Cubs Have Reportedly Had ‘Casual Discussions’ About Alex Bregman on Short-Term Deal

The Cubs have one of the best farm systems in baseball, with seven prospects in MLB Pipeline’s top 100 list. The best of those is Matt Shaw, who is on pace to debut with the team in 2025. While it isn’t set in stone, odds are he’ll be in Japan on Opening Day. If he ends up winning the Rookie of the Year award and he’s up all season, the Cubs will get an extra draft pick in return. Therefore, I don’t see a reason to keep him down and start someone like Gage Workman at third base instead.

After a recent report from Bruce Levine of 670 the Score, however, it’s fair to say that Shaw may not be the third baseman at all. Levine said the Cubs have had “casual conversations” with Scott Boras about Alex Bregman, one of his stable of high-profile clients. It would have to be a short-term deal, something like three years with opt-outs after each of the first three seasons, which is only a possibility if Bregman can’t land something bigger.

While I have my doubts, this isn’t the first time Bregman has been mentioned as a possibility for the Cubs. Earlier this month, Jon Heyman said the Cubs had an “outside chance” of signing the former World Series champion. Boras is notorious for making sure his clients get as much money as possible, but he seemingly messed up last winter and let several of his big clients stay in free agency until February, which led to them all getting short-term deals with low values. Perhaps you’re familiar with Cody Bellinger.

Boras doesn’t seem to be dragging his feet as much this offseason, but Bregman still needs a home as his asking price remains high. Multiple teams have interest, it’s just that no one wants to pay what Boras and Bregman are asking for.

It’s been made clear that Jed Hoyer doesn’t like to do long-term deals, as there is much more risk involved. While it wasn’t perfect, Bellinger’s three-year deal was right up the Cubs’ alley. With opt-outs after each of the first two years, there wasn’t much risk for either side. Whether it’s just anecdotal or sourced info, that’s the same thing Levine is saying about Bregman. I’m sure Hoyer dreams of getting star players on short-term, high average annual value deals every winter, which is why I wouldn’t be shocked to see them pounce on this before another team comes to their senses.

Hoyer and the front office know they have plenty of talent in their farm system, and Shaw is someone I’ve heard nothing but outstanding things about when talking to experts around the league. If Bregman does choose the North Side, Shaw would be without a regular spot for the immediate future. That could be for the best, as rushing him into the starting role at third base comes with a lot of risk and pressure. Since Shaw can play multiple positions, one option is making him a super-utility guy off the bench.

My favorite option if the Cubs were to sign Bregman, as much as it may hurt, is trading Nico Hoerner. Multiple teams have shown serious interest in Hoerner throughout winter, including the Mariners and Yankees. Moving Hoerner would allow Shaw play second base with Bregman at third. Almost every mock trade including Hoerner has been centered around the idea of the Cubs receiving pitching in return, and that’s exactly what I would do in this scenario.

Whether it’s the Mariners, Yankees, or someone else, pitching needs to be the focus. This current Cubs roster still needs a starting pitcher and late-inning reliever. If there’s a team willing to send one, or even both, of those pieces back to Chicago, I’d expect a deal could easily come to fruition.

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