Alex Bregman free agency: Why Matt Chapman's contract extension could mean a bigger payday for Astros star

The first major deal of the offseason was struck weeks before the postseason. Late Wednesday night, the San Francisco Giants locked up third baseman Matt Chapman to a six-year, $151 million contract extension. Chapman was expected to decline his $17 million player option after this season to re-enter free agency. Instead, he has a long-term deal in place.

This past offseason, Chapman was one of the "Boras Four" along with Cody Bellinger, Jordan Montgomery, and Blake Snell. All four settled last in the winter (or even the spring) for one-year contracts with player options rather than big money long-term deals. All told, Chapman is tied to the Giants for seven years at $169 million from 2024-30, just shy of Kris Bryant's contract with the Colorado Rockies (seven years, $182 million).

Chapman's extension would seem to be good news for another free agent-to-be third baseman: Alex Bregman. Our R.J. Anderson ranked the longtime Houston Astros star as the No. 3 free agent for the coming offseason, three spots ahead of Chapman. Here's the write-up:

It'll be interesting to see how teams value Bregman. He's far enough removed from his best slugging years that we assume they'll value him for what he is: a skilled contact and on-base merchant with a good glove and the ability to hit around 20 home runs (we don't think he'll find a ballpark fit as beneficial as Houston's, meaning the 25-plus homer threshold might end up being beyond his reach). Adding to the intrigue is the fact that he's had an odd season, hitting the ball hard more frequently than normal while also walking far less often and having to fight uphill after a poor start.

Bregman, 30, is in the final season of the five-year, $100 million extension he signed in March 2019. That contact bought out his three arbitration years plus two free-agent years. That means he will become a free agent for the first time this winter. Like Chapman, Bregman is a Scott Boras client. In spring training, he gave a stock answer when asked about a possible extension with Houston.

"I'll just be focused on playing ball and letting (Boras) take care of that with them. We're listening," Bregman told The Athletic in March. "I'm just ready to play. I'm enjoying being around all these guys and playing and competing and getting ready for the start of the season. I'm not really treating it like (a contract year). I'm treating it like another season, trying to have a good year."

What does Chapman's extension mean for Bregman? How does it affect his market? Let's dive into Bregman's free agency. 

Bregman compares favorably to Chapman

Bregman is almost exactly one year younger than Chapman, meaning he will enter free agency this winter the same age Chapman was last offseason. Bregman's performance in the three years leading up to free agency is better than what Chapman put together during the same period of his career. Here's the comparison:

Chapman is an excellent defender. Not as dynamic as he was at his peak, but still excellent. Bregman is no slouch at the hot corner himself though. If there is such a thing as a "clutch" defender, it's Bregman. He has a knack for making standout defensive plays in important situations. Bregman also offers a much lower strikeout rate than Chapman and better on-base chops.

Also, Bregman is a proven postseason performer. Chapman has only played in six playoff games in his career. That's not his fault -- blame the teams he was on -- but Bregman has played in 97 postseason games with Houston and has played well in those 97 games. Fair or not, there is more certainly about Bregman performing in a demanding market and in October.

One more thing to keep in mind: Chapman had a very poor finish to 2023. He hit .384/.465/.687 in April and .205/.298/.361 the rest of the season. There were some questions about his bat entering free agency. Bregman has done the opposite. He started this season slowly (.201/.270/.264 in his first 37 games) before really picking it up (.285/.336/.521 in 89 games since).

Bregman now compares favorably to Chapman entering free agency a year ago. He compares less favorably to this year's version of Chapman, the one who secured a six-year contract worth $151 million, though he is a year younger. You needn't try hard to see Boras marketing Bregman as a better player than Chapman, and thus deserving of a larger contract.

There's one fewer free-agent option at third base

Like everything else, supply and demand drives free agency, and teams that need help at third base now have one fewer free-agent option. This works both ways -- Bregman lost a suitor because the Giants no longer need a third baseman -- but Bregman is now the only high-end third baseman set to hit the open market. Teams interested in adding an impact player at that position have only one place to turn. There will be more demand (third base-needy teams) than supply (Bregman), which sets him and Boras up for a bidding war. Chapman's extension reset the market in a favorable way and now Bregman has less competition in free agency.

Which teams could be interested?

The Astros, for starters. Prospects Zach Dezenzo and Shay Whitcomb haven't impressed in limited big-league time this year, so unless Houston is willing to deal with a young player's growing pains, they don't have an in-house replacement for Bregman. And hey, maybe they are willing to go young. They let Carlos Correa leave and replaced him with Jeremy Peña, remember.

The two New York teams could have interest too. The Mets could let Pete Alonso walk, slide Mark Vientos to first base, and install Bregman at the hot corner. The Yankees could let Gleyber Torres leave, move Jazz Chisholm Jr. to second, and sign Bregman to play third. Farfetched? Eh, maybe, but I bet we hear the Mets and Yankees touch base with Bregman at some point this winter.

I'm not sure I'd bet on them opening their wallet, but the Seattle Mariners desperately need offense, and have a gaping hole at the hot corner. As an added bonus, they'd steal Bregman away from a division rival. The Toronto Blue Jays need to do something after their disappointing season. Maybe the up-and-coming Kansas City Royals are ready to spend in a big way?

You can never rule out the Mystery Team with Boras either. Who had the Arizona Diamondbacks signing Montgomery? Remember when the Mets wouldn't sign J.D. Martinez because they didn't want to block Vientos? You can even go back to Boras getting Eric Hosmer an eight-year deal from the San Diego Padres. You should never rule out the possibility of a surprise team with Boras.

Bregman is, at worst, a comparable player to Chapman, and he is about to enter free agency with a new data point to reference in contract talks, and with one fewer third base alternative available. Free agency doesn't always go according to plan (see: Chapman last year), but all signs point to a favorable market for Bregman as the offseason inches closer.