MLB’s top brass are meeting in Orlando this week and that generally sets the stage for getting at least a few deals done. This year’s Winter Meetings have not disappointed, with closer Edwin Díaz switching
teams and coasts as he signed a three-year deal with the Dodgers and slugger Kyle Schwarber resigning an even larger contract that likely has the left-hander setup to end his career in Philadelphia. The Cubs haven’t pulled the trigger on any big deals this week, but we did get this tidbit from a Foul Territory interview with The Athletic’s Sahadev Sharma:
Let’s get the obvious out of the way: it is objectively good news that the Chicago Cubs, one of baseball’s true juggernauts of a brand has decided to engage with the top of the free agent market again. I mean that sincerely. And also, the real question is why has one of baseball’s crown jewel franchises been complacent to sit that out for years now? More from PJ Mooney and Sharma:
The Chicago Cubs are targeting a higher level of the free-agent market and signaling an openness to spending for certain players, according to team and league sources briefed on the club’s deliberations.
Reading that sentence, Cubs fans may understandably roll their eyes.
After all, this is a multibillion-dollar franchise with generations of loyal customers, a valuable multimedia portfolio and an iconic ballpark that anchors the surrounding real-estate empire. A big-market team that wins 92 games and a playoff round is supposed to keep going for the World Series.
This article goes on to tout their pursuit of Dylan Cease, Alex Bregman and Michael King.
I’ll spot the authors that Cease and Bregman represent the top of the free agent market. I’m not entirely sure why the Cubs are interested in Bregman given his pull tendencies and hit spray charts that are unlikely to have the same impact in Wrigley Field’s deep left field that they’ve had on the Crawford Boxes and Green Monster, but that’s a Short Porch for another day.
Michael King, though? One of these players is not like the others.
According to MLB Trade Rumors, Michael King is the 14th ranked free agent in this year’s class. He’s ranked right after closer Díaz and right before another starter who’s been connected to the Cubs, Zac Gallen. To be clear, I like King a lot and think he’d be a good signing for the Cubs, but the thing that differentiates him from the top 10 is right in Mooney & Sharma’s own analysis:
King’s upside turned him into a key piece of New York’s blockbuster Juan Soto trade. In his first season with the San Diego Padres — and only full year in a major-league rotation — King finished seventh in the 2024 National League Cy Young Award voting.
That momentum slowed down due to various injuries (right shoulder inflammation, left knee inflammation) that limited King to 15 starts this year. During their playoff series at Wrigley Field, the Padres used him out of the bullpen for one inning in the elimination game they lost.
Heading into his age-31 season — and coming off an injury-plagued year — it’s unlikely King will get an extremely long deal or an exorbitant guarantee. That’s also part of what makes him so appealing.
Guy with lots of upside? Check. Injury concerns making it likely they’ll accept a short-term, high AAV deal? Check. Taking on injury risk rather than salary risk? Check.
This isn’t turning over a new leaf being “in on” the top of the market. It’s Hoyering 101: while everyone else runs the prices up on the elite, proven talent getting long-term deals that exceed the Cubs largest contracts of all time*, see if you can find a reliable used Prius that’s still got some good miles on it.
*Still Jason Heyward’s not exorbitant at all eight year, $184 million deal from 2015.
