Cubs insider details strategic cost of Alex Bregman's potential arrival

Red Sox third baseman Alex Bregman is at a career crossroads this offseason. After establishing himself as one of the pillars of the Astros' late 2010s' dynasty, he signed a three-year, $120 million contract with Boston ahead of the 2025 campaign. However, he was immediately put into an iffy situation as he had to dislodge club star Rafael Devers on the hot corner. Devers was then traded to the Giants in a move that made Bregman the undisputed star in third base.

However, injuries that spread throughout the clubhouse saw the Red Sox getting trounced early in the postseason. This led Bregman to opt-out after just the first year of his deal and become a free agent with rumblings stating that the Cubs could be a potential destination for the third baseman. On the most recent episode of the North Side Territory podcast, insider Shadev Sharma sounded off on how the Cubs could potentially land the hot corner star this offseason.

"If they're adding someone like Alex Bregman, it feels like they have to make a trade," said Sharma. "I'm not saying it has to be an infielder, I'm just saying there's not enough. Whether it's [Moises] Ballesteros, [Owen] Caissie, [or] Kevin Alcantara, these guys have to play. You can't just have them stay in Triple-A for the rest of their careers," he added. (4:28-4:50)

In 2025, the three-time All-Star third baseman posted a .273/.360/.462 slash line with an OPS of .821 with 18 home runs and 62 runs batted in. Sharma further discussed how much talent the Cubs have in their minor league system when it comes to position players.

Analyst reveals possible names that can be involved in Alex Bregman deal

Continuing on the same episode of the podcast, MLB analyst Shadev Sharma that outfield prospects Owen Caissie, Kevin Alcantara, along with back stop Moises Ballesteros, could possibly be dealt if the Cubs want to land Alex Bregman.

"Eventually, their value plummets if they're not played or moved. The Cubs have to make some decisions." (4:51-5:10)

Out of all the names that was mentioned by Sharma, Ballesteros has the most MLB experience under his belt after 20 appearances for the Cubs in the 2025 season. In terms of MLB Pipeline rankings, however, Caissie is regarded as the highest ranked amongst team prospects and is currently 47th across the majors.

With that being said it would be interesting to see how the club navigates the free agency market given that they're short on skilled infielders, especially on third base heading into 2026.

Edited by Daniel Santiago