Chicago Cubs Should Keep Tabs on Two Remaining Star Free Agents

The Chicago Cubs have had a great offseason but could take it to another level if they were able to sign either of these remaining free agents.

Oct 25, 2024; Los Angeles, California, USA; Los Angeles Dodgers pitcher Jack Flaherty (0) pitches in the fifth inning against the New York Yankees during game one of the 2024 MLB World Series at Dodger Stadium. | Kiyoshi Mio-Imagn Images

This offseason has been a successful one for the Chicago Cubs, who saw an opportunity to potentially seize control of the National League Central and took it.

With the Milwaukee Brewers and St. Louis Cardinals both taking a step back and the Pittsburgh Pirates still refusing to spend money, the top spot in the division was up for grabs between them and the Cincinnati Reds.

The Reds made a few moves to upgrade their roster, but they didn’t come close to making the kind of upgrades that the Cubs have made.

Chicago completed arguably the most shocking trade of the winter, acquiring star right fielder Kyle Tucker from the Houston Astros.

It was not cheap, considering that he is a free agent after the 2025 campaign, as they sent third baseman Isaac Parades, pitcher Hayden Wesneski and star prospect Cam Smith to the Astros.

Tucker is certainly talented enough to take a one-year gamble on as a rental, but that could hurt in the long run if he doesn’t sign a long-term deal with the team. Smith is already one of the best prospects in the sport after being selected in the first round of the 2024 MLB June Amateur Draft out of Florida State.

Another reason the Cubs were comfortable making that deal is that it clears the runway for top prospect Matt Shaw to take over as the everyday third baseman.

Overall, this has been a solid offseason in Chicago, as they added depth to other spots on the roster.

Matthew Boyd was signed to round out the starting rotation after Kyle Hendricks departed earlier in the offseason. Eli Morgan was acquired for bullpen depth and catcher Carson Kelly was signed to complement Miguel Amaya behind the plate.

If the Cubs didn’t make another move all offseason, no one would bat an eye.

But, MLB expert David Schoenfield of ESPN believes the one thing they should be doing the remainder of the winter is keeping an eye on the markets of third baseman Alex Bregman and starting pitcher Jack Flaherty.

Both Scott Boras clients haven’t found the kind of long-term offer they were hoping to when free agency began. That presents an opportunity for Chicago to swoop in and snag impactful players for what could be a team-friendly deal.

There have been reports that Bregman is not interested in a short-term deal, but the sides have had some casual conversations. Flaherty reportedly would be interested in a short-term deal with opt-outs that would enable him to hit the open market again after the 2025 season.

A starting pitcher isn’t their most pressing need, but if the opportunity to land a player of Flaherty’s caliber presents itself, they should strongly consider it. Teams can never have too much starting pitching for a marathon MLB year.