30 biggest free agent contracts in New York Yankees history

The dollar amounts that the New York Yankees, accused of "buying championships" throughout the '90s, have actually spent over the years may surprise you.

Or, more accurately, they'll warp your mind when you realize how much the game has changed since the mid-1990s.

What used to be an exorbitant free agent sum now misses the list of New York's top 30 signings, by total dollar value, entirely. Kenny Rogers and David Cone, who both signed during the 1995-96 offseason for $19.5 million (four years for Rogers, three for Cone), have seen their earth-shattering deals eclipsed by pedestrian modern contracts like Adam Ottavino's three-year, $27 million pact from 2019.

This free agency deep dive into the Yankees' behaviors is enlightening, and also helps illuminate how much cash it took to keep the Core Four together over the years.

Richest Contracts in New York Yankees History

HONORABLE MENTIONS:
Rafael Soriano, 2010: Three Years, $35 Million
JA Happ, 2018 (lol): Two Years, $34 Million
Randy Johnson, 2005: Two Years, $32 Million ($57 million total obligation, thanks to AZ)
Jose Contreras, 2003: Four Years, $32 Million (El Duque cost just $6.6 million over four years pre-1998)
Roger Clemens, 2007: One Year, $28 Million prorated down to $18.7 million for partial season (cool)
Danny Tartabull, 1992: Five Years, $25.5 Million
Dave Winfield, 1980: 10 Years, $23 Million (!!!, what)
Hideki Matsui, 2002: Three Years, $21 Million

So, what are we waiting for?! Let's spend as much as fans wish Hal Steinbrenner would dole out in one offseason, all within the confines of a single article!

30. Andrew Miller, 2014: Four Years, $36 Million

Miller didn't make it to the end of his Yankees contract in pinstripes, dealt to Cleveland midway through the team's 2016 sell-off. Predictably, he dominated that postseason as a multi-inning weapon, earning ALCS MVP honors by hurling 7.2 innings, whenever he was needed, and racking up 14 Ks.

The next October, of course, he let the Yankees back into the ALDS by surrendering a home run to Greg Bird, left-on-left, while holding a two-games-to-none lead. The Yanks won the series. Miller never got his due in the Bronx, and the 2015 team has been largely forgotten, but this deal was a great one.

29. Gary Sheffield, 2003: Three Years, $36-38 Million

Language surrounding Sheffield's Yankees deal at the time is confusing; Peter Gammons reported it as "between $36 and $38 million" at the time, while other outlets considered it to be $39 million.

Regardless, he's slotted in the right place. Don't question it.

Sheffield did nothing but mash after coming over from the Braves, adding intimidation and swagger to a somewhat stale Yankee lineup while drilling 36 and 34 homers in his first two seasons in the Bronx. By 2006, he was breaking down somewhat, and found himself dealt to Detroit for a package highlighted by ... Humberto Sánchez? It felt like a big deal at the time!

28. Zack Britton, 2019: Three Years, $39 Million

Prior to the 2019 season, the Yankees "shocked" onlookers by shelling out to keep Zack Britton, after acquiring the left-hander as a supposed rental during the summer of 2018.

He didn't make it to the end of the deal healthy, succumbing to elbow issues midway through the 2021 season (his contract, via triggered opt-ins, was eventually extended through 2022).

Britton will go down as a very fine Yankee who battled hard to get back to his position at the tail end of an injury-wrecked season last year. We'd rather have his 2019-20 seasons than Dillon Tate, whom the Yankees traded to Baltimore in exchange for his services.

27. Carl Pavano, 2005: Four Years, $39.95 Million

Wow, ranking the best contract in Yankees history 27th all time?! Where do these guys get off?!

Pavano was an unmitigated disaster in pinstripes -- and, it should be noted, grew up a Red Sox fan in New Britain, CT and started his career in the Red Sox organization.

The Yankees, after being embarrassed in 2004, paid for past performance (and outbid Boston) to secure Pavano's services coming off an 18-8, 3.00 ERA season where he put it all together in Florida. He only made 26 starts across four seasons with the Yankees, going 4-6 with a 4.77 ERA in 17 starts in his "fullest" season in '05.

Among Pavano's prime transgressions were sustaining a bruised buttocks in spring training and lying about a car accident, withholding from the Yankees the important information that he'd busted some ribs.

In other words, someone you definitely want cracking your Top 30 deals.

26. Mariano Rivera, 2001: Four Years, $39.99 Million

From the biggest bonehead to the biggest no-brainer, the Yankees secured the incredible Mariano Rivera for four additional years prior to the 2001 season.

During the duration of that contract, Rivera posted a 211 ERA+, made three All-Star teams ... and, yes, suffered his two highest-profile failures as a member of the Yankees in 2001 and 2004. He was still a God among men, though, and the Yanks wouldn't have made it as far as they did without him.

It's also not the final time he appears on this list.

25. Anthony Rizzo, 2022: Two Years, $40 Million

Bet you didn't expect to see the contract Anthony Rizzo just signed crack this list, huh?

His $32 million contract inked prior to 2022 just missed, too, and Rizzo opted out, added an extra million dollars per year this offseason, and secured $6 million worth of guaranteed buyout money if the team doesn't pick up his final option year for 2025.

Worth it to keep him away from the Astros. Rizzo will be a de facto sub-captain for the Yankees under Aaron Judge moving forward, as long as his dog Kevin approves.

24. Carlos Beltrán, 2013: Three Years, $45 Million

Wow. Truly sucks to see this here!

Beltrán's Yankees tenure was deeply strange. After regressing between 2013 and 2014 (who didn't?) and watching his OPS+ drop from 127 with the Cardinals to 98 with the Yankees, he picked it up and posted OPS+ marks of 119 and 122 the next two seasons, making the 2016 All-Star team.

After the season, he headed to the Astros, where he went on to implement the most comprehensive sign-stealing operation in MLB history after reportedly assuring Houston's front office that they were "behind" the Yankees in that department.

Beltrán also eventually went on to be the highest-paid YES Network announcer on this list.

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23. Mariano Rivera, 2007: Three Years, $45 Million

Mariano's second appearance on this list made him baseball's highest-paid closer and secured his place with the Yankees through their most recent World Series victory in 2009, something that -- once again -- they could not have done without him.

Again, worth every penny.

22. Kei Igawa, 2006: Five Years, $20 million ... Plus $26 Million Posting Fee. $46 Million Total Cost.

Perhaps Igawa doesn't technically belong this high, but it just ... felt right to discuss him here, considering the total money committed to his purchase would've been better spent in a bonfire.

Igawa was thought to be a high-upside No. 4 starter at worst when he came over from the Hanshin Tigers. Instead, he was more like a low-upside No. 9 starter. In two seasons where he made big-league appearances, Igawa subtracted 0.5 WAR from his Yankees teams, and wound up exiled to the high minors for years 3-5 of his contract.

Igawa became the veritable Mayor of Scranton, but that probably wasn't worth $46 million of the Yankees' money. It's the second-worst purchase the team has ever made, right behind the time they paid Kevin Brown $15 million to smash them in the knee with a wrench.

21. Jorge Posada, 2002: Five Years, $51 Million

Jorge Posada tested the waters of free agency after the 2001 season, but re-signed with the Yankees by early February at a massive cost. See how tough it was to keep this core together?!

Posada further blossomed into stardom on this contract, finishing third in the MVP race in 2003 by drilling 30 homers, slugging .518, getting on base at a .405 clip, and dinking a Pedro Martinez pitch into shallow center field to tie Game 7 of the 2003 ALCS (ok, fine, MVP voters didn't actually consider this, but it was cool as hell).

Posada will also appear on this list again later on.

20. Derek Jeter, 2010: Three Years, $51 million

Jeter gets the edge over Posada here because of the AAV tiebreaker.

This was the winter where Jeter leaving the Yankees seemed as real as it ever became. This contract comes from the period chronicled in "The Captain" where Brian Cashman reportedly responded to Jeter's request to learn "who he'd rather have" at short by talking up Troy Tulowitzki.

It created bad blood, but the job got done. It always did.

19. Johnny Damon, 2005/Chase Headley, 2015: Four Years, $52 Million

Before "Aaron Hicks is the Left Fielder," there was "Bubba Crosby is Our Center Fielder."

That's just about the time when Brian Cashman pulled off the biggest heel turn in the history of the Yankees-Red Sox rivalry, heisting Damon after Boston's failed follow-up to the 2004 title in October 2005.

Damon went on to match seemingly impossible expectations for agitation in the Bronx after shaving his trademark "Idiot" beard, never making an All-Star team with the Bombers, but piling up two of the three best offensive seasons of his career and swiping two bases on a single play to help punch the Yankees' ticket to their 27th World Championship. Worth it. Better than Bubba.

As for Headley? Eh. The Yankees don't really make midseason trades they don't intend to extend (sorry, Andrew Benintendi), and Headley was perfectly average for three seasons/in San Diego for Year 4 of this deal.

Mostly forgettable, except when he flopped on the base paths in the 2017 ALCS against Houston.

18. Jorge Posada, 2007: Four Years, $52.4 Million

This legacy contract carried Posada to the end of his Yankees career, when he walked away after the 2011 season as a catcher/DH, sinking below the league average in OPS for the first time since 1999.

How Posada hasn't gotten more Hall of Fame consideration is stunning -- oh, wait, no it's not. He got automatically dinged by the voters for being a Yankee. Never mind, not stunning. Normal.

This contract, alongside Jeter's, Mo's, and a number of one-year deals for Andy Pettitte, helped keep the core together for one more title run in 2009 -- a season where Posada turned back the clock and hit .285 with 22 bombs and a 125 OPS+ as a 38-year-old.

17. Hideki Matsui, 2005: Four Years, $52.5 Million

After a successful first contract in the Bronx, the Yankees brought Matsui back for more after the 2005 season -- and don't win the 2009 World Series without him, either.

His Yankee career probably (sadly) ended at the exact right time, riding a significant high into the aging curve in Anaheim.

Matsui wasn't a 50-homer slugger in New York like he was with the Yomiuri Giants, but he was a stunning natural hitter, and quite possibly the "clutchest" Yankee of the decade, as unquantifiable as that title is. In 2009, he hit .303 with 8 homers and 65 RBI with RISP and .240 with 15 solo bombs with the bases empty. During that year's World Series, he wrapped his time in the Bronx by hitting .615 with three homers, despite being unable to DH and start on the road in Philly.

All-time Yankee.

16. AJ Burnett, 2009: Five Years, $82.5 Million

Another Yankee without whom -- say it with us, now -- they don't win the 2009 World Series. Not worth the money, but simultaneously worth it all and then some.

Burnett came guns blazing from the Blue Jays, a surprise addition in the wake of CC Sabathia joining the Yankees. He helped front a surprisingly thin rotation for the Yanks in '09, throwing 207 innings, striking out 195 and leading the league with 97 walks. It was almost an exact replica of what he'd done the season before in Toronto (no notes): 18-10, 4.07, 231 Ks in 221.1 innings pitched.

He's best known for Game 2 of the '09 World Series when he limited Philly to four hits and one run in seven innings, striking out nine and walking two -- and don't forget when he held the Detroit Tigers down in an elimination Game 4 of the 2011 ALDS, bouncing back for a big game after his regular season had gone off the rails.

The Yankees sold Burnett at his lowest after '11, and he bounced back in full with the Pirates, making his first and only career All-Star team in his final season in 2015. A career well-lived.

15. Brian McCann, 2013: Five Years, $85 Million

Probably the ghastliest deal on this list, if not for that other, slightly more ghastly deal ... and that other one that's also worse ... yeah, the Yankees have full-scale beefed it a couple times recently, haven't they?

McCann was supposed to be the Captain of the Unwritten Rules of the Yankees' mid-2010s spending spree, and though he ripped 20 homers per season in the Bronx and somehow finished 24th in the MVP voting in 2015 (26 bombs, 94 RBI, .232 average), he was well below his peak, ranking as a league-average offensive player the entire time.

Anecdotally, he also had a propensity for popups to the right side of the infield. The McCann experience was no fun -- just the way he likes it.

Naturally, he ended up on the 2017 Astros and delivered some big blows at the tail end of the ALCS. Why wouldn't he have done that? Had to see that coming. Just like McCann's teammates.

14. Aroldis Chapman, 2016: Five Years, $86 Million

The Yankees pulled off their favorite gambit when they traded for Aroldis Chapman at a discount following the 2015 season (as he dealt with a pending domestic violence suspension), traded him at the 2016 deadline to the Cubs and secured Gleyber Torres, then re-signed him to a mega-deal in the offseason.

Wow! What a lose-lose!

Chapman had an option to depart after 2019, but somehow, the Yankees further extended this contract and kept him around for an additional three seasons and $48 million. Cool.

13. Bernie Williams, 1998: Seven Years, $87.5 Million

Yes, the Yankees almost lost Bernie Williams to the Red Sox back in 1998-99 before relenting to their center fielder's demands and keeping the band together. That was a wise move!

Williams delivered, upping his league-leading .339 average to .342 the next season, a year that coincidentally featured the Yankees and Red Sox facing off in the ALDS.

Bernie Went Boom to set the tone in that series, delivering a walk-off home run off Rod Beck in Game 1 at Yankee Stadium that never would've happened if Steinbrenner hadn't ponied up over the previous winter.

For an accomplished guitarist, it was one hell of a solo ... shot.

12. Mike Mussina, 2001: Six Years, $88.5 Million

Mike Mussina somehow managed to pitch well for the Yankees, embellish his Hall of Fame career, and never win a World Series with the team.

He joined the Bombers as the coup of the 2000-01 offseason, flashing his old stuff in both 2001 (143 ERA+) and 2003 (130 ERA+), but mixing a few fringe-average seasons in there as the team struggled to recapture their dynastic glory in October.

His signature Yankee moment came in relief in Game 7 of the 2003 ALCS, when he held the fort in an entirely unfamiliar situation, allowing the Yankees to ultimately rally against Pedro Martinez and Grady Little's idiocy.

Over eight years in the Bronx, he won 20 games once: his final season, 2008.

11. DJ LeMahieu: Six Years, $90 Million

The jury's out on this one until the Yankees get a clean bill of health on LeMahieu's toe, but when he re-signed after the 2020 season, he went from one of the biggest bargains in Brian Cashman's recent history to a mid-tier question mark.

When LeMahieu's been healthy and available, he's delivered consistently and brought a much-needed gap-to-gap element to this home run happy team.

His season with the juiced ball in 2019 was ridiculously fruitful (26 bombs, .893 OPS, 136 OPS+), but his 2020 was somehow even stupider (1.011 OPS, 178 OPS+, .364 average in 50 games).

Don't let the uncertainty fool you, though; LeMahieu still registered 3.8 WAR last year despite being dragged down significantly during his final month of action, where he couldn't pivot or strike the ball with any pop.

10. Jason Giambi: Seven Years, $120 Million

Giambi's Yankees tenure is widely remembered as disappointing, but ... why? He did exactly what he was asked -- and, like Mussina, somehow deftly avoiding winning rings here.

Still, you want incredible regular seasons? Giambi hit 41 bombs, knocked in 122 runs, and finished fifth in the MVP voting his first year in the Bronx in 2002. The next year? 41 blasts again, alongside a league-leading 129 walks.

His 2004 season was marred by a strange parasitic infection, and he got injured in 2007, too, when his career was closer to the end. But 2005-06 were two more classic Giambi seasons (led the league in OBP in '05, socked 32 and 37 bombs). He also hit in October, smashing three homers (two in Game 7 off Pedro) against the Red Sox in the 2003 ALCS, then hit .421 in New York's ALDS failure in 2005.

Good Yankee. Would be more appreciated in the modern era, which sounds insane to say about someone who played in New York from 2002-2008. His strikeouts would be shrugged at these days, though.

9. Jacoby Ellsbury: Seven Years, $153 Million

What is there to say about this? Do we have to say anything about this? What is there to say about Jacoby Ellsbury that has yet to be said?

He was solid for the 2014 Yankees after defecting from Boston and pulling a proto-Damon, but he was borderline unplayable (and rarely healthy) offensively from 2015-17, then was eventually sent into the void, as the Yanks worked tirelessly to prove he never existed in the first place.

Sadly, this figment of imagination took them to court when they took him to task over consulting an outside doctor, only to reemerge when it was time to honor Dustin Pedroia at Fenway. Insipid 'til the end.

8. Masahiro Tanaka: Seven Years, $155 Million

Masahiro Tanaka's offseason contract, which capped the Ellsbury/McCann/Beltrán ill-fated spending spree, has universal approval to this day.

Though Masa suffered a partial UCL tear during his dominant first season in the Bronx, the injury ultimately never required Tommy John surgery, and he remained healthy long enough to become a postseason legend in 2017 and 2019.

His playoff reputation was only pricked once with fans in the stands -- on short rest by the 2019 Astros in Game 4 of the ALCS, a few days after his greatest masterpiece, a Game 1 six-inning one-hit shutout.

Unfortunately, he was rocked twice in the 2020 postseason (once when a rain delay interrupted his start in Cleveland), and has pitched in Japan the past two seasons. Not as dominant a regular-season Yankee as once was forecast, but objectively a good buy (especially considering his offseason still has the Ellsbury stink on it).

7. CC Sabathia: Seven Years, $161 Million

The crown jewel of the 2008-09 offseason, and the pitcher the Yankees had to have.

He did everything asked of him and more from 2009-2012, throwing 230+ innings from '09-'11 and winning a title as the ace of a three-man staff in his first season in the Bronx. Glad he decided he preferred the cold weather and pressure in New York to a long-term California home.

Eventually, Sabathia battled sobriety and struggled as he aged, but pulled things together spectacularly to post a second exceptional run with the team from 2016-19, serving as the veteran leader on a staff of newcomers (and passing the 3,000 strikeout plateau).

He's destined for Cooperstown. The only issue is exactly how many fools hold his 3.74 ERA against him and how long we'll have to wait.

And now, for a player the Yankees hope will eventually pick a thing or two up from Sabathia...

6. Carlos Rodón: Six Years, $162.5 Million

Welcome to New York, Carlos Rodón! The bulldog left-hander just parlayed back-to-back years of his life into a dream gig with the Yankees, and came down from his highest asking price to get it done.

Rodón's Yankees story has yet to be written, but it seems like he has the perfect combination of stuff and mentality to slot in directly behind Gerrit Cole and intimidate teams into realizing there aren't any breaks coming in a short series.

Last season, Rodón struck out 237 men in 178 innings. More of that.

4. Honorable Mention: Derek Jeter: 10 Years, $189 Million

Technically signed one year prior to Jeter hitting free agency, the Yankees locked up their future Captain before the 2001 season, ending any drama for the next decade.

After this deal was signed, the only uncertainty remaining was, "How many celebratory Jello Shots could Jeter down, and where?"

Any time you can lock down an icon before he makes it to market, that decision's probably wise. Not a free agent deal, but still the fourth-richest contract this team has ever signed, meaning -- against all odds -- there are only three $200 million-plus contracts of any kind on this franchise's books all time.

3. Alex Rodriguez: 10 Years, $275 Million

Alex Rodriguez got exactly what he wanted when he and Scott Boras upstaged the Boston Red Sox run to the 2007 title, announcing he was opting out of his Yankees contract midway through the Fall Classic.

Conventional wisdom probably told the Yankees to run away here, but they didn't do things conventionally at the end of George Steinbrenner's reign. Instead, the Bombers signed Rodriguez to a 10-year, $275 million deal ... that ultimately didn't net them 10 years of production.

PROS: Literally don't win the 2009 World Series without him. This doesn't have to be a thought exercise. He was EVERYWHERE that postseason.

CONS: 2009 steroid drama, 2013-14 suspension, strange phasing out in 2016.

All in all, you have to do it again if you want that ring, still the most recent hardware this team has earned and the franchise's only post-Subway Series title.

2. Gerrit Cole: Nine Years, $324 Million

For every fan who wants to give out $300 million deals to Marcus Semien and Corey Seager like chiclets, keep in mind that Gerrit Cole was this franchise's first -- though, as contract figures throughout the league continue to rise, it'll someday be dwarfed by a free agent deal for, like, Jackson Holliday.

Cole has been an ace since signing in New York, no matter what MLB Network says, and put some of his postseason bugaboos to bed when he put the Guardians to sleep last fall. Huh. Maybe pitching at Fenway Park on a bum hamstring isn't the be all, end all?

Still, this contract will be criticized (rightfully so) if the gopher balls continue to rise, and if Cole's unable to reach the World Series and triumph. The Yankees outbid the field significantly to get their man, a Yankee Fan Today, Tomorrow, Forever. This city that never sleeps won't rest until he's on top of the world.

1. Aaron Judge: Nine Years, $360 Million

Bet on yourself. Earn $360 million. Listen to Hal Steinbrenner grovel from Italy before you sign the contract. Make the Yankee family squirm by talking to the Giants and Padres for a little too long. Commit arson. Gain the captaincy.

Aaron Judge, you did it. AL home run record. Largest deal in Yankees history. Now comes the hard part.