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.

2. Yankees Trade for Dave Winfield

The Yankees pulled off a coup when they brought Hall of Fame outfielder Dave Winfield from San Diego to the Bronx.

Looking at Dave Winfield, it’s no wonder the monstrous outfielder was originally drafted out of Minnesota by both NFL and NBA teams.

A borderline tight end in right field, Winfield had a rifle for an arm and a penchant for the long ball, cranking 37 home runs in his first full season in the boogie down in 1982 (thanks so much, 1981 strike!).

Winfield inked a remarkable 10-year, $16 million contract following the 1980 season, just a few days after the Mets (!) had raised the bidding to $1.5 million annually and the Indians had also tried to pry the 29-year-old away from San Diego. No dice — George Steinbrenner usually prevailed in those days.

Winfield never won a ring in the Bronx, unfortunately, only playing in one postseason in his very first year in pinstripes and hitting .045 in the World Series against the Dodgers, leading to the ignominious nickname “Mr. May” courtesy of Big Stein.

All in all, though, you don’t turn down a Hall of Famer when you see one; Winfield collected a ring with the 1992 Blue Jays anyway. Even Steven.

1. CC Sabathia

The Yankees guaranteed themselves a ring the second they signed CC Sabathia following the 2008 season.

It’s not supposed to be this easy.

Struggle for the first time in 13 years, sign the free agent ace who blew up the 2008 pennant race all on his own, and cascade down the Canyon of Heroes with the ’09 title? Yeah, we can work with that.

Sure, it would’ve been nice to win more than one ring with CC Sabathia in the Bronx, but the lefty was the consummate teammate throughout his entire 11-year tenure, replete with his own personal struggles which he never let bleed into the field of play.

Sabathia’s first four years were dominant (19-8, 3.37; 21-7, 3.18; 19-8, 3.00; 15-6, 3.38), and he was a postseason powerhouse during that stretch, commandeering the three-man Yankees rotation during the ’09 run and clinching the 2012 ALDS all by himself against the pesky O’s.

Sabathia earned a seven-year, $163 million deal from the Yanks following the ’08 season that set the tone for a blustery offseason, with the additions of AJ Burnett and Mark Teixeira soon to come. Brian Cashman reportedly got wind of Sabathia’s interest in his proposal and jet-setted from Las Vegas (the site of the Meetings) to Vallejo in order to secure the lefty’s services. The rest is history.

Sometimes it pays to get crafty and go off script, after all.

Yankees: 3 free agents NYY must avoid this offseason

The New York Yankees are going to have to get creative in free agency, and these three specific maneuvers should be very much avoided.