GettyYankees GM Brian Cashman

Brian Cashman has been the Yankees general manager for the last 26 years, and considering the organization’s history of volatility in that role, he probably does not have to worry about job security much, even with the Yankees’ sitting on a 15-year World Series championship drought, one of the longest in franchise history.

That championship drought has been a point of contention for Cashman, who has long insisted that the 2017 Yankees could well have won the World Series if they were not “cheated” (as he says) by the Houston Astros‘ sign-stealing scandal. Cashman has been openly hostile to all things Astros in the years since.

But would that preclude him from pursuing one of the most important cogs in that Houston title team, especially if that cog could be a perfect fit for the Yankees roster? That is an important question this winter as the Yankees prepare to reconfigure their infield, with third base coming in as a top priority.

That’s because the biggest free-agent third baseman available is Alex Bregman, who has spent all of his nine-year career as an anchor in the Astros lineup.

Alex Bregman an Ideal Fit at 3B

Bregman makes sense for the Yankees, assuming the plan is to move Jazz Chisholm to his more natural second-base spot. Chisholm was acquired in July, ahead of the MLB trade deadline, from the Marlins, and though he had ample experience as a second baseman, had not played third before. But he held up at the position for the stretch run, even if only temporarily.

The Yankees are likely to let free-agent second baseman Gleyber Torres walk this winter and move Chisholm back to second base, leaving a gaping hole at third. Bregman, who hit 26 homers and batted .260 this season, could be ideal.

While Bregman won’t be cheap and the Yankees’ priority will be keeping outfielder Juan Soto in place, his projected contract at Spotrac–four years, $120 million–is not out of the Yankees’ range, especially if the team uses cost-effective prospects like Jasson Dominguez, Spencer Jones and/or Ben Rice going forward.

Yankees’ Brian Cashman Still Resents the Astros

But then, there is the whole Astros-cheating connection, and Cashman’s disdain for Houstonians.

Writes MLB Trade Rumors’ Anthony Franco

“Alex Bregman is the only star third baseman available in free agency. He’s a strong fit for the roster on paper, but a pursuit could be clouded by the Astros’ sign-stealing scandal. Cashman has continued to take shots at the 2017 Houston team that beat the Yankees in the ALCS, doing so as recently as last week. “I hate the 15-year (pennant drought) because it completely forgets and discounts that some other organization cheated us. … I think we would’ve been advancing,” the GM said in an appearance on MLB Network’s High Heat.

“It’s fair to assume a large portion of the fanbase feels similarly. While that doesn’t inherently mean the Yankees won’t consider Bregman, it’s a complicating factor.”