I Admire Cashman For Building A Better Team, But This One I'm Not Feeling

Let’s get this out of the way upfront: I’m not a huge fan of the idea of Alex Bregman joining the Yankees. Yes, the guy has been a Yankee killer for years, and yes, it would be poetic justice to have him hammering homers for us instead of against us. But the idea of Bregman—an Astro through and through—putting on the pinstripes just doesn’t sit right with me. That being said, I’ve got to hand it to Brian Cashman: he’s out here playing chess, not checkers, and his determination to upgrade this team has my full respect.

Let’s talk about what’s happening. Houston is stumbling when it comes to keeping Bregman around. They’ve offered him a massive six-year, $156 million deal—the largest in team history—but so far, no dice. Meanwhile, the Astros already dealt Kyle Tucker to the Cubs, and now the Yankees have entered the conversation, sniffing around for a bat to juice their offense.

Bregman’s numbers are solid. Sure, he got off to a slow start in 2024, but when it mattered most, he delivered—because that’s what Bregman does. He’s a consistent offensive force, a defensive stalwart at third, and a player who knows how to win. He’s the kind of guy who thrives in high-pressure situations.

So, why am I hesitant? It’s not his talent; it’s his baggage. Bregman was the face of the 2017 Astros—the team that cheated its way to a World Series. While some fans are willing to overlook that for the sake of winning, I’m not sure I can stomach seeing him celebrated in Yankee Stadium, a place built on tradition, integrity, and (mostly) clean victories.

Now, let’s shift to Cashman. I’ll admit, he’s taken his fair share of criticism in recent years—and I’ve been one of those critics. But right now, I have to tip my cap to him. Cashman is clearly on a mission this offseason, and he’s leaving no stone unturned in his quest to make the Yankees better.

“[Bregman’s] been a thorn in our side for years,” Cashman said recently. “Good players like him make a lot of money. I’ve had a conversation or two with Scott Boras with a lot of his clients, including Alex Bregman.” That’s the kind of aggressive mindset we need from the front office. Whether it’s Bregman, another slugger, or a sneaky under-the-radar move, Cashman’s eagerness to improve this team is refreshing—and it’s exactly what the Yankees need after falling short in 2024.

If the Yankees don’t land Bregman, he’s got other suitors. The Red Sox are hot on his trail, with manager Alex Cora and team president Sam Kennedy reportedly big fans. But Boston’s front office isn’t unanimous in its love for Bregman, which could create an opening for the Yankees to swoop in.

Detroit is also in the mix, but let’s be real—Detroit isn’t exactly the dream destination for a guy like Bregman. New York or Boston would clearly be the more appealing options, assuming the money’s right.

As much as I respect Cashman for exploring every avenue, I’m still not sold on the idea of Alex Bregman in pinstripes and it’s definitely because of Cheat Gate.

That said, if Cashman pulls the trigger and brings Bregman to the Bronx, I’ll support the team like I always do. Winning cures a lot of ills, and who knows? Maybe Bregman, with his proven track record and big-game mentality, will win me over. Until then, I’m cautiously skeptical—but grateful that Cashman is doing everything in his power to get us back on top.