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When the Yankees went through their mini-teardown in 2016, their top trade chip was Andrew Miller. With his contract stretching through 2018, New York had significant leverage and could have held onto him into the offseason.

In the end, as you likely know, they dealt him at the deadline to Cleveland for Clint Frazier, Justus Sheffield, Ben Heller and J.P. Feyereisen. Heller and Feyereisen are just relievers (and still in the system) while Frazier and Sheffield were the big names. Frazier has played a big role on the 2019 roster while trading Sheffield produced James Paxton. Considering how prospects go awry, that’s a pretty good haul.

But the Yankees could have had a 2019 Cy Young favorite.

That’s right. According to the report at the time, the Yankees could have acquired Lucas Giolito straight up for Miller. That offseason, the right-hander would be dealt to the White Sox in a package for Adam Eaton. The same pitcher who just shut down the Yankees last weekend. Wouldn’t the 6-foot-6 Giolito fit in perfectly with the rest of New York’s goliaths?

This season, Giolito leads the American League in wins and complete games and is in the top seven in both ERA and FIP. He’s sixth in baseball with 3.0 bWAR and fourth among AL pitchers. Meanwhile, Paxton and Frazier have combined for 1.0 bWAR.


So the Yankees could have done even better with the Miller trade?

There are a few keys to remember. First, in any prospect trade, having more bites at the apple is key. Going for Giolito straight up would have been bold and likely unwise to bet your chips on young pitcher who’d already undergone Tommy John surgery. Getting a package of potential players from Cleveland, including two high-end prospects, was a safer bet.

Perhaps Brian Cashman could have extracted more from Washington. While this one-for-one deal was reported, we don’t know if it was actually on the table or if talks could have been expanded. Surely, the Nationals wish they’d gone all-in to get the reliever that could have put them over the top in 2016.

But, more importantly, Giolito didn’t progress in a straight line from where he was in 2016 to where he is today. He still needed most of a season in the Minors in 2017 and was the worst qualified starting pitcher in baseball in 2018.

The Yankees wouldn’t have been able to allow Giolito to flounder as he did in 2018. Kudos to the White Sox for taking advantage of their rebuild and giving Giolito the opportunity to get reps at the Major League level even as he struggled. Yet, there’s no way the Yankees, whose rebuild lasted just two weeks, could have stuck Giolito in the rotation for 30 starts last year while competing for the postseason, particularly if Sonny Gray were in the same rotation.

And does Giolito even make the same leap from scrub to star in the Bronx? Maybe. Much of his sudden improvement came from work he did on his own after last year, using weighted balls and changing his throwing motion. That could have happened with the Yankees, which has more player development staff under contract.

But it very well may not have happened. Giolito could have been shuttled to the bullpen or to Scranton Wilkes-Barre and ended up losing his confidence. The Yankees have had success developing pitchers — Luis Severino and Jordan Montgomery come to mind — but no team has perfect system.

It’s easy to dream about what Giolito could have done in pinstripes. However, when you get that in your head, you have to also picture how poorly his tenure may have ended. His 2018 season was worse than Gray’s horrid campaign, and that’s saying something. Giolito’s fortitude would have been tested if he had similar struggles in the Bronx.

Therefore, it’s hard not to realistically think of the Miller trade that happened as the best case scenario. Sure, there’s a universe where Giolito dons pinstripes and becomes the Yankees’ next great ace. But I’d bet those alternate timelines are more sparse than you think.