In baseball, timing is everything—especially when your agent moonlights as a press secretary. Scott Boras isn’t just selling Alex Bregman’s bat; he’s pitching fairy tales to front offices. The Boston Red Sox, already bruised by fan backlash and offensive anemia, now find themselves the latest target in Boras’ charm offensive. And if they blink too soon, they may end up paying for more than just Bregman’s highlight reel.
I think most of us don’t like Boras because he inflates the market, but if we were players, we would want him as our agent because he knows how to get you the big bucks. That is exactly what he is doing with Bregman and the Red Sox. With the third baseman searching for a long-term contract, Boras is back to playing the game that people don’t like him for.
One of the people who don’t like him is David Samson, and he is making his feelings clear again. In his recent episode of Nothing Personal with David Samson, he reacted to Boras hyping the Bregman deal. He said, “The agent comes out and says, ‘I just want you to know that Player X is so happy with his new team… He loves it there.’ I can’t even say it with a straight face, it’s so stupid… Scott Boras wants Alex Bregman to get a long-term deal because he didn’t get it from Boston.”
Bregman signed a short-term “pillow deal” with Boston—one year, opt-out included. It’s baseball’s version of speed dating: prove your worth fast or move along. The Red Sox needed a bat; Bregman needed a stage. It worked—until injury dimmed the spotlight just one month in.
Now, Scott Boras is dialing up the drama with classic PR playbook flair. “He loves Boston,” they say, as if that seals contract extensions. But this isn’t about love; it’s leverage wrapped in Fenway-flavored sentiment. Boras knows the Sox are bleeding offense and public goodwill—timing is everything.
In a conversation with Tim Healy of The Boston Globe, Boras explained that he always made it clear—at Bregman’s direction—that the door for negotiation has been open.“We’re always open to any conversation,” Boras emphasized, making it clear that dialogue with the Red Sox has never been off the table. Will Boston blink? Maybe. But not if Bregman stays shelved much longer. Without a long-term deal, odds are he walks—opt-out in hand and suitcase ready. Loyalty’s nice, but a clean bill of health and a bidding war speak louder.
Boras is playing chess while everyone else is still arguing over the checkers board. And with Boston’s front office juggling fan fury and lineup holes, the timing couldn’t be juicier. If Bregman cashes in despite the limp, Boras wins again—like he always does. But if the Red Sox bite too soon, they’re not buying a third baseman—they’re buying the sales pitch. Caution: fairy tales don’t come with injury insurance.
Alex Bregman might move to the Yankees
With Bregman caught in his latest chapter of high-stakes theater, even the Yankees are pulling up a front-row seat. The Red Sox might’ve thought they’d won a power bat; instead, they may have leased a headline. And if Boras has his way, Boston’s loss could be Bronx gold—just don’t expect anyone to admit it yet.
The Yankees don’t need another gamble—they need a glove, a bat, and October nerves. Bregman checks all three boxes, and then some. He brings postseason pedigree and a right-handed bat to a lineup leaning left. If the Yankees want to end their October silence, Bregman’s swing might just be the microphone. Of course, Bregman won’t come cheap—not with Boras holding the calculator. The Red Sox would demand elite prospects, maybe a major league-ready name. But for the Yankees, flags fly forever, and Bregman wears rings, not just wristbands. He’d cost a fortune, but missing the playoffs costs more.
If the impossible happens and Boston picks up the phone, the Bronx should shout back. Bregman in pinstripes would be pure baseball blasphemy—and pure postseason drama. Forget rivalry etiquette; this is war disguised as a trade. And if Cashman pulls it off, it might be his loudest win since 2009.
Baseball purists may clutch their pearls, but flags don’t care about front office friendships. If the Yankees want October thunder, they need to stop whispering around Boston and start dialing. Bregman wouldn’t just fill a hole—he’d light a fuse. And if Boras wants to burn bridges for a payday, the Yankees might as well hand him a match. After all, dynasties aren’t built on politeness—they’re built on power moves.
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