At the time, I wrote that the trade could play out in one of three ways. Last season, Paxton started slowly but finished strong, but the Yankees didn't win. Meanwhile, Sheffield didn't look good at all in 2019. Scenario #2, a wash for both teams, played out in Year One.
Year Two, which also happens to be Paxton's last season under contract, is nearly in the books. Paxton took a step back, battling health issues and making only 5 mostly unimpressive starts. It remains to be seen if the Yankees will win a title this year. Less likely will be Paxton making a significant contribution to that title run.
Meanwhile, something funny happened in Seattle. The Mariners made an unexpected push towards the playoffs. Leading that charge was a dominant Justus Sheffield. In September, Sheffield won his last 4 starts, averaging over 6 innings per start without giving up more than 2 runs. While only a small sample in a short season, those are looking like "ace" numbers.
Although no one could fault Cashman at the time for making a move -- it's what General Managers are paid to do -- hindsight is always 20/20. As with any trade, its success or failure may not be known for years. (Ask the guys who traded away John Smoltz or Jay Buhner.)
If the Yanks let Paxton walk after two seasons without a championship, his acquisition would be no more than a footnote had Sheffield continued to pitch as he had in 2019. But if Sheffield builds upon his 2020 breakout and continues his upward trajectory, this deal may not so easily fly under the radar anymore.