15 free agent (and trade) near-misses that would've changed Yankees history

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Starling Marte/Robbie Ray Trades, 2020 MLB Trade Deadline

At the time, this seemed like a fairly obvious outfield upgrade for a Yankees team that entered 2020 as a prohibitive favorite, only for the year to go completely off the rails with a pandemic no one could've forseen the day Gerrit Cole signed on the dotted line.

Conversely, Robbie Ray felt like a poor Cashman decision in the making; the high-strikeout, high-walk, high-struggle left-hander seemed likely to be dealt for more than his worth. Projections had the Yankees ending up with both players.

Marte went to the playoff-bound (!!!) Marlins and actually struggled down the stretch (86 OPS+), but in the tiniest 28-game sample size that could've easily reversed itself in October, when the Yankees relied heavily on Brett Gardner instead. Ray went 1-1 with a 4.79 ERA, but could've changed the path of the 2021 season, winning the Cy Young in Toronto over Gerrit Cole.

The Yankees notably stood pat at this deadline, a plan that unraveled when Deivi Garcia/JA Happ combined to start a playoff game while their offense couldn't touch the Rays.