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It’s the fiery heart of Major League Baseball’s offseason hot stove. This is when general managers talk trades at the Winter Meetings, while top free agents find new teams for next season. However, just because your favorite franchise shells out big bucks for an ace pitcher or power hitter, doesn’t mean it will actually make the team better the following season.

We here at The Props Network are covering the betting odds implications of this offseason’s crop of MLB free agents. We’re also in a reflective mood. The last days of this dying decade have inspired us to look back for lessons from the past. Specifically, bad free agent contracts from the past 10 years that did nothing to help the teams that gave them out. 

Recently, ESPN’s David Schoenfield gave his picks for the best and worst free-agent signings of the decade for all 30 MLB teams. So, over three articles, we will break down Schoenfield’s list into the worst contracts of the AL/NL East, AL/NL Central, and AL/NL West :

The five worst AL East contracts:

Boston Red Sox

Contract: Pablo Sandoval, 2015 (5 years, $95 million)

Impact on team wins: Boston went 71-91 in 2014, and 78-84 in 2015. Sandoval compiled 3.4 WAR in 2014, but only -0.9 WAR in 2015. 

Schoenfield: “The $142 million contract for Carl Crawford in 2011 was one of the worst in history (Crawford was worth just 3.7 WAR over the life of the deal), but at least the Red Sox were able to dump Crawford on the Dodgers two years later. So the worst deal goes to Sandoval, who for $95 million produced negative WAR with the Red Sox before he was released after two-plus seasons. (Hanley Ramirez takes third-place honors.)”

Other takes: In July 2017, Sports Illustrated’s Jon Tayler wrote, “Of all the players in league history to sign a deal of $95 million or more, only he and Ryan Howard produced negative value over the length of it; Howard edges him out, worth -4.5 WAR while pulling in $125 million from the Phillies from 2012 to ’16.

Sandoval was not as big a monetary loss as Boston’s other notable free-agent disaster, Carl Crawford, who got $142 million and lasted only 161 awful games (the same as Sandoval, oddly enough) in Boston before being shipped to the Dodgers in 2012.

But Crawford at least was instrumental in that Los Angeles deal, which helped the franchise clear the books during that lost season and restock ahead of a World Series-winning campaign in ’13. Sandoval will do no such thing for Boston: He is a lost cause, through and through.

New York Yankees

Contract: Jacoby Ellsbury, 2014 (7 years, $153 million)

Impact on team wins: New York went 85-77 in 2013, and 84-78 in 2014. Ellsbury compiled 5.8 WAR in 2013, but only 3.3 WAR in 2014.

Schoenfield: “The Ellsbury deal looked risky from the beginning, a player who had a monster 2011 season when he finished second in the MVP vote but one who had also battled injuries, playing 18 games in 2010 and 74 in 2012. He had a 3.6 WAR debut season with the Yankees, but it went downhill from there, and the seven-year contract will yield just 39 home runs and an average of just 74 games per season.”

Other takes: “In November 2019,’s Brendan Kuty wrote, “The Yankees handed a 30-year-old who whose value was in his legs a 10-figure deal that blew away anything anyone else was offering. They hoped he would be worth the money early in the deal, even if the last couple years proved sunken cost. Nope. E

llsbury was somewhere around average or less than that at the plate for three seasons before missing 2018 and 2019 with a never-ending list of injuries. That the Yankees cut him with $26 million remaining on his deal — $21 million for 2020, plus a $5 million bonus for turning down his 2021 option — puts Ellsbury at the top of our list [of 12 worst Yankees contracts ever].

Baltimore Orioles

Contract: Chris Davis, 2016 (7 years, $161 million)

Impact on team wins: Baltimore went 81-81 in 2015, and 89-73 in 2016. Davis compiled 5.2 WAR in 2015, but only 3.0 WAR in 2016. 

Schoenfield: “Davis hit 53 home runs in 2013, then got his big deal after hitting 47 in 2015. In between, however, was a .196 season, and that turned out to be the prophecy of what was to come.

He has hit .198 through the first four years of the contract and has been worth minus-0.4 WAR.

Other takes: In August 2018, The Sports Daily’s Matthew Orso wrote: “The production Davis has provided is not worth $161 million. It’s not even worth $161. And to a certain extent, the blame in regards to the deal should not fall onto the shoulders of Davis. No one forced the Orioles into giving him such a substantial contract. 

He has every right to reap the rewards he’s earned. But, from an analytical and statistical standpoint, signing Davis to this contract may end up being one of the biggest financial mistakes in baseball history.

Toronto Blue Jays

Contract: Jose Bautista, 2017 (1 year, $18 million)

Impact on team wins: Toronto went 89-73 in 2016, and 76-86 in 2017. Bautista compiled 1.0 WAR in 2016, but only -1.7 WAR in 2017.

Schoenfield: “After turning down a big offer in the spring of 2016 after hitting 40 home runs in 2015, Bautista had a mediocre 2016 and came crawling back to the Blue Jays on a one-year offer. He hit .203/.308/.366 in 157 games, and the Blue Jays fell from 89 wins to 76.

Other takes: In November 2017, SportsBreak’s Kean Doherty wrote, “Bautista did have many great years and moments for the franchise, all worthy of praise. But not worth the $18.5 million option the team picked up prior to the start of the 2017 season. Cracks already started to appear in the aging slugger’s game in 2016, but a playoff year makes everyone giddy — as well as the fact that Toronto couldn’t sign DH/1B Edwin Encarnacion. 

Bautista was more durable in 2017, playing in 157 games after just 116 in 2016. However, he finished below the Mendoza line with a .203 batting average and was 13th in baseball with 170 strikeouts (a dubious Jays’ record, too).

Joey Bats had just 23 homers and 65 RBI, a paltry .674 OPS and made the top 40 in grounding into double plays with 16.

Tampa Bay Rays

Contract: Johnny Damon ($5.25 million) and Manny Ramirez ($2 million), 2011

Impact on team wins: Tampa Bay went 96-66 in 2010, and 91-71 in 2011. Damon compiled 2.6 WAR in 2010, but only 2.3 WAR in 2011. Meanwhile, Ramirez compiled 0.8 WAR in 2010, but only -0.3 WAR in 2011. 

Schoenfield: “The money wasn’t big, but coming off a 96-win season and division title in 2010, the Rays gambled on the two veterans. Damon was OK with a 109 OPS+ over 150 games, but Ramirez played just five games, then retired after testing positive for a banned substance (and though he tried to come back, he never played in the majors again).

The Rays did make the playoffs with 91 wins — thanks to Evan Longoria ‘s dramatic walk-off home run on the final day of the season — but maybe they would have gone deeper in the playoffs if they had spent this money differently.

Other takes: In April 2011, Bleacher Report’s Steven Slivka wrote: “Nobody wanted to touch the washed-up Ramirez after the White Sox did not offer him a contract after the 2010 season. The Rays signed him to a one-year contract worth two million dollars prior to Spring Training of the 2011 season.

A far fall from the $45 million contract the Dodgers offered him two years prior. After a one-for-17 start to the 2011 season, an 0-6 team record and a positive drug test looming over him, it makes sense that Ramirez is walking away. After all, he left Boston and Los Angeles on sour notes, so it’s only fair that he walks away from baseball, in general, amidst harsh skepticism.

The five worst NL East contracts:

New York Mets

Contract: Yoenis Cespedes, 2017 (4 years, $110 million)

Impact on team wins: New York went 87-75 in 2016, and 70-92 in 2017. Cespedes compiled 2.9 WAR in 2016, but only 2.1 WAR in 2017.

Schoenfield: “We have a couple of choices here. The Jason Bay contract in 2010 was a disaster — four years, $66 million, 1.8 WAR — but the second Cespedes deal (after he opted out of a three-year, $75 million contract after one year) has been a more expensive calamity. Cespedes has been unable to stay healthy, playing just 119 games so far in three seasons, leading to a grievance resolved by hashing out a pay cut for 2019 and 2020.

Other takes: ” In June 2019, Bleacher Report’s Bob Klapisch wroteIt appeared the Wilpon family, notoriously unpopular with fans, caved to public pressure to sign Cespedes. But to be fair, they agreed to pay Cespedes strictly on general manager Sandy Alderson’s recommendation. Committing to Cespedes was one of two notable mistakes of Alderson’s regime with the Mets. The other was the three-year, $39 million deal awarded to Jay Bruce.

Atlanta Braves

Contract: B.J. Upton, 2013 (5 years, $75.25 million)

Impact on team wins: Atlanta went 94-68 in 2012, and 96-66 in 2013. Upton compiled 2.6 WAR in 2012, but only -1.8 WAR in 2013. 

Schoenfield: “Upton was a strange gamble for a franchise that doesn’t like to dip into free agency. He had been excellent in his age-22 and 23 seasons but had averaged just 2.1 WAR over the next four seasons, hitting under .250 with a ton of strikeouts each year.

In his walk year, he posted a .298 OBP. The Braves paid for the tools more than the on-field results. He fell apart in Atlanta, hitting .198 in his two seasons there before the Braves traded him to San Diego.

Other takes: In March 2017, Bleacher Report’s Zachary Rymer wrote, “When the Atlanta Braves signed Melvin Upton Jr. (then B.J. Upton) in November 2012, they were signing a guy coming off a career-high 28 homers who had also stolen 31 bases and logged a .752 OPS. In retrospect, they should have paid more attention to the .298 on-base percentage Upton had.

That encapsulated a handful of serious problems, such as a strikeout tendency that had always been there and plate discipline that had taken a turn for the worse. Despite his occasional flashes of brilliance, nobody had ever been able to call Upton a consistent player.

The deal was a disaster right away. Upton was one of the worst hitters and least valuable regulars in baseball in 2013.



Philadelphia Phillies

Contract: Carlos Santana, 2018 (3 years, $60 million)

Impact on team wins: Philadelphia went 66-96 in in 2017, and 80-82 in 2018. Santana compiled 3.4 WAR in 2017, but only 1.7 WAR in 2018. 

Schoenfield: “The Phillies tried to fit a square peg into a round hole with this signing, as it required moving Rhys Hoskins to left field so that they could play Santana at first. Hoskins was a big liability on defense and Santana had his worst season. He was traded after the season for Jean Segura, who promptly fell from 4.3 WAR with the Mariners to 1.3 with the Phillies.

Other takes: In January 2019, Let’s Go Tribe’s Matt Lyons wrote, “Across the board, Santana had one of his worst seasons ever with the Phillies [in 2018]. He slashed .229/.352/.414 for a wRC+ of 109 — the second-lowest of his career.

He still hit 24 home runs, though, and he drew walks 16.2 percent of the time (more on that in a minute) and struck out a career-low 13.7 percent. Probably not enough production for hungry Phillies fans who wanted $15 million worth of production out of him.

Miami Marlins

Contract: Wei-Yin Chen, 2016 (5 years, $80 million)

Impact on team wins: Miami went 71-91 in 2015, and 79-82 in 2016. Chen compiled 3.8 WAR in 2015, but only -0.1 WAR in 2016.

Schoenfield: “The Reyes contract certainly didn’t pan out — he produced just 9.1 WAR over the life of the deal — but the Marlins did trade him away. More inexplicable was giving Chen, a nice mid-rotation starter with the Orioles, an $80 million contract. The Marlins non-tendered him this offseason after 13 wins and a 5.10 ERA over three seasons.

Other Takes: In November 2019, Bleacher Report’s Joel Reuter wrote: “Not only did the Marlins vastly overpay to sign Chen, but they also surrendered a draft pick since he had rejected a qualifying offer from the Orioles. He has a 5.10 ERA over 358 innings so far during his time in Miami, and he was used exclusively as a reliever in 2019. There’s nothing like an expensive and ineffective middle reliever.

Washington Nationals

Contract: Nate McLouth, 2014 (2 years, $10.75 million)

Impact on team wins: Washington went 86-76 in 2013, and 96-66 in 2014. McLouth compiled 1.6 WAR in 2013, but only -0.7 WAR in 2014. 

Schoenfield: “Give Mike Rizzo credit: He has had very few misses in free agency, even on his one- and two-year deals. McLouth lasted just one year in D.C., hitting .173 with one home run in 73 games.

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