The Chicago Cubs are known to be interested in third baseman Alex Bregman. This is now the second straight offseason that the Cubs have pursued the three-time All-Star.

Last offseason, the Cubs offered Bregman a four-year, $115 million deal. That multi-year deal wasn’t enough, as he signed a three-year, $120 million contract with the Boston Red Sox. Since the veteran has opted out of that deal, he will be a free agent yet again.

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After missing out on him last offseason, the Cubs could land the 31-year-old in free agency this winter. The front office has already met with him via Zoom, and the interest feels real from both sides.

Some insiders also predict Bregman to land in the Windy City. Gabe Lacques of USA Today recently labeled the Cubs as the perfect landing spot for the veteran third baseman.

“Even as Matt Shaw showed some viability in his rookie season, there’s still plenty of room for Bregman, whose 128 adjusted OPS would be a massive upgrade over Shaw’s 98,” Lacques wrote. “Hoerner’s potential departure would allow room for both on the dirt in 2027.”

There is a real world where the Cubs do land Bregman this offseason. The team appears to be in the market for a potential power bat, and the former Red Sox infielder would be the perfect replacement for Kyle Tucker.

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However, it’s hard to imagine the Cubs meeting Bregman’s contract demands this offseason.

In a recent article on ESPN, Jeff Passan highlighted that Bregman is seeking a six-year deal in free agency. That puts his potential contract in the price range of $160+ million over those six years.

Kiley McDaniel of ESPN also recently updated Bregman’s projected deal this winter. He believes the All-Star third baseman will now sign a five-year, $170 million deal or agree to a six-year contract with a lower average annual value (AAV).

Therefore, Bregman’s asking price might draw him away from the Cubs. Committing six years to a soon-to-be 32-year-old is probably not something the front office wants to do, and it’s highly unlikely Chicago will outbid other teams for the veteran.

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That makes it difficult to see Bregman landing with the Cubs.

The only way the North Siders could land him is if he opts to sign a shorter-term deal. But after signing a shorter deal last offseason and then opting out of that contract, the two-time World Series champion likely won’t settle for that.

So, if Bregman is set on receiving a six-year deal this offseason, the Cubs might not land him after all.