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For the post-Christmas blues: The Yankees' 10 worst free agent signings of all-time

The Yankees really should have held onto the gift receipts for these players.

Why yes, Carl, your Yankees tenure was like that.
Why yes, Carl, your Yankees tenure was like that.
The Star-Ledger-USA TODAY Sports

Have you ever had a present that you couldn't wait to use once you opened it? I know I do. Back in the day, I really wanted "Hey You, Pikachu" for the N64 because I was ridiculously into Pokemon and the exact kind of sucker Nintendo hoped to find with this game. Almost as soon as I played it and realized how worthless it was aside from yelling obscenities or "PlayStation" at Pikachu, I instantly regretted putting it near the top of my Christmas list. Sorry, mom.

Useless personal anecdotes about my weird childhood aside, the Yankees have sure had their share of buyer's remorse over the years with some of their free agent signings. While some free agents became gems like the top 10 free agent signings I counted down last week, the Yankees have had more than their share of stinker signings. This fact is hardly a revelation; it's the nature of the Yankees' business. Free agency is naturally an inefficient process, as most often, teams (not just the Yankees) will pay premiums for players' decline years. The investments rest on the hope that the earlier years of the contract will yield team success and the opportunity to profit off such triumphs for decades to come.

Unfortunately, that just wasn't the case with the players listed below. It didn't take long for the honeymoons to end, and the Yankees paid the price. As with the previous list, I will not be counting any re-signings, so Alex Rodriguez's 10-year contract following the 2007 campaign and CC Sabathia's post-opt-out extension from 2011 are out. (Also, Hideki Irabu was acquired via trade, not signed, so he's not here, either.) These are just players who were new to the team, like shiny toys under a tree, who turned out to be big disappointments.

Honorable Mentions

Before getting into the list, here are a few players who didn't quite make the cut, but deserve some heavy sighs:

  • Don Gullett, 6/$2M, 11/18/1976: Just the second free agent the Yankees signed, Gullett was terrific with the Reds while they repeated as champions in '75 and '76, then was solid in the regular season for the Yankees' 1977 champions. He wasn't as good in the playoffs though, and after just eight starts in '78, his career was suddenly at its end due to shoulder injuries. The Yanks were still paying him in 1982. Whoops.
  • Rawly Eastwick, 5/$1.1M, 12/9/1977: This one is a favorite of mine. The righty Eastwick was a relief ace for the Reds prior to ending up on the Yankees. However, manager Billy Martin simply didn't like him and it was hard for him to find work. Eastwick amazingly made it into just eight games before the Yankees dealt him to the Phillies on June 14th, two months into his five-year deal. It's not as though Eastwick was bad; this is just amusing in retrospect.
  • Mel Hall, 3/$3.3M, 11/30/1989: Hall wasn't that bad on the field as a Yankee. Just screw that guyNow and forever. Zero.
  • Kenny Rogers, 4/$19.5M, 12/30/1995
  • Jaret Wright, 3/$21M, 12/28/2004: Both Rogers and Wright are kind of in the same category, though Rogers came to the Yankees with more of a recent track record with the Rangers. (Wright's '04 season with the Braves was his first healthy campaign as a starter in five years.) Both were inked to multi-year contracts for a nice chunk of change, and both performed mediocre at best, miserable at worst. Rogers had a 5.11 ERA (93 ERA+) over two years before getting dealt to the A's for a player to be named later (thanks for Scott Brosius, Billy Beane!), and Wright pitched to a 4.99 ERA (89 ERA+) over two seasons, then likewise got traded. Count these as missteps from Bob Watson and Brian Cashman, respectively.
  • Reliever Lightning Round!: In the first decade of the 2000s, Cashman and company were desperate to find relievers who could bridge the gap to Mariano Rivera the way Mike Stanton, Jeff Nelson, and Ramiro Mendoza did during the dynasty years. Tom Gordon panned out, but all of Steve Karsay, Paul Quantrill, Mike Myers, Kyle Farnsworth, and Pedro Feliciano were new signings whose performances ranged from "good then hurt thanks to the Joe Torre bullpen experience" (Karsay and Quantrill) or just always hurt (Feliciano). Just for good measure, the two re-signings of mid-season lefty acquisitions Felix Heredia and Damaso Marte were pretty awful as well, though at least Marte had a good postseason in '09. This series of failures prompted the Yankees to work on developing homegrown relievers more effectively. Took long enough.

Now onto the list...

10. Kevin Youkilis, 1/$12M, 12/14/2012

This contract is the only one-year deal that will be on this list. As a rule, I generally don't care about one-year deals. If they work out, awesome. If not, whatever, the player will either be gone by the end of the year or midseason at best. They don't hamstring the payroll. I will make an exception for Youk though because hell if this wasn't arguably the worst one-year contract in big league history.

I don't blame the Yankees for giving Youkilis a shot. I even advocated it because their third base situation was already going to be a disaster at the start of 2013 before all the Biogenesis crap came down because Alex Rodriguez needed hip surgery anyway. There weren't many third basemen available on the market. Thus, Youk became a Yank, and it turned into the worst-case scenario that numerous Yankees fans feared. He was healthy for a little more than two weeks before he began to suffer tightness in his back. The Yankees chose not to DL him because they thought he might recover before the DL stint would have been up, and that strategy backfired, limiting their roster flexibility and becoming pointless when he hit the DL on April 28th anyway. He briefly returned for 11 games of horrid production at the beginning of June, then had his season end due to back surgery.

For their $12 million investment, the Yankees received 28 games of .219/.305/.343 production, a mere 80 OPS+. Youk moved on to Japan in 2014, where he only played 21 games before another injury ruined his season (surprise, surprise). That was the end of his professional career. We got to experience his MLB finale! It was just another element of joy to add to the miserable 2013 season.

9. A.J. Burnett, 5/$82.5M, 12/12/2008

Like the Jason Giambi signing on the previous list, some would say that Burnett should not be on this list at all and others would say he deserves to be much higher. I tend to lean more to the crowd that doesn't think he needs to be here, but something must be said for giving a guy over $80 million to be an awful pitcher in two of three seasons, then paying to get him out of town. Flags fly forever, and I will always have a soft spot for Burnett's brilliant Game 2 performance in the 2009 World Series that tied the Fall Classic at one apiece. Had he come up small there, the Yankees would have been looking at an 0-2 deficit before even going on the road. Thankfully, he didn't, and the Yankees won that World Series.

Now due to various forms of profit and royalties from that title, the Yankees will surely recoup all of the sunk cost from the rest of Burnett's contract, but boy, it was not a fun experience. (Mark Teixeira didn't make this list because in addition to the championship, he at least put together a number of decent seasons, not just one.) Although Burnett had a similarly productive season in '09 to his healthy years in Toronto and Florida, his next two years were dreadful. He pitched to a 5.26 ERA and 1.511 WHIP while also losing his only playoff start in a below-replacement level 2010, then followed it up with another 5.15 ERA season-long slog in 2011, a year that saw him surrender 31 homers. He stayed healthy, but it was hardly worth it, especially at $16.5 million per year. Burnett at least won his final start in a must-win ALDS Game 4 thanks to some awesome defense by Curtis Granderson.

After adding Hiroki Kuroda and Michael Pineda, the Yankees had too many cooks starters in their scheduled 2012 rotation, so they finally decided to send Burnett away. Just before pitchers and catchers reported, the Yankees traded Burnett to the Pirates for two non-prospects (despite 80 grade names), and they even threw in $20 million over two years just so that he wasn't on their team. It was a move that didn't look as good when Burnett became the ace of a Bucs renaissance, but one that felt necessary. It's hard to believe that Burnett could actually replicate that form while pitching half his games at homer-happy Yankee Stadium. Ultimately, it was a bad contract, but hey, we'll always have '09 Game 2, A.J.

8. Pascual Pérez, 3/$5.7M, 11/21/1989

There have been few characters in big league history quite like Pérez, a zany guy who had an incredibly up-and-down career in the '80s. This is the same person who was nicknamed "Perimeter" for orbiting the Braves' stadium on I-285 several times in a desperate attempt to get there after obtaining his driver's license. Pérez was an All-Star caliber pitcher when he was at his best, but he also struggled with personal demons and serious substance abuse problems. Despite these red flags, new GM Harding "Pete" Peterson and owner George Steinbrenner felt comfortable with giving Pérez a three-year deal that would pay him as much as Nolan Ryan in 1990.

Perhaps not surprisingly, the deal was a disaster. Pérez made just three starts in '90 before he hit the DL with shoulder soreness, an injury that eventually led to rotator cuff surgery that kept him out of the game until May of '91. After four more starts, he missed two and a half months with inflammation in the same shoulder, then closed out the year with 10 starts of 3.70 ERA ball. Those were the last appearances Pérez would make in his MLB career. He tested positive for cocaine and was suspended for the entire '92 season, ending his three-year deal with only 17 starts in pinstripes. Likely due in part to Pérez's immediate injuries as well as an eventual last place finish, Peterson was fired before even reaching 12 months on the job. At least that led to Steinbrenner hiring scouting genius Gene "Stick" Michael as his GM.

Sadly, Pascual's life odyssey turned tragic in 2012 when he was killed in a robbery attempt in his native Dominican Republic He was 55 at the time, a charismatic man taken too soon.

7. Dave LaPoint, 3/$2.5M and Andy Hawkins, 3/$3.6M, 12/1988

It's cheating a little bit to put two players in one spot, but LaPoint and Hawkins are so alike that it would have been even more arbitrary than this list already is to list them separately. As with Pérez, both pitchers were signed with the hope of boosting the Yankees' rotation from the '80s, the part of the team that always seemed to doom them in the end despite a capable offense. The lefty LaPoint and the righty Hawkins were signed to three-year deals within days of each other by then-GM Bob Quinn during the 1988-89 off-season. LaPoint had pitched capably to a 3.35 ERA and 122 ERA+ in 52 games over his previous two seasons, and Hawkins was coming off one of the finest years of his career, one which also saw him notch a 3.35 ERA, though this one came in 33 starts and 217 2/3 innings.

Both pitchers were not even 30, and these deals weren't terribly long. Yet nothing went right for either of them. LaPoint was just awful immediately, getting knocked around to the tune of a 5.26 ERA and 1.680 WHIP over 20 starts in '89. Hawkins wasn't quite that bad, but he wasn't much better, as his 4.80 ERA and 1.507 WHIP in 34 starts could attest. A league-high 111 earned runs allowed didn't help matters for Hawkins, who followed that poor year with an even worse one in 1990. The one infamous start where he threw eight no-hit innings and lost thanks to atrocious Yankee defense was the lone highlight, if it can even be considered one; he ended the year with a 5.37 ERA and a 5.12 FIP. Although LaPoint improved from terrible to just mediocre with a 96 ERA+, it wasn't a joy to watch, either.

The Yankees lost 87 games in '89 and a league-worst 95 in '90, and neither LaPoint or Hawkins were around by the end of their contracts. LaPoint was released at the start of spring training '91 and made it into just two more MLB games before his career ended. Hawkins survived just a couple more poor months before getting released himself. Oakland picked him up, and he wasn't much better in 14 starts before once again finding himself out of work. This time, he did not make it back to a big league mound. All told, Hawkins and LaPoint gave the Yankees about -2.0 WAR for their combined $6.1 million investment. That's uh.. a minus.

6. Jose Contreras, 4/$32M, 2/6/2003

Ah, the days of Jose Contreras excitement. After their great success with former Cuban star Orlando Hernandez ("El Duque"), the Yankees tried to strike gold twice with this big righty, a 31-year-old starter whose name had been on major league executives' minds for years. Contreras was an international pitching sensation, and he had even dominated a potent Orioles lineup during a 1999 exhibition series with the Cuban national team. In a hotly-contested bidding war with the Red Sox, the Yankees won out and signed Conteras prior to the '03 campaign. The competition, likely helped by the fact that Steinbrenner essentially told his Yankees representative that he would be fired if Contreras wasn't signed, led to the Yankees getting their "Evil Empire" nickname from Red Sox president Larry Lucchino.

But for all the hype, Contreras never truly found himself in New York. Maybe part of that was the result of a confusing first season, where he spent two and a half months on the DL due to shoulder inflammation and only appeared in 18 games and nine starts since there wasn't much room in the crowded rotation. The results were good (a 134 ERA+ and 9.1 K/9), but it was in just 71 innings. Thrust into a very difficult situation when he was forced to relieve the injured David Wells in the second inning of Game 5 of the World Series having pitched two scoreless innings the day before, Contreras did not win much favor with the fans, as the Marlins scored four runs off him in three innings and took the series lead. The next year, he was finally guaranteed a rotation spot, but again, he just didn't pitch well. In 18 starts, he yielded a 5.64 ERA and a 5.83 FIP, hardly demonstrating that he was worth his high-priced contract.

Contreras's Yankees tenure came to an end when the White Sox accepted an offer of Contreras and $3 million for two-time All-Star Esteban Loaiza. It made some sense at the time, as Contreras was still struggling and though his second All-Star season in '04 had not been nearly as impressive as his '03 All-Star berth in which he led the AL with 207 strikeouts, Loaiza was still considered a capable rotation piece. An 8.50 ERA in 10 games (six starts) said "so much for that," and Contreras went on to at last put it all together in Chicago, where he played a crucial role on the 2005 team that ended an 88-year championship drought on the South Side. Naturally.

5. Dave Collins, 3/$2.47M, 12/23/1981

Unless you really dislike Danny Tartabull, Jason Giambi, or Mark Teixeira, free agent position players haven't been nearly as bad for the Yankees, though Carlos Beltran could end up on this list before long. Rondell White and Tony Womack were another few poor short-term investments, but their deals were easy to overcome. There have been a couple exceptions though; after the Yankees lost the 1981 World Series to the Dodgers, George Steinbrenner decided that the team's offense was focused on power a bit much and instead needed to develop their small ball game. Yes fans, it was the accursed #TooManyDamnHomers trend before Twitter co-founder Evan Williams was even 10 years old. Reggie Jackson's time with the Yankees came to an end, and in came, among others, former Reds speedster Dave Collins. Following a few seasons of promise with the Angels and Mariners, the 29-year-old outfielder made a name for himself in 1980, when he stole 79 bases for Cincinnati.

Even though he slipped to 26 steals in 95 games for the Reds in '81 and the Yankees didn't really have a definite position for him, Steinbrenner made sure that GM Bill Bergesch added Collins to his '82 "Bronx Burners" squad. It was bizarre from the get-go, with the Big Stein reorganizing spring training drills to focus on speed and just generally causing all sorts of idiocy. Turns out, the big plan was a failure! (But please, go on about the "if the Boss was alive" nonsense.) The Yankees' powerful pennant-winning offense from '81 slipped to mediocre in '82, and they ended the year under .500. Collins only hit .253/.315/.330 with an 80 OPS+ and -0.7 WAR in 111 games, which were confusingly split among four positions, and he stole just 13 bases in 21 attempts.

Realizing his mistake, Steinbrenner had Collins shipped out after the season, but even that trade ended brutally for the Yankees. It was a deal with the Blue Jays, and the Yankees were able to get two pitchers they wanted in return: Dale Murray and Tom Dodd. Although neither ended up doing much of anything for the Yankees, the two prospects the Yankees sent to Toronto in addition to Collins sure as hell succeeded. One was 22-year veteran pitcher Mike Morgan, and far more damaging was the loss of a man who went on to hit nearly 500 homers, a 19-year-old first baseman named Fred McGriff. Ouch. To his credit, Collins has always spoken highly of the Yankees organization, but woof, was this a bad signing.

4. Spike Owen, 3/$7M, 12/4/1992

It cannot be said enough how difficult it is going to be for some Yankees fans to deal with life at shortstop after Derek Jeter. Throughout the major leagues, shortstop is a position of instability, and prior to Jeter, it was no different for the Yankees. Prior to the Captain, the Yanks had gone through five Opening Day shortstops in five years. One of these men was Spike Owen, a 10-year veteran who was supposed to finally bring some stability to the position. The 32-year-old Owen was coming off a career year with the Expos in 1992, when he hit .269/.348/.381 with 26 extra-base hits and a 107 OPS+  in 122 games. Even his three seasons before that in Montreal had been decent for a shortstop: .240/.335/.346 with a 93 OPS+ and solid defense.

GM Stick Michael made several wise investments during the 1992-93 off-season, like signing Jimmy Key and Wade Boggs while also adding Paul O'Neill's bat via trade. He was probably due for a clunker, and boy, did he get one in Owen. During his one season in pinstripes, Owen hit a paltry .234/.294/.311 with an ugly 66 OPS+ and just 0.7 WAR. It became evident quite quickly that Owen was not going to cut it at shortstop, and with the Yankees trying to keep pace with defending champion Blue Jays in the tight AL East, Owen began to lose starts to the hotter-hitting Mike Gallego and Randy Velarde. From August onward, Owen made only 34 plate appearances and nine starts.

It was time to cut bait, and Michael dealt Owen and about $2 million to the Angels during the 1993-94 off-season. After a rebound in '94, Owen fell back to his '93 numbers when the players' strike ended in April of '95, and that was it for Owen's career. Neither Gallego or Velarde became the Yankees' long-term solution at shortstop, but man, they were better than Owen.

3. Kei Igawa, 5/$20M, 12/27/2006

Oof. This guy. If Hideki Matsui was just about the ideal Japanese player signing, Kei Igawa would have to be the worst-case scenario. Hideki Irabu was a bust, but at least he had his good stretches here and there, garnering a couple AL Pitcher of the Month awards. There was nothing that worked out for Igawa, unless you consider first place on the Triple-A Scranton team's all-time win list an accomplishment. The lefty was a steady performer for the Hanshin Tigers and even pulled off the equivalent of 2011 Justin Verlander by winning the equivalent of both his league's Cy Young and MVP awards in 2003. Igawa's game slipped a little over the next two years, but he rebounded to notch a 2.97 ERA and league-high 194 strikeouts in 2006.

The Yankees paid about $26 million to Hanshin just to negotiate with Igawa, and they got their man on a five-year, $20 million deal. If one thought the Yankees were looking past possible red flags to counter Boston's move in signing top Japanese starter Daisuke Matsuzaka, it would have been hard to disagree. The tone for Igawa's Yankees tenure was set on his first day with the team, which was recounted in Joe Torre's Yankee Years. The story's just so perfect that I'll leave it as is:

Igawa story

Great. Just outstanding. Sure enough, when Igawa began the season in the rotation, he was pounded to the tune of an eye-popping 7.84 ERA and five homers in four starts. After one brief brilliant outing in relief of the injured Jeff Karstens on April 28th against the Red Sox, he made one more start and was wrecked again. The Yankees sent him down to the minors to work on his mechanics, to no avail. When he returned in late June, he posted a 5.97 ERA and gave up 18 walks and seven homers in six starts. The Padres made a waiver claim on him, but ownership did not want Cashman to make a trade just yet. (Brilliant.) Off he went to the minors again; he made just two more appearances in a Yankee uniform that year, ended the '07 campaign with an abysmal 6.25 ERA, 6.37 FIP, and a 1.670 WHIP.

After such an awful start to his career, the Yankees had no intentions of trusting him with a spot in the '08 rotation. He reported to Triple-A Scranton, where he remained until the Yankees needed a spot start from him on May 9th against the Tigers. The result? Three innings, 11 hits, and six runs. No walks or homers though, so improvement maybe! Once again, he was banished to Scranton until another emergency, a June 27th doubleheader against the Mets. Igawa threw one scoreless inning of relief. Then, he went back to Scranton and was never heard from in New York ever again. Cashman did not mince words in his assessment of the deal, one that he initially supported: "It was a disaster. We failed." Sixteen games and a fitting 6.66 ERA? You bet.

For the duration of his five-year contract, Igawa and the Yankees maintained an increasingly awkward stalemate, as the Yankees tried to arrange a trade to Japanese teams on multiple occasions, only to have Igawa, who continued to commute from Manhattan to Scranton and Double-A Trenton, turn them down. The nice thing about the Yankees' high payroll was that they could afford to bury Igawa's $4 million salary in Triple-A and profit anyway; they won a World Series this way, so I don't consider this the worst deal in their history. Following the 2011 season, the ugly marriage finally ended, and Igawa was free. No major league team pursued him, and he return to Japan with the Orix Buffaloes. He's battled injuries, but he's certainly had better luck back there. In the Bronx though, it just wasn't meant to be.

2. Carl Pavano, 4/$39.95M, 12/20/2004

Like Contreras, let it not be said that the Yankees were alone in their free agent pursuit of the most infamous free agent of this generation. Believe it or not, multiple teams wanted to sign the former Marlins pitcher who would one day be mocked as "American Idle." The free agent tour was called "Pavanopalooza," and while multiple teams like the Red Sox and Tigers made him offers, the Yankees were the ones who signed Carl Pavano to that four-year contract.

What followed were four seasons of nigh-endless frustration. It started off so well with a 3.10 ERA during Pavano's first month as a Yankee in '05 and even a five-hit shutout in one start the next month. Then, things quickly went south. Rotator cuff tendinitis and right shoulder inflammation ended his season in late June. He did not appear on a big league mound again until Opening Day 2007. In between, his teammates questioned his desire to return to the field, he suffered a "bruised buttocks," he hid a rib cage injury sustained in a car accident until just before he would have returned in late '06, and he turned into a pariah among the fans. His long-awaited return to the mound in '07 lasted two games until a dreaded UCL tear led to Tommy John surgery because of course that had to happen, too. When he returned from that surgery in August of '08, fans were already too checked out from a season of disappointment to really care too much that he was starting. He was predictably terrible with a 5.77 ERA and 5.37 FIP in seven starts.

For just about $40 million, the Yankees received 26 starts, 0.4 WAR, a 5.00 ERA, and a ceaseless headache. When he reached the playoffs with the Twins the next two years, it was annoying that he decided to be decent again, but boy was the schadenfreude in full force as the Yankees pounded him in the ALDS both times. In the end, Pavano was just another example that bad contracts can happen to anyone. Had the Yankees not pursued him, he very well could been this disaster for the Red Sox, the Tigers... you name the team. Free agency can be a bitch.

1. Ed Whitson, 5/$4.5M, 12/27/1984

Pavano has topped similar Yankees "worst free agents" lists in recent years, but to me, one man is still the king. Just days after the 30-year anniversary of his signing, Ed Whitson remains atop the list of worst free agent signings in Yankees history. The 6'3" righty initially turned down Steinbrenner's offer before the Boss came back with a sixth year option and other perks. Instead, the eight-year veteran inked the deal with the Yankees and probably the most arduous 19 months of Whitson's career began.

Whitson had been a fine pitcher for most of his career, highlighted by a 1980 All-Star appearance with the Giants and a 3.24 ERA and 3.49 FIP in 31 starts for the NL champion Padres in '84. Although the Tigers lit him up in his only Fall Classic appearance, his eight innings of one-run ball in NLCS Game 3 against the Cubs with his team in a win-or-go-home scenario were imperative to them getting that far in the first place. No such good times came for Whitson during his first couple months on the job however; opposing batters hit .357/.398/.559 during those 11 starts, ballooning his ERA to 6.23. The boos were raining down already and Whitson seemingly had no answers. He had a nice turnaround for a month, tossing two shutouts and recording a 1.14 ERA in 47 1/3 innings over six starts, but it was all downhill after the All-Star Break.

"I will never mention that man's name again, ever." -Ed Whitson on Billy Martin

For the remainder of the season, batters found their earlier form against Whitson, again crushing him to a .341/.380/.529 triple slash in 13 starts, which yielded a 6.64 ERA. Rather than easing the pressure, manager Billy Martin only made things worse with his criticism and mistreatment of Whitson. Things came to a head in an ugly scene in Baltimore when Martin and Whitson brawled at a hotel, a fight that ended with a broken arm for Martin. It feels almost ludicrous that such calamity could actually happen, but well, there it was. Martin was fired after the season and was replaced by Lou Piniella, who tried to pitch Whitson as little as possible at home (not by request), where the fan treatment was absolutely miserable.

With a 7.54 ERA in 14 games, the Ed Whitson Era mercifully ended when he was dealt back to the Padres on July 9th. He recovered to pitch decently over five and a half more years there, but outside of San Diego, his career will always be defined by that awful year and a half in New York. To this day, he refuses to talk about Martin, saying "I will never mention that man's name again, ever." I don't blame him. Whitson continued to receive death threats on the occasions when he pitched at Shea Stadium. Stay classy, Yankees fans. Nonetheless, the entire recipe of bad pitching, well-publicized fights with the manager, and likely costing the Yanks the AL East in '85 stacks up to Whitson being the worst Yankees free agent signing of all time.