Cubs poised to screw up rumored Tarik Skubal pursuit before it even begins

The offseason is upon us and the Chicago Cubs are wasting no time playing a tired song.

ESPN's Jeff Passan breaks down an array of MLB rumors, but specifically digs in on Tarik Skubal, the undisputed #1 free agent in this winter's class. As he points out, the left-hander and two-time Cy Young Award winner is expected to sign before owners lock out the players on Dec. 2, so the coming weeks could be very exciting.

The good news? The Cubs got a direct call-out in the rumor. The bad? It came attached with an exhausting schtick that's become all too familiar to the fanbase over the last decade.

"The Chicago Cubs badly want Skubal. They also are skeptical that they will be willing to compete at the sort of dollars Skubal is expected to get -- well in excess of $300 million, potentially in the $400 million-plus range."

Well, no duh. There's not a team in baseball that wouldn't like to add Skubal to its rotation in the years to come. It's going to come down to price, especially when you're talking about a record-setting number. Forget a $300 million deal - the Cubs have never even doled out a $200 million deal, with the high-water mark coming in Jason Heyward's contentious eight-year, $184 million contract more than a decade ago.

If the last two Octobers haven't taught Jed Hoyer and the Cubs the importance of having a true ace, then they'll never learn the lesson. In 2025, Chicago went with a bullpen game in a winner-take-all Game 5 of the NLDS against the Brewers and this year looked totally overmatched in the two-game sweep at the hands of the Padres.

Cubs signing Tarik Skubal in free agency would shock the baseball world

Nobody expects the Cubs to be the team that comes away with Skubal in the next month. It's not that they couldn't or lack the resources to do so - it's just that there's no track record of swimming in the deep end of the pool, let alone taking a swim in the ocean (and, let's be clear, that's what a Skubal signing would be).

Hoyer has always gravitated toward lower-ceiling, higher-floor pieces and B-list names, seemingly taking themselves out of the running whenever price tags get even a little uncomfortable. But you know, what. Prove me wrong, Jed. I'll happily eat crow and admit I was wrong.

This is a Cubs team that doesn't just need to replenish its pitching staff in terms of depth. They need an ace and there's one who's head and shoulders above the rest and they need to step up and rewrite the narrative in their pursuit of him this month.

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