The length of David Stearns’ last contract extension with the Brewers wasn’t made public when the deal was announced in January 2019, though according to ESPN.com’s Buster Olney, Stearns’ pact will be up at the end of the 2022 season.  Details of Stearns’ first contract with the team also weren’t known, though given the reported terms of the extension, it would hint that Stearns initially signed a four-year deal covering the 2016-19 seasons, thus making his extension a three-year pact.

After first being hired as general manager, Stearns received a promotion to president of baseball operations in his last deal.  Regardless of the title, Stearns’ stewardship of the Milwaukee front office has led to plenty of success.  The Brew Crew have reached the postseason in each of the last three years, and that streak will almost certainly stretch to a fourth year considering the club’s healthy lead in the NL Central.  Milwaukee’s .607 (82-53) win percentage is the fourth-highest of any team in baseball, and the Brewers look like a strong contender to reach the World Series for the second time in franchise history.

Amidst this track record, it is still rather remarkable that Stearns doesn’t even turn 37 years old until February.  If he did enter the open market, it is easy to imagine any number of teams pouncing at the opportunity to hire Stearns to take over their baseball ops department.  Within the last three years, the Giants and Mets each reached out to the Brewers to ask if Stearns could be interviewed for their own front office vacancies, only for Brewers owner Mark Attanasio to deny both requests.

The Mets’ request came just last winter, and they loom as an obvious suitor given the ongoing upheaval in their baseball operations department.  Olney observes that hiring Stearns would be a natural way for Mets owner Steve Cohen to clean house after the tumultuous season, especially given Stearns’ ties to the organization — Stearns is from New York, grew up a Mets fan, and worked as a baseball operations intern for the team in 2008.

What isn’t known, of course, is whether Stearns has any interest in leaving the Brewers.  The two sides still have more than a year to negotiate another extension.  In fact, given the lack of public knowledge about Stearns’ other contracts, it isn’t out of the question that he might already have another extension worked out, and the new deal simply hasn’t yet been announced.

Moving to New York or another larger-market team would offer more payroll flexibility but also much more pressure and media scrutiny.  Stearns would also be taking on the x-factor of working with a new owner like Cohen, as opposed to his familiar relationship with Attanasio.  It is also worth mentioning that while the Brewers have had modest payrolls overall, it isn’t as if Attanasio hasn’t been willing to spend big in certain situations (such as Christian Yelich’s nine-year/$215MM extension, or Lorenzo Cain’s five-year/$80MM free agent deal).  Going forward, the Brew Crew will face some interesting decisions this winter thanks to a pricey arbitration class, yet their proverbial window of contention certainly looks to remain open for the next few seasons.

Should the Brewers win it all this October, however, it is possible that Stearns might view his Milwaukee tenure as a completed challenge, and he’ll then look at his next step.  With only a year left on his contract, Stearns has some leverage to possibly prevent Attanasio from blocking meetings with other teams, so Stearns could at least hear what some other suitors have to say.  As one rival executive suggested to Olney, the Brewers could potentially even work out a trade to receive compensation from another team that wants to hire Stearns before his contract is up, similar to how the Cubs worked out a deal with the Red Sox when Theo Epstein was hired away with a year remaining on his Boston deal.