Yankees: 4 best deals in MLB Winter Meetings history

The New York Yankees have done plenty of big spending and wheeling and dealing at the MLB Winter Meetings over the years. These four deals best stand the test of time.

If an agent worth their salt wants to make sure they have a competitive market for their client during the MLB Winter Meetings, they’d better hope the Yankees have shown a willingness to spend in recent days.

For better or worse, the Yanks are usually involved in high-profile negotiations this time of year, either as a Scott Boras marketing ploy, or out of genuine interest.

Most Winter Meetings, the team is on the verge of contention, and Brian Cashman is at least authorized to do something of note, whether it’s a shrewd trade or the presentation of a blank check to the team’s desired target.

Sadly, we’re missing out on the glitz and glamor of the Winter Meetings this year, which have gone entirely virtual (good call!). It’s likely some big decisions will still be made Dec. 7-10, though this offseason is unlike any other in more ways than one. The non-tender deadline hasn’t been quite as bleak as we thought it would be in this landscape, but if a guy like Eddie Rosario can be outright cut by the Minnesota Twins, it’s safe to assume this won’t be a hotbed of your typical blockbusters.

With that in mind, let’s look back at the Yankees’ greatest successes during this fateful December weekend. After all, success is better than inaction or failure!

Yankees Honorable Mentions:

2009: Three-Way Trade Involving Curtis Granderson to NYY

1984: Rickey Henderson to the Bronx

More Articles About the Best of the Yankees:

4. Gerrit Cole Signs Record-Setting Deal, 2019

The Yankees nabbed a franchise-changer when they signed Gerrit Cole.

It would be unfair to place the Gerrit Cole signing any higher, at this point, considering we’ve only seen one 60-game sample of his many talents.

But after several years of missing a significant piece and operating without a clear take-charge ace atop their rotation, the Yankees refused to sit idly by in 2019, signing Cole to a nine-year, $324 million deal that they had apparently been concocting for years, wining and dining him with his very specific favorite vino.

It’s the little details, you know?

Cole’s first season in the Bronx did not look the way either side intended it to, but when September rolled around — fanless, unfortunately — he still took charge of the stretch run. He finished the year 7-3 with a 2.84 ERA, along with 94 strikeouts in 73 innings, good enough for fourth in the AL Cy Young balloting. His playoff debut with New York was sterling; out of seven total postseason games, Cole pitched three of them, and his seven-inning, two-run, 13-strikeout opener against the Indians’ Shane Bieber was what Winter Meetings dreams are made of.

Though the Yankees would’ve preferred to win his short-rest Game 5 against the Rays in San Diego, Cole surrendered just a single hit and struck out nine in 5.2 must-win innings.

With eight more years of this Winter Meetings masterstroke to go, the Yankees are still quite satisfied.