Top MLB Insider Shreds Team After Red Sox Sign Alex Bregman

The Red Sox reportedly were “most worried” about the Cubs in the Alex Bregman sweepstakes, but they apparently should not have been.

After Craig Breslow and company convinced Bregman to come to Boston, reports about the other offers fielded by the star infielder started to come out. Arguably the most surprising of the group was the reported offer out of Chicago, where the Cubs reportedly weren’t the highest bidder in any of the three main contract facets: years, annual value and total value.

That didn’t sit well with Ken Rosenthal, who recalled Theo Epstein asking, ‘If not now, when?’ after Chicago made a blockbuster trade for Aroldis Chapman en route to the 2016 World Series title. The Cubs aren’t in the same scenario as they were in that championship-winning season, but The Athletic insider still thought Chicago missed an ideal time to strike.

“Alex Bregman, for them, presented an opportunity,” Rosenthal said on “Fair Territory.” “A pretty rare opportunity at a moment in time when they should have been ready to strike. Why was Bregman such a rare opportunity? This is perhaps the only year the Cubs will have Kyle Tucker. So, you’ve got one year of Kyle Tucker. You’ve had years in which you were financially disciplined, cutting the payroll, trying to put yourself in a position where when an opportunity like Bregman arose, you’d be ready to go.

“Well, what do the Cubs do? They made the fourth-highest offer behind the Tigers, behind the Astros, behind the Red Sox. I’m talking about total guaranteed money. Obviously, they didn’t get the player. So, I was critical of them. If not now, when? That’s the question Theo asked and Tom Ricketts — his answer lately seems to be ‘never.’ When you’re charging among the highest ticket prices in the game, that’s a problem.”

The Cubs’ follow-up move after losing Bregman almost made the situation in Chicago even worse. Justin Turner is a tremendous leader who can provide a decent amount to a club, but the 40-year-old won’t turn Chicago into a legitimate playoff contender like Bregman would have.

Thus, Rosenthal’s roast wasn’t reckless, and Cubs fans now will have to remain patient as the organization slowly rebuilds.