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How Have the Yankees Larger Ventures into Free Agency Fared Over the Past Decade?

How Have the Yankees Larger Ventures into Free Agency Fared Over the Past Decade?

By Chris O’Connor

November 23, 2021


Despite a potential lockout looming on December 1st, the offseason hot stove has seen some action over the past few weeks. Pitchers Eduardo Rodriguez, Noah Syndergard, and Justin Verlander have already secured large free agent deals while rumors have suggested that some of the bigger position-players like Corey Seager and Marcus Semien would like a new contract before the CBA expires. With the Yankees heavily involved in the bidding for many of the top free agents and trade candidates, I wanted to take a look back at the Yankees forays into free agency following their World Series win in 2009. For the purposes of this article, I wanted to focus on contracts for free agents worth over $50 million. While the Yankees should never be hamstrung by any contract, that is a nice round, baseline number for a large contract that can potentially limit roster flexibility. Extensions are not included.

2010-2011 offseason

Derek Jeter- 3 years, $51 million

After a difficult 2010 season that saw him slash just .270/.340/.370, the 36 year-old hit the free agent market with a return to the Yankees viewed as a certainty. Negotiations quickly went south, however, and Brian Cashman reportedly told Jeter to see if anyone else would beat the Yankees offer. Jeter eventually did re-sign on this deal that spanned the 2011-2013 seasons, but the relationship between the two was forever frayed. Jeter was surprisingly able to bounce back in 2011-2012, hitting .308 while accumulating 5.5 fWAR during the first two years of the contract. A fractured ankle that he suffered in the 2012 ALCS hobbled him throughout 2013 as injuries limited him to just 17 games. Fangraphs estimates his worth to be $34.7 million over those three years, so strictly from a production standpoint, he was not worth the contract. Still, his very good first two years and his total value and goodwill on the team makes this contract a no-brainer.

2013-2014 offseason

Jacoby Ellsbury- 7 years, $153 million

This contract has been the poster child for Brian Cashman skeptics, and I am sure that in recent years it has given the Yankees some level of hesitation to the idea of splurging in free agency. Ellsbury was merely decent for the first four years of the contract. From 2014-2017, he played an average of 130 games, hit for an OPS+ of 95, and accumulated 8.1 fWAR. That is certainly not good in the context of a $153 million contract, but that is about average production. Fangraphs estimates his value to be about $63 million over that span. However, due to a myriad of injuries and a legal battle with the Yankees, he never played another game for the team after 2017. This contract has a reputation as an unmitigated disaster, and deservedly so.

Brian McCann- 5 years, $85 million

McCann was a big signing for the Yankees at the time because they had a big need at the catcher position, having never really replaced Russell Martin after he left for the Pirates in 2013. From 2014-2016, McCann played an average of 135 games, hit 69 home runs, had an OPS+ of 99, played great defense behind the plate, and accumulated 8.2 fWAR. Fangraphs estimates his value to be $63.9 million over those three years when he was paid $51 million. After the breakout of Gary Sanchez in the second half of 2016, McCann was traded to the Astros that offseason for Albert Abreu and Jorge Guzman. Abreu is one of the Yankees better prospects and will look to break out with his excellent stuff in 2022, while Guzman was part of the trade that brought Giancarlo Stanton to the team. A very nice signing for the Yankees that continues to pay dividends.

Masahiro Tanaka- 7 years, $155 million

This was a great signing. Tanaka went 78-46 with a 3.74 ERA from 2014-2020 and his 18.9 fWAR during that span ranks 19th among all pitchers. He was an excellent postseason pitcher as well: in 10 starts, he went 5-4 with a 3.33 ERA, and that includes his two starts in 2020 when he gave up 11 runs in 8 innings. Tanaka was just a durable, reliable starter who came through in big moments. Fangraphs estimates his value to be about $150.2 million during the seven years, but that includes just $6.5 million for the shortened 2020, when he went 3-3 with a 3.56 ERA in 10 starts. From 2014-2019, his value was estimated to be $143.7 million, and it can be argued that his playoff performance during that span makes his value considerably higher. I would argue that this was one of the best $100+ million free agent contracts that any team has given a player.

2014-2015 offseason

Chase Headley- 4 years, $52 million

Headley was nothing if not consistent during his time with the Yankees. He came over in a mid-season trade from the Padres in 2014, and after a nice half-season with the Yankees, the team signed him to this contract as a free agent. From 2015-2017, he never played less than 140 games, hit between 11-14 home runs every year, and accumulated 6.3 fWAR. Fangraphs estimates his worth at about $49.9 million for those three years, after which he was traded back to the Padres. Nothing flashy about it, but Headley was just a solid player for his 3.5 years with the Yankees. This was definitely a nice signing for the team and player.

2016-2017 offseason

Aroldis Chapman- 5 years, $86 million

This contract is notable for the sequence of events leading up to it. With the Yankees floundering leading into the 2016 trade deadline, Brian Cashman got ownership approval to sell. He moved Chapman to the Cubs for a package headlined by Gleyber Torres, and while Chapman won a ring for the Cubs, the Yankees were able to re-sign him in the offseason. From 2017-2021, Chapman has 124 saves, a 2.82 ERA, and accumulated 6.3 fWAR. He actually opted out of the remaining two years on his contract after 2019, but quickly re-signed on a 3 year, $48 million deal. Assessing the value of a reliever is difficult as WAR does not consider leverage and context. Still, while Chapman has had a few notable blips for the team, particularly in the playoffs, he has been one of the best closers in the game since 2017. Maybe the Yankees should have earmarked this money for a starting pitcher, but Chapman has been very good for the team for a long time.

2017-2018 offseason

Giancarlo Stanton- 10 years, $265 million

While Stanton did come over in a trade with the Marlins, this was a pure salary dump. The Yankees gave up only Starlin Castro and two lower-level prospects, so for the sake of this article I will consider this a free-agent signing. Evaluating the 2020 season is difficult as the 6-game season skews counting stats. Stanton played in 23 games that season with a .887 OPS, but he really showed out in the playoffs with 6 home runs and 13 RBI’s in 7 games. Stanton notably struggled through an injury-plagued 2019 where he played in only 18 games, which is certainly a case against him. But in 2018 and 2021, he played in 297 games, hit 73 home runs and 197 RBI’s, and accumulated 6.9 fWAR. During those two seasons, Fangraphs estimates his value at about $55.5 million when he was actually paid $54 million. If you include 2019, he was worth $58.4 million and actually paid $80 million. I think that it is pretty clear that the Yankees would not take on this contract again if they had the chance, but that does not mean that Stanton cannot have value moving forward. If he can stay healthy and continue to mash, he can be a huge piece in the lineup for years to come.

2019-2020 offseason

Gerrit Cole- 9 years, $324 million

The 2020 season makes the counting stats question difficult, but in two seasons with the Yankees, Cole has gone 23-11 with a 3.11 ERA in 42 starts. While he has been a tad inconsistent, Cole has indeed been the ace that the Yankees paid for. With 5.3 fWAR in 2021, Fangraphs estimates his worth at $42.1 million when he was actually paid $36 million. He pitched well in the playoffs in 2020, but his meltdown in the 2021 Wild Card game is one that will stand in the minds of many until he becomes through in the postseason. Giancarlo Stanton was a similar scapegoat after the 2018 ALDS loss to the Red Sox, but he has bounced back in the postseason in a big way. Cole has a track record of playoff success, so I am confident that it was a one-time blip.

2020-2021 offseason

D.J. LeMahieu- 6 years, $90 million

The purpose of LeMahieu’s high number of years and low AAV was to lower his hit on the luxury tax payroll. While LeMahieu struggled to repeat his MVP-level performance in 2021, he still stayed healthy enough to play 150 games, hit at about a league-average level, played good defense, and accumulated 2.4 fWAR. Fangraphs estimates his worth to be about $19.5 million in 2021 while he actually made $15 million, so he still was a net positive for the team. But he will turn 34 in 2022 and saw a worrying decline in performance. That may have been due to the sports hernia that he played through; can he bounce back?


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