Yankees: These two biggest free agency mistakes cost NYY a World Series

If the Yankees had signed these two players — or even one of them — they probably win a World Series.

The New York Yankees very well knew their deficiencies following the 2018 season. They needed another reliable starter. They needed another productive left-handed bat. Lance Lynn and Sonny Gray weren’t working out. Greg Bird was downright bad (and injured). Neil Walker was hitting free agency. Didi Gregorius had only one year left before he hit the open market.

After getting clowned by the Boston Red Sox in the ALDS, you’d think general manager Brian Cashman would make momentous moves to get immediate revenge in 2019. Though the additions of DJ LeMahieu, James Paxton, JA Happ, Adam Ottavino and Zack Britton were considerable, only two of those ended up working out over the last two years.

The Yankees overlooked two of the most consistent and under-the-radar options in free agency that offseason: Michael Brantley and Charlie Morton.

Now, it’s too late. Perhaps making a run at one of them this offseason (they’re both set to be free agents) could help, but instead of giving JA Happ $16 million per season and Adam Ottavino $9 million per season, that money could’ve been invested to sign both Brantley and Morton, both of whom were scooped up by the Yankees’ rivals. Brantley signed with the Astros on a two-year, $32 million deal and Morton landed in Tampa on a two-year, $30 million deal.

Think the Yankees could’ve used both of those guys on short-term deals and at great rates? Brantley, a smooth-swinging lefty, hit .305 the past two seasons and would’ve been perfect for the short porch in right field. Morton, a veteran right-hander with tremendous movement and control, is quite literally unstoppable in winner-take-all postseason games.

On top of that, both of these guys actively played a role in ousting the Yankees from the postseason in 2019 and 2020. Morton shut down the Yanks across five innings of work in a pivotal ALDS game a little over a week ago while Brantley batted .304 in the 2019 ALCS.

But Cashman’s focus was elsewhere. He wanted to build an unstoppable bullpen. He added a starter via trade after dealing from a surplus in the farm system. He worked to retain Happ after his tremendous performance in the second half of 2018.

Still, these two were big misses and it’s clear the front office was lacking in their research because signing at least one of Brantley or Morton felt like a necessity for the Yanks.

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