Gerrit Cole yankees
Danielle Parhizkaran-USA TODAY Sports

The Yankees have built a longstanding reputation and throwing around the big bucks when they want a certain player. But which contracts are among the richest in franchise history? Here’s the top of that list.

Richest contracts in Yankees history: No. 10-5

D.J. LeMahieu: six years, $90 million

D.J. LeMahieu originally signed with the Yankees after the 2017 season for just two years and $24 million. That immediately looked like an absolute steal for general manager Brian Cashman and New York.

Across 871 plate appearances during the life of this contract, LeMahieu slashed .336/.386/.536. It included 36 homers, 43 doubles, 129 RBI, and 150 runs scored. He also won the American League batting title in 2020 with a .364 average. After getting 8.2 fWAR from him, it was time for New York to pay up.

The first two years of this deal haven’t produced in the same way, though. In 1,220 trips to the plate, the infielder slash line dropped to .265/.353/.368. His power numbers were all about the same despite having nearly 350 more plate appearances: 22 homers, 42 doubles, 103 RBI, and 158 runs scored.

LeMahieu did add a Gold Glove to his mantle in 2022, but the Yankees need that bat to come alive in 2023.

Jason Giambi: seven years, $120 million

While it continued into his first year in the Bronx, Jason Giambi’s ability to hit for a high average didn’t travel with him from Oakland. After hitting .314 in 2002, he only hit above .250 once more during his tenure with New York (.271 in 2005).

But of course, a hitter’s value is much more than what their batting average is. Giambi proved his value plenty by finishing in the top 20 of American League MVP voting four times as a Yankee. And as long as he played in a full season, that dude was hitting his homers.

Giambi played in at least 135 games four times with the Yankees. He slugged 30-plus homers in a season every time. Three of those occasions included at least 37 dingers. A typical year from the first baseman included a .925 OPS, 30 homers, and 86 RBI.

CC Sabathia: five years, $122 million

In his initial arrival to the Bronx, CC Sabathia already had secured one of the richest contracts in Yankees history. With an opt-out after three seasons, New York wanted to make sure its southpaw ace didn’t go anywhere.

Outside of winning the World Series in 2009, Sabathia was the elite workhorse we had gotten used to seeing. He won no fewer than 19 games between 2009 and 2011 with a 3.18 ERA and 1.19 WHIP in 705 innings pitched. He also secured three straight top-four finishes in American League Cy Young voting.

Sabathia’s performance throughout this extension wasn’t nearly as effective, unfortunately. He did go 15-6 with a 3.38 ERA and was an All-Star in 2012. After that, though, he didn’t post an ERA below 4.70 in a season again until 2016 (3.91).

Jacob Ellsbury: seven years, $153 million

Well, this was an albatross of a deal, right? It’s almost like the Red Sox sent him to the Bronx to purposely sabotage the Yankees. In his final year with Boston, Ellsbury stole a league-leading 52 bases while hitting nine homers and 31 doubles with a .781 OPS. He was a crucial cog in Boston’s 2013 World Series title run.

Taking him from the Red Sox and installing him as New York’s center fielder was supposed to work two-fold — it’d strengthen the Yankees while weakening their rivals. Not so much.

Ellsbury wasn’t as good as he was earlier in his career, but he was still somewhat productive when on the field. It was the being-on-the-field part that was most challenging. Through 520 games played, the outfielder slashed .264/.330/.386. He averaged 10 homers, 22 doubles, 50 RBI, 68 runs scored, and 26 steals per season.

Not terrible, but when looking at how much he was paid, it was a disaster. Ellsbury also didn’t take the field for the final three years of this contract, which only made matters worse.

Masahiro Tanaka: seven years, $155 million

Although Masahiro Tanaka dealt with elbow issues during his time in the states, he was mostly a reliable arm for the Yankees every year. He made 20 starts as a rookie in 2014 and then took the hill at least 24 times each season outside of the pandemic-shortened 2020 campaign (he made 10 starts).

This included five seasons of at least 150 innings. As we’ve seen with Gerrit Cole, getting consistent innings from one of your top starters is a great advantage for any club. Tanaka’s best overall performance came in 2016. He set career-high marks for starts (31) and innings pitched (199.2) in a season. It was accompanied by a 14-4 record, a 3.07 ERA, and a 1.08 WHIP. He also finished seventh in AL Cy Young voting. That was the only time he registered votes for that award.

Richest contracts in Yankees history: No. 5-1

CC Sabathia: seven years, $161 million

Before he could sign that extension, CC had to get himself in pinstripes in the first place. Ahead of his trip to free agency during the 2008-09 offseason, many knew Sabathia was going to be a hot commodity. His last two seasons in 2007 and 2008 all but solidified this huge payday, too.

He started 69 games and tossed 494 innings between these two seasons. The left-hander posted a 36-17 record with a 2.95 ERA, 1.13 WHIP, and 8.4 strikeouts per nine innings. This included winning the 2007 AL Cy Young Award. But his legend really grew once Cleveland traded him to the Milwaukee Brewers at the ’08 trade deadline.

After that deal, Sabathia finished his year with an 11-2 record, a 1.65 ERA, and a 1.00 WHIP. He made 17 starts for the Brewers, and he racked up seven complete games (including three shutouts). That performance made him one of the best midseason pickups of all time. Cashman made sure to get his man that winter by having a face-to-face meeting with Sabathia in California, as well.

Mark Teixeira: eight years, $180 million

This was just another part of the Yankees’ offseason spending spree that helped lead to a 2009 World Series title. New York had just finished a long and expensive contract with Jason Giambi (which we can see above). Naturally, they went out and secured another first baseman for the long haul in Mark Teixeira.

Tex was a productive Yankee, as his tenure included four years of 30-plus homers and three straight 30-100 campaigns from 2009-11. None were better than his ’09 campaign, though. The switch hitter led the league with 39 homers and 122 RBI while slashing .292/.383/.565 with 43 doubles and 103 runs scored.

The first baseman earned an All-Star selection while also winning a Silver Slugger and Gold Glove. He finished second in AL MVP voting to Joe Mauer, but I think he’s happy taking the World Series title over that hardware.

Derek Jeter: 10 years, $189 million

Could there have ever been better leverage for a long-term extension than what Derek Jeter had following the 2000 season? He had just five full years in the big leagues, but it included one Rookie of the Year Award, three All-Star selections, and three top-10 AL MVP finishes.

Oh, yea — and four World Series titles in five years.

New York won just one title during the duration of this extension, but the organization had several legitimate opportunities. The same can’t be said about the Bronx Bombers right now.

This period of time included numerous top-10 MVP finishes, several All-Star Game appearances, five Gold Gloves, and four Silver Sluggers. Over the course of 6,983 plate appearances, Jeter slashed .310/.380/.445. A typical year included 16 homers, 32 doubles, 72 RBI, 108 runs scored, and 22 stolen bases.

Alex Rodriguez: 10 years, $275 million

Speaking of getting a contract extension with the Yankees at an opportune time, here’s Alex Rodriguez. Instead of opting into the rest of his then-record $252 million deal, he opted out and eventually negotiated an even bigger deal after his age-31 campaign.

That’ll happen when you’ve won three MVPs in a five-year span and just finished one of the most powerful Yankee offensive seasons ever. A-Rod led the league with 54 home runs, 156 RBI, 143 runs scored, and a 1.067 OPS en route to winning his final MVP Award.

The three seasons that followed between 2008 and 2010 were typical A-Rod, too. He slugged at least 30 homers with 100-plus RBI in each campaign while slashing .286/.378/.537 in 1,724 plate appearances. Rodriguez was also a crucial piece of New York’s 2009 World Series run.

In 68 postseason plate appearances that year, the third baseman slashed .365/.500/.808 with six homers, 18 RBI, and 15 runs scored. But after 2010, things started going downhill. He appeared in 100-plus games just twice between then and the end of his career in 2016. This also included a year-long suspension in 2014 because of his involvement in the Biogenesis PED scandal.

Gerrit Cole: nine years, $324 million

Gerrit Cole is in the midst of this record-breaking deal as we write the original version of this article. While the 2022 season included a career-worst and league-leading 33 home runs allowed, the right-hander has been a consistent cog in New York’s rotation since 2020.

This has included two top-five finishes in AL Cy Young Award voting in 2020 and 2021. Although his postseason performance includes a rough showing against the Red Sox in the 2021 AL Wild Card Game, he came back with a vengeance to be the staff ace this past October.

Cole pitched to a 2.95 ERA and 1.04 WHIP in 18.1 postseason innings for the Yankees. He won both his starts in the ALDS against the Cleveland Guardians. One was in Game 4 when the Yankees had their backs against the wall.

Matt Musico can be reached at [email protected] and you can follow him on Twitter: @mmusico8.

Matt Musico is an editor for ESNY. He’s been writing about baseball and the Mets for the past decade. His work has been featured on numberFire, MetsMerized Online, Bleacher Report, and Yahoo! Sports.