Cubs’ biggest obstacle to a Kyle Tucker extension has nothing to do with Tom Ricketts

The Chicago Cubs walked off the Los Angeles Dodgers on Tuesday night in what was easily the best game of the 2025 MLB season so far. Chicago's bullpen appeared to have cost the team again, as L.A. put up a five-spot in the top of the seventh to turn a 7-5 deficit into a commanding 10-7 lead. But as they've done all year, the Cubs offense rallied: Catcher Miguel Amaya launched a game-tying solo homer in the ninth, and Ian Happ walked it off with an RBI single in the 10th.

And at the heart of things, once again, was outfielder Kyle Tucker. Chicago's prize offseason acquisition continued his torrid start to the year, reaching base four times — including a big two-run homer in the eighth that set up Amaya's heroics an inning later.

Oh, did we mention he also stole two bases for good measure? His latest effort his Tucker's OPS all the way up to an eye-watering 1.070; his 25 RBI and 65 total bases lead the Majors, and he's been the best hitter on a Cubs offense that has propelled the team to the top of the NL Central so far.

That seems like the sort of player any team would like to have around for the long haul. But unfortunately for Chicago, every big Tucker moment will be undercut by his looming free agency — and while Cubs fans are right to celebrate a huge win over an NL rival, it's hard to ignore the elephant in the room.

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Time isn't on Cubs' side when it comes to Kyle Tucker extension

Hours before first pitch on Tuesday, MLB Network insider Jon Heyman offered an update on where things stand in extension talks between Tucker and the Cubs. Or, rather, he offered a non-update, because the two sides haven't even started speaking yet.

This jives with everything we've heard so far: While president Jed Hoyer and owner Tom Ricketts have sworn up and down ever since they acquired Tucker that they intended on keeping him around beyond 2025, we've yet to see actions to back up those words. And while there is technically still time to change that, history isn't on the team's side here.

The biggest reason to be skeptical of Chicago's ability to sign Tucker long-term is Ricketts himself: He's stubbornly refused to flex the financial muscle you might expect from one of the richest teams in one of the biggest markets in baseball, and Tucker will expect a deal that figures to be at least twice as large as the richest in franchise history (eight-year, $184 million contract Chicago handed to Jason Heyward before the 2016 season).

But beyond that, it's also worth noting just how historically unprecedented a deal at this stage would truly be. While Cubs fans can point to Vladimir Guerrero Jr. signing a $500 million extension with the Toronto Blue Jays after Opening Day, that's the exception that proves the rule: Star players rarely sign deals with just a year to go before free agency, and doing so after their walk year actually begins is even rarer.

There have been players who opted to forgo hitting the market: Mookie Betts' $365 million deal with the Dodgers came months before he was set to hit free agency, for example. But Betts signed that deal on July 22, with the future of the sport still very much in flux amid the COVID-19 pandemic. Francisco Lindor signed a megadeal after being traded to the New York Mets, but that came just prior to Opening Day. There simply aren't many examples of this sort of contract getting done at this point.

Maybe Chicago will prove the exception to that rule. Maybe Tucker will fall in love with Wrigley as he helps slug the Cubs into contention this summer. But there are plenty of factors working against Ricketts and Co. here, namely the fact that every day brings Tucker one day closer to opening up the bidding to all 30 teams. That will likely force Chicago to do something it has been loath to do: Blow the market out of the water.