Yankees fans’ favorite left field option could be destined to join NYY past his prime

The year is 2022. The New York Yankees require a left-handed hitting complement to their big boppers in the outfield who can pound 15-20 homers, but also make consistent contact. The Yankees need someone who rarely strikes out and can hold their own defensively.

The Yankees need Michael Brantley, just as they did after the 2018 season, and just as they did after the 2020 season. Of course, they need him a little less now than they did during those previous two free agency cycles. After all, Brantley is 35 going on 36 and coming off a stint on the 60-Day IL with a shoulder issue. Nobody knows what version of Brantley will take the field on Opening Day, but he’s clearly less of a sure thing than he was in 2019, when he hit .311 with an .875 OPS in 148 games, or in 2021, when he hit .311 with a .799 OPS in 121 games.

Guess which version of Brantley has the best chance yet of landing on the Yankees.

The 2018-19 offseason, when they passed on him the first time and watched him greatly aid their newfound rivals instead, was the famous “we have six outfielders” offseason that led to Brian Cashman also passing on Bryce Harper. After 2020, what was the Yankees’ excuse, other than general apathy? It was obvious at that point that the roster was unbalanced, and Brett Gardner was closer to retirement than being an impact player.

And yet, the Yankees let him drift yet again, watching Houston nab him for a second go-round, which helped propel the Astros past the Red Sox, something New York could only dream of.

If Yankees sign Michael Brantley now, it’ll be too late

This offseason, the Yankees will need to fill a void in left (and, sadly, potentially also in right). They’ll likely aim to do so by securing the services of a left-handed hitter who can blend into the background, occasionally tagging a ball to the short porch, but mostly on a mission to slice singles and doubles into the gap.

Brantley fits that description, but he fit it better four years ago. 28-year-old Andrew Benintendi is the most likely option, but Brantley might be a better budgetary fit … again, because he’s beginning to break down. The sad reality is that any hitter who fit the 2019 Yankees like a glove will always be more likely to join the team three years later.

Oh, and there’s also that whole little thing where Brantley was nearly a member of the Blue Jays outfield in 2021 alongside George Springer before the deal dissolved in a cloud of confusion.

What happened there? Who knows. But if there’s even a chance Brantley’s still got it, the Yankees might balk at giving Toronto a second chance here.

Or, you know, they might not. Didn’t blink last time. Might not blink again.

Brantley and the Yankees have been a match made in heaven for several years, but a deal makes the least sense it ever has this offseason.

Benintendi would be a better fit. Michael Conforto, also hobbled, will be looking for a pillow contract; he could be cheap and effective and younger. A Bryan Reynolds trade would be the power move. A Brantley signing would represent playing catch-up, winded after a four-year sprint to finally reach a predictable destination.

Could be worse, though. Gardner’s still out of a job, too.

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