Yankees: 4 best deals in MLB Winter Meetings history

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HOUSTON, TX – OCTOBER 13: CC Sabathia #52 of the New York Yankees warms up before game two of the American League Championship Series against the Houston Astros at Minute Maid Park on October 13, 2019 in Houston, Texas. (Photo by Tim Warner/Getty Images) /

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.