But let’s be real—this hurts in two ways. Toronto, already stacking their roster, just got stronger as a direct rival. On the flip side, it probably knocks the Jays out of the Bregman sweepstakes, leaving one fewer team for Boston to battle.

World Baseball Classic Semifinals: Mexico v Japan
Even if the Red Sox’s pursuit of Okamoto was genuine, it was always a pipe dream. And the culprit? None other than super-agent Scott Boras.

Scott Boras and Alex Bregman are why Kazuma Okamoto was never truly on the table for the Red Sox

Bregman remains Boston’s top target this offseason, so any flirtation with Okamoto wasn’t about pressuring him—it was doomed from the start.

Here’s the obvious truth: Okamoto and Bregman are both repped by Boras. As talented as the NPB standout is, he’s MLB-untested and wasn’t commanding the massive payday Bregman expects.

Boras plays the long game, prioritizing a lucrative, multi-year megadeal for Bregman over Okamoto’s modest four-year, $60 million pact with Toronto. He also knows the Red Sox are desperate to bring back their 2025 standout.

No way Boras lets Boston use Okamoto as bargaining chip against Bregman. Try it, and he’d dangle Bregman straight to the Jays as payback. The Sox might have eyed the six-time NPB All-Star seriously, but he was always Plan B at best.

Case in point: Right after Okamoto signed, reports surfaced of the Red Sox dropping an aggressive offer on Bregman. That’s no accident. Boston’s been quiet in free agency all winter, but with Boras holding the cards, they finally revved up.

One bid doesn’t seal the deal—Boras loves drawing these out. But it’s a step forward from the standoff. Okamoto? He just kickstarted the talks. End of story.