're trying to succeed for.

Stop me if you've heard this one, but Whitson had the best years of his career in San Diego after the trade, posting a 2.66 ERA in 227 innings while the Yankees paid his salary. Would be fantastic if this stopped happening someday. Would be just electric if this stopped happening. Makes you want to crack your own rib in half.

2. Carl Pavano: Four Years, $39.95 Million, 2004

For years, Pavano has held the top spot on any of these "worst contract" retrospectives. It took a God among Sucky Men to toss him down to No. 2, but we'd argue it'd be impossible to snub our No. 1.

Pavano's story has been told repeatedly, with other names attached, in the preceding pages. Best year of his life (2004, 18-8, 3.00 ERA, 222.1 innings). Red Sox wanted him. Yankees in desperation mode. Brian Cashman unable to identify starting pitching targets to save his life. Moderate overpay. Disaster.

Yet, somehow, Pavano ended up as the one who craved revenge, raising his game in 2009 and 2010 as a Minnesota Twin whenever the Yankees came to town. Baffling the mental pretzel these struggling pitchers turn themselves into in their repeated attempts to play the victim.

Pavano started off alright with the Yankees (3.10 ERA in March/April, lots of hits allowed), but came down with a bum shoulder and finished the year 4-6 with a 4.77 ERA in 17 starts. He was good on the road! 3-3, 2.89 ERA in eight starts. He was horrible at home! 1-3, 6.89 ERA in nine starts. How. Do. We. Keep. Targeting. These. People?!

Add in the injuries and a series of remarkable lies -- Pavano hid a car wreck from the Yankees in 2006, which resulted in two broken ribs (hard to hide, with the clear rib pain!) -- and you have an unmitigated disaster.

Luckily, although Pavano fared well for the Twinkies against the Yanks, Jorge Posada and A-Rod got him late in Game 3 of the 2009 ALDS to clinch an ALCS berth, and six innings, 10 hits and four earned runs later, he also lost Game 2 in 2010. Damn. That'll chap your behind, an injury Pavano also suffered during his years in the Bronx.

1. Jacoby Ellsbury: Seven Years, $153 Million, 2013

The GOAT. The absolute, undisputed worst free agent addition in Yankees history (so far), a contract that turned so bleak the Yankees turned to the long arm of the law to resolve it.

In Boston, Ellsbury was a thorn in the Yankees' side and a star of the Red Sox 2007 and 2013 playoff runs, but he wasn't exactly a stable threat. He had a full season lost to injury in 2010 after he collided with a fellow outfielder, and lost a half-year during the Bobby V-helmed campaign in 2012 (but didn't we all?).

Even before he became a Yankee, there was an air of mystery attached to his name -- has anyone figured out why on earth he hit 32 home runs during an MVP-caliber 2011 season, then only topped 10 once during the rest of his career? His full seasons to start his career consisted of 9 bombs, 8 bombs, and a hefty 32, then back down to 9. Would love an earnest explanation.

Everyone agreed Ellsbury was an overpay at the time, but hell, the Yankees could clearly afford it based on the rest of their offseason (McCann, Carlos Beltrán, eventually Masahiro Tanaka). Plus, didn't it feel good to steal from the Red Sox? Ells would steal some bags and hit .270 at worst, though he might go into the void from time to time after bonking heads with a fellow outfield mate.

His first season in the Bronx was on point: those 16 dingers, 39 stolen bases, 111 OPS+. Would've mattered more on a better team. But he never again was a league-average offensive player, peaking at a 97 OPS+ in 2017, his fourth (and final) active year with the Yanks.

From there, he missed two full seasons with oblique issues, back issues, hip problems (and eventual surgery), and foot stuff, then was taken to court in an attempt to void the end of his deal because of a visit to an unapproved doctor. No word on whether it was Dr. Pavano or Rogers.

Eventually, Ellsbury got his money, but that's how petty the Yankees were towards the end of this deal. It's hard to imagine anything souring harder -- and we'd rather not imagine it anyway.