What’s the Biggest Contract the Yankees Ever Gave a Player?

No sports organization spends money quite like the New York Yankees. For decades, the Beasts in the Bronx assembled rosters packed with a bunch of other teams’ former fan-favorite players.

These days, the Yankees are uncharacteristically quiet on the free-agent front. The organization turned to the more cost-efficient tactic of developing players long-term, rather than buying up complete players at exorbitant rates — with a few exceptions.

One of these exceptions occurred this offseason. The Yankees handed down their biggest contract yet — at least, the biggest one they’re 100% responsible for.

Why Gerrit Cole beats Giancarlo Stanton for the biggest Yankees contract ever

If you simply scan the raw numbers, Giancarlo Stanton has the biggest Yankees contract, valued at $325 million. While the Yanks are on the hook for this massive sum, they simply inherited it from the Miami Marlins. That amount is spread over 13 years, which the Marlins began paying back in 2014.

This leaves the most recent player signed to the Bronx, former Houston Astros ace Gerrit Cole, as the biggest stack of cash the Yankees committed to yet. His nine-year, $324 million contract falls just a hair shy of Stanton’s total. It gives Cole a bigger payout per year.

Before this splashy acquisition, starting pitcher Masahiro Tanaka‘s arm earned him a cool $155 million in the Steinbrenner family’s books.

Taking on the remainder of Stanton’s contract was one thing. After a long run of snubbing the biggest free agents on the market, Cole’s signing that the Yankees are ready to be a big postseason threat by any means necessary.

Remember when Alex Rodriguez’s contract seemed insurmountable?

Alex Rodriguez is the perfect microcosm of the type of contract the Yankees were known for. The Mariners’ favorite broke hearts throughout Seattle when he signed a massive $252 million contract with the Rangers. That record-setting payout didn’t last long, however.

Rodriguez opted out and took an even bigger stack from NYC: $275 million. This contract seemed over the top at the time. It wasn’t helped by A-Rod’s slow start in the Bronx. Plus, he had a falling out with former close friend and fan-favorite shortstop Derek Jeter. This feud led to a persistent slow-roll of bad press about the team.

Overall, Rodriguez delivered. Except for his suspension for performance-enhancing drugs, the 14-time All-Star earned his pay despite controversy. But it may not be a coincidence that, in the wake of the A-Rod/Jeter era, the Yankees steered away from its classic free-agent-forward style.

How George Steinbrenner changed baseball by spending big

Before 1973, baseball contracts were relatively stabilized by a broad unwillingness to pay big. Curt Flood‘s fight for the right for players to choose which team to sign with sent salaries close to the level of revenue each player generated for owners.

But the real big contracts didn’t start flowing until after 1973 — when George Steinbrenner bought the New York Yankees. Steinbrenner took a far less conservative approach to signing players. He realized the potential of the team’s healthy revenue could only be bolstered by winning more and signing the most talked-about players he could get his hands on.

For decades, the Yankees laid out ever-larger contracts for some of the best players in baseball. Within a few years, the Reggie Jackson-led Yankees won back-to-back World Series titles.

This strategy hemorrhaged money in the short term while turning Steinbrenner’s $10 million investment in the team to a multi-billion dollar concern. This approach didn’t always work, especially as modern analytics opened the door for cheap pre-free agency players to turn savvy teams into postseason contenders.

Today, under George’s son Hal Steinbrenner, the Yankees are more measured about signings. When the opportunity came to bolster his young, talented team with a costly veteran ace, though? Hal seized it. And if Cole stays healthy, it should be worth the unbelievable amount of money he’s getting paid.