Yankees: 3 missed opportunities that doomed NYY for 2021

2. Signing Michael Brantley to 3-Year Deal After 2018

The Yankees not signing Michael Brantley will haunt us.

In 2021, the Yankees’ outfield picture is nearly settled, with Clint Frazier poised for regular at-bats when the season begins.

But in 2018 and 2019, the Yanks worked hard to deny Frazier such at-bats at every turn. And in ’19, Frazier was truly a last resort following his early season fielding blunders, as the entire outfield succumbed to mass casualties.

You know who might’ve helped provide both a lefty change-of-pace in the batting order, improved on the Brett Gardner spot, and allowed the Yankees to weather their outfield injury storm in ’19? Michael Brantley, who instead went to the team that whipped the Bombers out of the playoffs yet again that October.

This is crazy (it’s not that crazy) but even in 2021, Brantley would be helpful, especially as it looks more and more like the regressing Gardner could be a budget casualty. After all, it’s nice to have additional good players! If your roster depth is actually good, injuries would be less of a catastrophe — less of, say, an invitation for Shane Peterson to show up, which is something that actually happened in 2018 when the Yanks didn’t have someone like Brantley.

It’s clear by now, though, that adding Brantley in 2021 would only confuse things, and — like a Charlie Morton addition — would be too little, too late. Mark my words, though: The Yankees would have a 2019 World Series ring (or at least an American League title) if the Brantley had been on the other foot.