Copyright Newsweek

The Boston Red Sox went all in for free agent superstar Alex Bregman last offseason. They landed him on a massive deal, but he opted out of his contract after one year in Boston. With Bregman sitting in free agency, the Red Sox are going to need to win the sweepstakes all over again. He was a crucial piece of their team this season, so re-signing him likely sits at the top of their list of priorities this winter. NBC Sports' Matthew Pouliot recently projected Bregman would sign a massive five-year deal worth $160 million in free agency this winter. "Bregman didn’t get the long-term deal he wanted last winter, settling for a three-year, $120 million pact with Boston that gave him the right to opt out," Pouliot wrote. "Now he’ll give it another try after a season in which he was fantastic for two months before missing 43 games with a quad injury. "He continued to produce initially after returning, but he hit just .180/.273/.262 in his final 31 games, dropping his OPS from .933 to .821. Bregman remains a strong defender, and he’s showed an impressively steady bat since his steep decline from his near-MVP campaigns in 2018 and ’19. Still, it’d be dangerous to give him the kind of rest-of-career contract he obviously desires." The Red Sox jumped through hoops to land Bregman last offseason, but it seems like they're going to need to do the same thing to sign him again. A five-year deal like this would certainly give Bregman more financial security. He would be locked in for five years rather than two. The average annual value of his deal would be slightly lower, but it gives the star some longer-term financial security.