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Former Cubs executive is set up to play spoiler in the Alex Bregman sweepstakes

A hush has largely settled over the sport in recent days, but that won't last long, especially with multiple signing deadlines looming, the biggest being Japanese right-hander Tatsuya Imai, who has until Jan. 2 to sign with an MLB team. The Chicago Cubs are among a handful of teams that have been connected to him of late.

Once Imai comes off the board, the rest of the starting pitching market will likely start to move - and the Cubs figure to be active there, one way or another. But the most persistent rumors of the winter continue to connect Chicago to Alex Bregman, who opted out of his deal with the Boston Red Sox at the end of the 2025 season in pursuit of big money.