Each MLB Team's Biggest Free-Agency Fail of the Past Decade
Every MLB free-agent signing comes with some degree of risk.
The more years and dollars a team commits to a player, the more risk is involved, and sometimes a huge financial commitment can blow up in a team's face.
That's what we'll be focusing on here: those unmitigated disasters.
Ahead, we've selected each MLB team's biggest free-agency fail of the past decade, along with a few honorable mentions for each club to paint a better picture of the full field of contenders.
The parameters were simple. In order to be considered, a player had to have:
- Signed his contract no earlier than the 2008-09 offseason.
- Been officially declared a free agent prior to signing. That took in-season contract extensions out of the equation but did open the door to include players who tested the market and then re-signed with their original teams, such as the fellow pictured above.
Simple as that. Now let's get started.
Arizona Diamondbacks
1 of 30
Worst Signing: OF Yasmany Tomas
Date: December 9, 2014
Terms: Six years, $68.5 million
Impressive raw power and a strong history of production in the Cuban National Series made a then-24-year-old Yasmany Tomas a hot commodity after he defected in 2014.
He has a 31-homer season to his credit in 2016, but his lack of on-base ability (.307 OBP) and defensive shortcomings (-30 DRS) have made him a minus-2.4 WAR player in three MLB seasons.
After being outrighted off the 40-man roster before last April, he hit a lackluster .262/.280/.465 at Triple-A, before opting into the final two years and $32.5 million this winter. He'll likely play out his contract in the minors.
Other Bad Free-Agent Signings
- SP Bronson Arroyo (Feb. 7, 2014—2 years, $23.5 million)
- SP Brandon McCarthy (Dec. 11, 2012—2 years, $15.5 million)
- OF Cody Ross (Dec. 22, 2012—3 years, $26 million)
Atlanta Braves
2 of 30
Worst Signing: CF Melvin Upton Jr.
Date: November 29, 2012
Terms: Five years, $75.25 million
Melvin Upton Jr. posted a 108 OPS+ in 2012, hitting .246/.298/.454 with 28 home runs and 31 steals on his way to 2.7 WAR.
Decent production? Sure.
Worthy of a massive five-year, $75.25 million contract? Absolutely not.
He went on to hit .198/.279/.314 with minus-2.1 WAR in two seasons with the Braves before he was packaged with closer Craig Kimbrel and traded to the San Diego Padres.
Other Bad Free-Agent Signings
- SP Kenshin Kawakami (Jan. 13, 2009—3 years, $23 million)
- SP Derek Lowe (Jan. 15, 2009—4 years, $60 million)
- IF Sean Rodriguez (Nov. 30, 2016—2 years, $11.5 million)
Baltimore Orioles
3 of 30
Worst Signing: 1B Chris Davis
Date: January 21, 2016
Terms: Seven years, $161 million (re-signed)
Chris Davis had a huge offensive season in 2015, posting a 147 OPS+ while leading MLB with 47 home runs to go along with 31 doubles, 117 RBI and 100 runs scored for 5.3 WAR.
However, the Orioles seemed to be bidding against themselves on the free-agent market when they gave him a massive seven-year deal.
He posted 3.3 WAR with 38 home runs in the first year of the deal. But his production fell off dramatically the following year (minus-0.1 WAR, 26 home runs), and he turned in one of the worst seasons in MLB history in 2018.
The 32-year-old hit a brutal .168/.243/.296 for a 50 OPS+ in 522 plate appearances and had minus-2.8 WAR.
Other Bad Free-Agent Signings
- SP Alex Cobb (March 21, 2018—4 years, $57 million)
- RP Mike Gonzalez (Dec. 18, 2009—2 years, $12 million)
- RP Kevin Gregg (Jan. 13, 2011—2 years, $10 million)
- SP Yovani Gallardo (Feb. 25, 2016—2 years, $22 million)
- SP Ubaldo Jimenez (Feb. 19, 2014—4 years, $48 million)
- RP Darren O'Day (Dec. 14, 2015—4 years, $31 million) re-signed
- SP Tsuyoshi Wada (Dec. 14, 2011—2 years, $8.15 million)
- DH Mark Trumbo (Jan. 20, 2017—3 years, $37.5 million) re-signed
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Boston Red Sox
4 of 30
Worst Signing: 3B Pablo Sandoval
Date: November 25, 2014
Terms: Five years, $95 million
The Carl Crawford signing would have been a strong contender here if the Red Sox hadn't managed to unload him on the Los Angeles Dodgers.
With that, Pablo Sandoval is the easy choice.
Weight issues and a shoulder injury left him as a shell of his former self during his time in Boston.
He hit .237/.286/.360 for a 71 OPS+ before he was released on July 19, 2017, with two-and-a-half years and roughly $48 million left on his contract.
Other Bad Free-Agent Signings
- OF Mike Cameron (Dec. 14, 2009—2 years, $15.5 million)
- OF Carl Crawford (Dec. 11, 2010—7 years, $142 million)
- SP Ryan Dempster (Dec. 19, 2012—2 years, $26.5 million)
- RP Bobby Jenks (Dec. 21, 2010—2 years, $12 million)
- 1B Hanley Ramirez (Nov. 25, 2014—4 years, $88 million)
Chicago Cubs
5 of 30
Worst Signing: RF Milton Bradley
Date: January 9, 2009
Terms: Three years, $30 million
Milton Bradley led the AL in on-base percentage (.436), OPS (.999) and OPS+ (162) during the 2008 season with the Texas Rangers.
However, from forgetting how many outs there were and throwing a ball into the stands, to getting sent home mid-game after attacking a Gatorade cooler, to finally being suspended for the remainder of the season on Sept. 20 when he criticized the Cubs organization to the media, his first and only season in Chicago was an unmitigated disaster.
He was flipped for a bad contract—Carlos Silva of the Seattle Mariners—during the offseason.
Other Bad Free-Agent Signings
- SP Tyler Chatwood (Dec. 7, 2017—3 years, $38 million)
- RF Jason Heyward (Dec. 15, 2015—8 years, $184 million)
- SP Edwin Jackson (Jan. 2, 2013—4 years, $52 million)
Chicago White Sox
6 of 30
Worst Signing: 1B Adam LaRoche
Date: November 25, 2014
Terms: Two years, $25 million
After posting a 124 OPS+ with 26 home runs and 92 RBI in his final season with the Washington Nationals, Adam LaRoche was one of the better bats in the 2014-15 free-agent class.
The White Sox scooped him up on a two-year deal, and he promptly forgot how to hit, struggling to a 78 OPS+ with just 12 home runs and 44 RBI in 127 games in 2015.
Following that disappointing debut in Chicago, LaRoche made the surprising decision to retire after the White Sox announced that his son, Drake, would no longer be allowed in the clubhouse. It was eventually revealed that decision stemmed from complaints from several players about his son's "constant presence" in the locker room.
In the end, his early retirement saved the White Sox a hefty $13 million, but it still stands as their worst signing of the past decade.
Other Bad Free-Agent Signings
- OF Melky Cabrera (Dec. 16, 2014—3 years, $42 million)
- DH Adam Dunn (Dec. 3, 2010—4 years, $56 million)
- IF Jeff Keppinger (Dec. 10, 2012—3 years, $12 million)
Cincinnati Reds
7 of 30
Worst Signing: RP Ryan Madson
Date: January 13, 2012
Terms: One-year, $8.5 million
Not since lefty Eric Milton signed a three-year, $25.5 million deal prior to the 2005 season have the Reds handed out an awful free-agent contract.
In terms of bad signings over the past decade, the $8.5 million they wasted on Ryan Madson stands out as their worst free-agency move.
Madson closed out an excellent nine-year run with the Phillies in 2011 by converting 32 of 34 save chances. Despite that strong performance, he wound up settling for a one-year deal with the Reds in free agency.
While the signing looked like a bargain at the time, things quickly went south. Madson suffered a torn ligament in his right elbow during spring training and Tommy John surgery effectively ended his time in Cincinnati before it even started.
Other Bad Free-Agent Signings
- None
Cleveland Indians
8 of 30
Worst Signing: 1B/OF Nick Swisher
Date: January 3, 2013
Terms: Four years, $56 million
The Indians were uncharacteristically major players on the 2012-13 free-agent market, signing both Nick Swisher (4/$56M) and Michael Bourn (4/$48M) to long-term deals after their respective markets were slow to develop.
Both players had solid first seasons in Cleveland, but their production quickly bottomed out from there.
On Aug. 7, 2015, they were packaged together along with $15 million and sent to the Atlanta Braves in exchange for the bad contract of Chris Johnson, who was owed $19.5 million.
Swisher finished his time in Cleveland with just 1.6 WAR, compared to 3.3 WAR from Bourn. That, coupled with the fact that he earned $2 million more per year, made him the clear choice for the No. 1 spot.
Other Bad Free-Agent Signings
- OF Michael Bourn (Feb. 15, 2013—4 years, $48 million)
- OF David Murphy (Nov. 25, 2013—2 years, $12 million)
- SP Brett Myers (Jan. 4, 2013—1 year, $7 million)
- RP Kerry Wood (Dec. 10, 2008—2 years, $20.5 million)
Colorado Rockies
9 of 30
Worst Signing: 1B/OF Ian Desmond
Date: December 13, 2016
Terms: Five years, $70 million
Signing Ian Desmond to a five-year, $70 million deal looked like an ill-advised move by the Rockies at the time. Two years and minus-1.7 WAR later, nothing has changed.
After overplaying his hand during his first go-around in free agency the previous offseason and settling for a one-year, $8 million deal from the Texas Rangers, Desmond played his way into another qualifying offer with a 104 OPS+ that included 22 home runs and 21 steals amid a transition to the outfield.
Injuries derailed his first season in Colorado, but he was healthy in 2018 and still struggled, hitting .236/.307/.422 over 619 plate appearances for an 83 OPS+.
With three years and $38 million left, there's still time for him to salvage the deal. For now, it's an easy choice for the top spot.
Other Bad Free-Agent Signings
- SP Jorge De La Rosa (Dec. 3, 2010—2 years, $21.5 million) re-signed
- RP Mike Dunn (Dec. 15, 2016—3 years, $19 million)
- RP Boone Logan (Dec. 16, 2013—3 years, $16.5 million)
- RP Jason Motte (Dec. 8, 2015—2 years, $10 million)
- OF Gerardo Parra (Jan. 20, 2016—3 years, $27.5 million)
Detroit Tigers
10 of 30
Worst Signing: DH Victor Martinez
Date: November 14, 2014
Terms: Four years, $68 million (re-signed)
The first four-year deal that Victor Martinez signed with the Tigers would be a candidate for the team's best free-agent signing of the past decade.
In the final year of that contract, he hit .335/.409/.565 with 33 doubles, 32 home runs and 103 RBI to finish second in AL MVP voting and post 5.5 WAR.
The Tigers then rewarded him with another four-year deal ahead of his age-36 season, and a rapid decline in production followed. In three of the four years of his second contract, he posted an OPS under .700 and an OPS+ below 90, finishing with a combined .262/.320/.397 line while averaging 14 home runs and 63 RBI per year.
Lesson: Don't pay an aging star for past production.
Other Bad Free-Agent Signings
- 1B Prince Fielder (Jan. 26, 2012—9 years, $214 million)
- RP Mark Lowe (Dec. 8, 2015—2 years, $11 million)
- RP Joe Nathan (Dec. 4, 2013—2 years, $20 million)
- SP Mike Pelfrey (Dec. 6, 2015—2 years, $16 million)
- SP Anibal Sanchez (Dec. 17, 2012—5 years, $80 million)
- SP Jordan Zimmermann (Nov. 30, 2015—5 years, $110 million)
Houston Astros
11 of 30
Worst Signing: OF Colby Rasmus
Date: November 13, 2015
Terms: One-year, $15.8 million (qualifying offer)
The Astros spent a good chunk of the past decade rebuilding before a recent return to prominence, and that resurgence came largely on the strength of homegrown talent and a few shrewd moves on the trade market.
As a result, bad free-agent signings have been few and far between, so we're going to widen our scope a bit to include the qualifying offer that Colby Rasmus accepted following the 2015 season. Technically, he was granted free agency on Nov. 2, 2015. So even though he never hit the open market, he qualifies for inclusion under our stipulations.
Rasmus was a key cog for the Astros during their unexpected run to the postseason in 2015, posting a 116 OPS+ with 25 home runs and 2.8 WAR.
While he played stellar defense (20 DRS, 21.7 UZR/150) upon returning, his offensive game dried up, and he hit just .206/.286/.355 with 15 home runs.
Other Bad Free-Agent Signings
- IF Jed Lowrie (Dec. 15, 2014—3 years, $23 million)
- RP Brandon Lyon (Dec. 12, 2009—3 years, $15 million)
Kansas City Royals
12 of 30
Worst Signing: SP Ian Kennedy
Date: January 29, 2016
Terms: Five years, $70 million
A case can be made for the Alex Gordon re-signing as the pick for the Royals.
Then again, Gordon was a franchise icon who had just helped deliver a World Series and ended up signing for below market value, so it's tough to fault the Royals for bringing him back.
Instead, Ian Kennedy is the clear choice.
The Royals gave up a draft pick to sign Kennedy to a five-year deal after he posted a 4.28 ERA and 1.30 WHIP in 195.2 innings in his final season with the San Diego Padres to earn a qualifying offer.
He hasn't been terrible in Kansas City, posting a 4.49 ERA and 1.30 WHIP while averaging 156 innings in three seasons. That's hardly worth $14 million per year from a small-market team, though, and it's now an albatross contract amid a rebuild.
Other Bad Free-Agent Signings
- SP Noel Arguelles (Dec. 6, 2009—5 years, $7 million)
- OF Alex Gordon (Jan. 6, 2016—4 years, $72 million) re-signed
- SP Jason Hammel (Feb. 8, 2017—2 years, $16 million)
- 2B Omar Infante (Dec. 16, 2013—4 years, $30 million)
- SP Chris Young (Dec. 7, 2015—2 years, $11.5 million) re-signed
- SP Travis Wood (Feb. 15, 2017—2 years, $12 million)
Los Angeles Angels
13 of 30
Worst Signing: LF Josh Hamilton
Date: December 15, 2012
Terms: Five years, $123 million
It would be easy to call Albert Pujols the worst signing of the past decade for the Angels, especially since they still have three years and $87 million left to pay out.
However, Pujols was at least productive over the first half of that megadeal, posting a 123 OPS+ and averaging 29 home runs, 98 RBI and 2.9 WAR.
On the other hand, the Josh Hamilton signing was more or less a sunk cost from the get-go.
After posting 2.8 WAR in two seasons with the Angels, the team paid $68.4 million of the $74.4 million left on his contract to facilitate a trade with the Texas Rangers.
It doesn't get much worse than spending nearly $70 million for someone to play elsewhere.
Other Bad Free-Agent Signings
- SP Joe Blanton (Dec. 12, 2012—2 years, $15 million)
- 1B Albert Pujols (Dec. 8, 2011—10 years, $250 million)
Los Angeles Dodgers
14 of 30
Worst Signing: SP Scott Kazmir
Date: December 30, 2015
Terms: Three years, $48 million
After seemingly flaming out due to injuries, Scott Kazmir rose from the ashes—or in his case, independent ball—in 2013, and then he signed a two-year, $22 million deal with the Oakland Athletics that offseason.
When the left-hander proved healthy and productive over the life of that contract, teams were much more willing to open their wallets during his next foray into free agency, and the Dodgers ended up inking him to a three-year, $48 million deal.
The left-hander turned in a subpar 4.56 ERA and 1.36 WHIP over 136.1 innings in 2016 and then missed the entire 2017 season with a hip injury. He was shipped to the Atlanta Braves last winter along with Adrian Gonzalez and Brandon McCarthy in a swap of bad contracts for Matt Kemp, and then he was released before Opening Day.
Other Bad Free-Agent Signings
- SP Brett Anderson (Nov. 13, 2015—1 year, $15.8 million) qualifying offer
- IF Erisbel Arruebarrena (Feb. 21, 2014—5 years, $25 million)
- OF Alex Guerrero (Oct. 21, 2013—4 years, $28 million)
- SP Brandon McCarthy (Dec. 16, 2014—4 years, $48 million)
- OF Manny Ramirez (March 4, 2009—2 years, $45 million) re-signed
- RP Yaisel Sierra (Feb. 21, 2016—6 years, $30 million)
- RP Brian Wilson (Dec. 7, 2013—1 year, $10 million) re-signed
Miami Marlins
15 of 30
Worst Signing: SP Wei-Yin Chen
Date: January 19, 2016
Terms: Five years, $80 million
Strong seasons with the Baltimore Orioles in 2014 and 2015 earned Wei-Yin Chen a qualifying offer ahead of the 2015-16 offseason, but that didn't deter a Marlins team with legitimate hopes of contention from signing him to a five-year deal.
Things went poorly for player and team in 2016, and they've only gotten worse since.
The Marlins won just 79 games and Chen struggled to a 4.96 ERA over 22 starts in his first season in Miami. Injuries then limited him to 33 innings in 2017, and the Marlins went 77-85. And last year, after an offseason firesale, Chen went 6-12 with a 4.79 ERA for a 98-loss team.
With a backloaded deal that will pay him $42 million over the final two years, his contract looks as immovable as any in baseball.
Other Bad Free-Agent Signings
- RP Heath Bell (Dec. 5, 2011—3 years, $27 million)
- SS Jose Reyes (Dec. 7, 2011—6 years, $106 million)
- C Jarrod Saltalamacchia (Dec. 6, 2013—3 years, $21 million)
- RP Junichi Tazawa (Feb. 16, 2016—2 years, $12 million)
- SP Edinson Volquez (Dec. 1, 2016—2 years, $22 million)
Milwaukee Brewers
16 of 30
Worst Signing: SP Matt Garza
Date: January 26, 2014
Terms: Four years, $50 million
Matt Garza was arguably the top free-agent starter in a thin 2013-14 free agent crop that also included Ubaldo Jimenez, Ervin Santana, A.J. Burnett and Ricky Nolasco.
The fiery right-hander entered the 2014 season with a 3.84 ERA and 1.28 WHIP over 1,182.1 innings for the Twins, Rays and Cubs, and entering his age-30 season, he looked like a potentially game-changing addition to the Milwaukee rotation.
While he pitched to a solid 3.64 ERA and 1.18 WHIP in 27 starts during the first season of a four-year pact, he was hit hard over the final three years, struggling to a 5.10 ERA and 1.51 WHIP while allowing 10.2 H/9 and averaging 122 innings.
For a Brewers team that rarely dove into the deep end of the free-agent pool, Garza proved to be a prohibitive sunk cost.
Other Bad Free-Agent Signings
- RP Neftali Feliz (Jan. 19, 2017—1 year, $5.35 million)
Minnesota Twins
17 of 30
Worst Signing: SP Ricky Nolasco
Date: December 3, 2013
Terms: Four years, $49 million
Ricky Nolasco parlayed a terrific 2013 season with the Marlins and Dodgers into a $49 million deal from the shallow-pocketed Twins.
He took the ball on Opening Day in his Twins debut and allowed 10 hits and five earned runs in six innings to earn the loss. It would be a sign of things to come, as he finished his first season in Minnesota with a 5.38 ERA and 1.52 WHIP in 27 starts.
Things went from bad to worse when injuries limited him to just 37.1 innings in 2015, and he struggled upon returning to full health with a 5.13 ERA in 21 starts the following year before he was finally packaged with top prospect Alex Meyer and shipped to the Angels in a salary dump.
Other Bad Free-Agent Signings
- 1B Logan Morrison (Feb. 28, 2018—1 year, $6.5 million)
- IF Tsuyoshi Nishioka (Dec. 16, 2010—3 years, $9 million)
- DH Byung Ho Park (Dec. 1, 2015—4 years, $12 million)
New York Mets
18 of 30
Worst Signing: OF Jason Bay
Date: December 29, 2009
Terms: Four years, $66 million
From his NL Rookie of the Year season in 2004 through his one full season with the Red Sox in 2009, Jason Bay posted a 131 OPS+ while averaging 31 doubles, 30 home runs, 99 RBI and 3.6 WAR.
The Mets couldn't possibly have expected him to be such a colossal bust.
Injuries immediately took a significant bite out of his production, and in his three seasons in New York, he averaged just 96 games and hit .234/.318/.369 for a 90 OPS+ and a paltry 1.8 WAR.
He was released on Nov. 7, 2012, with the Mets eating the final $18.1 million of his contract on top of a $3 million buyout on a 2014 vesting option.
Other Bad Free-Agent Signings
- OF Michael Cuddyer (Nov. 10, 2014—2 years, $21 million)
- SP Oliver Perez (Feb. 2, 2009—3 years, $36 million) re-signed
New York Yankees
19 of 30
Worst Signing: CF Jacoby Ellsbury
Date: December 7, 2013
Terms: Seven years, $153 million
Seven years after signing Johnny Damon away from the rival Red Sox, the Yankees were at it again, luring Jacoby Ellsbury to the Bronx with a massive seven-year deal.
That allocation of funds effectively spelled the end of the Robinson Cano era, with the Yankees' longtime second baseman inking a 10-year deal with the Seattle Mariners five days later.
After a productive first season in New York where he posted a 111 OPS+ with 16 home runs, 39 steals and 3.6 WAR, Ellsbury quickly turned into a financial burden. He averaged an 89 OPS+ and posted a pair of sub-2.0 WAR seasons from 2015 to '17. He then missed the entire 2018 season with a torn labrum in his left hip.
He has two years and $42.3 million left on the contract, along with a $21 million club option for 2021 that carries a $5 million buyout.
Other Bad Free-Agent Signings
- SP A.J. Burnett (Dec. 11, 2008—5 years, $82.5 million)
- RP Pedro Feliciano (Jan. 3, 2012—2 years, $8 million)
- 3B Chase Headley (Dec. 15, 2014—4 years, $52 million)
- RP Damaso Marte (Nov. 12, 2008—3 years, $12 million)
- 1B/3B Kevin Youkilis (Dec. 14, 2012—1 year, $12 million)
Oakland Athletics
20 of 30
Worst Signing: DH Billy Butler
Date: November 19, 2014
Terms: Three years, $30 million
For a team that rarely spent significant money in free agency, the A's decision to give designated hitter Billy Butler $30 million over three years was a head-scratcher.
His final season in Kansas City had been mediocre at best. He posted a 96 OPS+ with just nine home runs and 66 RBI in 603 plate appearances—extremely lackluster power production at a power-centric position.
Sure enough, it was more of the same in his first season in Oakland, with a 98 OPS+ and 15 home runs to show for his 601 trips to the plate.
Butler was released on Sept. 11, 2016, with the A's eating the final year of a contract that looked like a bad idea from the start.
Other Bad Free-Agent Signings
- RP Santiago Casilla (Jan. 20, 2017—2 years, $11 million)
- SS Hiroyuki Nakajima (Dec. 17, 2012—2 years, $6.5 million)
- SP Ben Sheets (Jan. 26, 2010—1 year, $10 million)
Philadelphia Phillies
21 of 30
Worst Signing: RP Jonathan Papelbon
Date: November 14, 2011
Terms: Four years, $50 million
This one is more about the state of the franchise than the player's individual performance.
In his three-and-a-half seasons in Philadelphia, Jonathan Papelbon made a pair of All-Star appearances while posting a 2.31 ERA, 1.02 WHIP and 9.5 K/9. He converted 123 of 138 save chances and, by all accounts, was one of the game's better closers.
An aging Phillies team was clearly headed for a rebuild, though, and signing a closer to a contract that was the richest ever for a reliever at the time made no sense.
After winning 102 games in 2011, the Phillies went 81-81 during Papelbon's first year with the team. By the time he was finally traded midway through the 2015 season, he was playing for a Phillies team that was on its way to a 99-loss season.
Other Bad Free-Agent Signings
- SP A.J. Burnett (Feb. 16, 2014—1 year, $16 million)
- SP Jeremy Hellickson (Nov. 14, 2016—1 year, $17.2 million) qualifying offer
- OF Michael Saunders (Jan. 19, 2017—1 year, $9 million)
Pittsburgh Pirates
22 of 30
Worst Signing: 1B Lyle Overbay
Date: December 12, 2010
Terms: One-year, $5 million
The pickings are slim when it comes to bad free-agent signings by the Pittsburgh Pirates.
That said, while a one-year, $5 million deal might seem like peanuts to most teams, it was enough to make Lyle Overbay the fourth-highest-paid player on the Pittsburgh roster in 2011.
After posting a 105 OPS+ with 37 doubles and 20 home runs for the Blue Jays the previous season, Overbay made his Pirates debut hitting in the cleanup spot in the batting order.
As the season progressed, he slowly slid down the lineup, and when he was eventually released on Aug. 5, he was hitting .227/.300/.349 with eight home runs in 391 plate appearances for minus-0.6 WAR.
Other Bad Free-Agent Signings
- C Rod Barajas (Nov. 10, 2011—1 year, $4 million)
- SS Clint Barmes (Nov. 21, 2011—2 years, $10.5 million)
- SP Erik Bedard (Dec. 7, 2011—1 year, $4.5 million)
- RP Daniel Hudson (Dec. 21, 2016—2 years, $11 million)
San Diego Padres
23 of 30
Worst Signing: 1B Eric Hosmer
Date: February 19, 2018
Terms: Eight years, $144 million
Eric Hosmer still has seven years to prove he doesn't belong on this list.
That said, after hitting .253/.322/.398 for a 99 OPS+ with 18 home runs and 69 RBI in his Padres debut—good for 1.4 WAR at a cost of $21 million—he has his work cut out for him.
Making matters worse, signing him pushed Wil Myers off first base, which meant shuffling him all over the diamond last season in search of a long-term home. It also blocked prospect Josh Naylor, who hit .297/.383/.447 with 17 home runs and 74 RBI as a 21-year-old at Double-A.
General manager A.J. Preller has set the Padres up for long-term success with his impressive restocking of the farm system. This signing could really be a burden in the years to come, though.
Other Bad Free-Agent Signings
- 2B Orlando Hudson (Dec. 20, 2010—2 years, $11.5 million)
- SP Jered Weaver (Feb. 19, 2017—1 year, $3 million)
San Francisco Giants
24 of 30
Worst Signing: RP Mark Melancon
Date: December 5, 2016
Terms: Four years, $62 million
There were several to choose from here.
The decision to reward Angel Pagan (4/$40M) and Marco Scutaro (3/$20M) for their roles in winning the 2012 World Series backfired, as did the spending spree that added Johnny Cueto and Jeff Samardzija to the starting rotation during the 2015-16 offseason. However, it's an ill-advised signing from the next winter that earns the No. 1 spot.
After saving 130 games in four seasons with the Pirates, Mark Melancon looked like a slam-dunk addition to the back of a beleaguered bullpen.
Instead, he's converted just 14 saves in 23 chances during his first two years with the team, and he was essentially a $20 million middle reliever in 2018.
Other Bad Free-Agent Signings
- SP Johnny Cueto (Dec. 15, 2015—6 years, $130 million)
- 2B Mark DeRosa (Dec. 28, 2009—2 years, $12 million)
- 1B Aubrey Huff (Nov. 23, 2010—2 years, $22 million) re-signed
- OF Angel Pagan (Dec. 7, 2012—4 years, $40 million) re-signed
- SP Jake Peavy (Dec. 23, 2014—2 years, $24 million) re-signed
- SP Jeff Samardzija (Dec. 9, 2015—5 years, $90 million)
- 2B Marco Scutaro (Dec. 6, 2012—3 years, $20 million) re-signed
- OF Denard Span (Jan. 7, 2016—3 years, $31 million)
Seattle Mariners
25 of 30
Worst Signing: UT Chone Figgins
Date: December 8, 2009
Terms: Four years, $36 million
Chone Figgins picked the perfect time for a 7.7 WAR season.
In his contract year with the Angels, the versatile Figgins hit .298 and led the AL with 101 walks on his way to a .395 on-base percentage. He also finished third in the AL with 42 steals and scored 114 runs as one of the most dangerous table-setters in the game.
His numbers dipped across the board during his first season in Seattle.
The lofty walk rate that had driven his offensive value the previous year dropped from 13.9 to 10.5 percent, which further exposed his lack of power en route to an 84 OPS+. That would prove to be far and away his best season in a Mariners uniform.
Over the final three years of the deal, he played in just 147 games total, hitting a disastrous .185/.249/.253 in 507 plate appearances for minus-2.1 WAR.
Other Bad Free-Agent Signings
- OF Corey Hart (Dec. 13, 2013—1 year, $6 million)
- RP Juan Nicasio (Dec. 20, 2017—2 years, $17 million)
- RP Marc Rzepczynski (Dec. 3, 2016—2 years, $11 million)
St. Louis Cardinals
26 of 30
Worst Signing: OF Dexter Fowler
Date: December 9, 2016
Terms: Five years, $82.5 million
Can Dexter Fowler still salvage his time in St. Louis?
For all that's been made of his struggles this past season, he's just a year removed from posting a 122 OPS+ with a career-high 18 home runs and 64 RBI in his Cardinals debut.
However, after struggling mightily to the tune of a .180/.278/.298 line over 334 plate appearances and minus-1.4 WAR in 2018, his deal has quickly become one of the most maligned in baseball.
Making matters worse, the emergence of Harrison Bader and Tyler O'Neill alongside prized trade acquisition Marcell Ozuna has left Fowler as an impediment from a roster standpoint.
He'll be given every chance to right the ship in 2019, and he's capable of doing just that. For now, though, he's the clear choice.
Other Bad Free-Agent Signings
- RP Brett Cecil (Nov. 21, 2016—4 years, $30.5 million)
- SS Jhonny Peralta (Nov. 24, 2013—4 years, $53 million)
Tampa Bay Rays
27 of 30
Worst Signing: DH Pat Burrell
Date: January 5, 2009
Terms: Two years, $16 million
This is another contract that would qualify as pocket change for a bigger-market team but represented a major expenditure for the budget-conscious Rays.
To that point, Pat Burrell was the third-highest-paid player on the Opening Day roster in 2009 and 2010.
After posting an 81 OPS+ with 14 home runs and 64 RBI in the first year of the deal, he was designated for assignment on May 15, 2010, and eventually granted free agency after clearing waivers.
A few days later, he signed with San Francisco Giants, where he posted a 136 OPS+ with 18 home runs and 51 RBI in 96 games to help them to a World Series title.
Other Bad Free-Agent Signings
- 1B James Loney (Jan. 3, 2014—3 years, $21 million)
- 1B Carlos Pena (Jan. 24, 2012—1 year, $7.25 million)
Texas Rangers
28 of 30
Worst Signing: OF/DH Shin-Soo Choo
Date: December 27, 2013
Terms: Seven years, $130 million
Shin-Soo Choo hasn't been bad during his time with the Rangers.
Five years into his seven-year pact, he has a 109 OPS+ and 7.5 WAR to his credit.
In fact, this past season was one of the best of his career, as he logged a 112 OPS+ with 30 doubles, 21 home runs, 62 RBI and 83 runs scored to earn his first All-Star appearance.
He simply hasn't lived up to a deal that will pay him $21 million annually in 2019 and 2020.
Other Bad Free-Agent Signings
- DH Lance Berkman (Jan. 7, 2013—1 year, $11 million)
- 1B Mike Napoli (Jan. 19, 2017—1 year, $8.5 million)
Toronto Blue Jays
29 of 30
Worst Signing: DH Kendrys Morales
Date: November 18, 2016
Terms: Three years, $33 million
The popular pick here might be Russell Martin and the five-year, $82 million deal that will pay him $20 million in its final year in 2019.
However, Martin has produced 7.6 WAR in his four seasons in Toronto, and the backloaded nature of that contract made sense for a Blue Jays team that was still very much in contention.
Instead, we'll go with the signing of Kendrys Morales to replace Edwin Encarnacion.
While the front office was still holding out hope of contending, the writing was on the wall that the window was closing. So rather than signing Morales to a three-year deal, why not look for a more short-term solution that could provide similar results?
After all, in his two seasons in Toronto, Morales has pedestrian a 104 OPS+ and he's averaged 24.5 home runs and 71 RBI. Now they're stuck paying him $12 million in 2019 as they start to rebuild.
Other Bad Free-Agent Signing
- OF Jose Bautista (Jan. 18, 2017—1 year, $18 million) re-signed
- IF Maicer Izturis (Nov. 8, 2012—3 years, $10 million)
- C Russell Martin (Nov. 18, 2014—5 years, $82 million)
Washington Nationals
30 of 30
Worst Signing: C Matt Wieters
Date: Feb. 24, 2017
Terms: Two years, $21 million
After accepting a $15.8 million qualifying offer in 2016, Matt Wieters was at the mercy of the free-agent market once the Orioles decided to cut him loose the following offseason.
While he wasn't able to match that annual value, he did find enough of a market to coax a two-year deal out of the catching-needy Nationals.
After posting a brutal 62 OPS+ in the first year of the deal, he battled injuries in 2018 to play in just 76 games, leaving the Nats to rely on the likes of Spencer Kieboom and Pedro Severino for much of the year.
All told, he produced an invisible 0.0 WAR on that $21 million investment.
Other Bad Free-Agent Signings
- OF Nate McLouth (Dec. 12, 2013—2 years, $10.75 million)
- OF Jayson Werth (Dec. 5, 2010—7 years, $126 million)
All stats courtesy of Baseball Reference and FanGraphs, unless otherwise noted. Contract info comes via Spotrac.
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