Yankees’ reason for missing Manny Machado trade in 2018 will shatter you


Though there’s more than a dose of optimism about the 2022 Yankees‘ season to date, as well as their deadline fate with a chance to get over the hump, Padres superstar Manny Machado dropped a downer on the Bombers’ faithful over the All-Star break.

On the bright side? Through the fallacy of the predetermined outcome, Yankees fans can now convince themselves they missed out on the most controversial half of Machado’s career coming in pinstripes. So … so that’s something.

According to the Padres’ 30-year-old superstar, he was very nearly traded in-division from the Baltimore Orioles to the Yankees back in 2018 at the trade deadline, and believed the deal was done before some wires got crossed.

Ultimately, Machado headed west to join the Los Angeles Dodgers, where he did participate in the 2018 World Series, but also stomped on a few Milwaukee Brewers’ appendages to get there, fended off some hustling questions, and made the last out of the series from his behind, screwed into the ground by Chris Sale. There’s no doubt that some of that controversy led to the Yankees staying all quiet on the western front when Machado hit free agency days later — well, the controversy, and also the Gerrit Cole contract they were planning on for the next winter.

Still, though, it would’ve been nice having Machado for an equivalent package to the one the Dodgers surrendered back in 2018, highlighted by righty Dean Kremer and a few top prospects who’ve yet to pan out. The ALDS with the Red Sox might’ve been a bit more fiery with a great antagonist in place (besides Aaron Judge’s boombox). Alas, the deal got spiked because the Yankees reportedly wouldn’t include … Justus Sheffield?

Yankees lost Manny Machado trade because of Justus Sheffield

As Machado put it bluntly:

"“I thought I was going there [to New York],” Machado told reporters Monday in Los Angeles, according to NJ.com. “I guess the trade didn’t go through and I went to the Dodgers. I don’t really know the full story, but I thought I was going there [to the Yankees].“Me and New York go back a long time,” Machado said. “I played there (for Baltimore) and fans always showed me love. It’s a special place. … I thought I was going there and then it didn’t happen.”"

While the reasoning for the deal falling apart was largely lost to history — and no one, at the time, knew quite how “done” things were, the Orioles’ interest in Sheffield was very well advertised that summer.

Sadly, it seems this was more than just an idle ask embedded in a long conversation; a very close deal hinged on Sheffield, and the Yanks didn’t pay up.

Ultimately, the Yankees didn’t deal Sheffield for a “rental,” but rather for two years of James Paxton, which turned into a great half-season and some injury-plagued months along the way.

Machado in 2018, setting the stage for a contract extension the Yankees might grouse about but could certainly afford, would’ve been a better use of resources.