Tarik Skubal to the Cubs has always sounded like the kind of idea that lives more in wishful thinking than reality. Chicago has been linked to him before, including at the recent MLB trade deadline, but the left-hander ended up with the Los Angeles Dodgers. And for all the obvious reasons the Cubs need pitching, the price tag has always looked like the bigger obstacle than the fit.
That’s why Jeff Passan’s latest report from ESPN stands out. He wrote that the Cubs “badly want Skubal,” even while noting they may be skeptical about going to the kind of money it would take to land him.
Passan added that Skubal could command “well in excess of $300 million, potentially in the $400 million-plus range.” He also identified the Dodgers and New York Mets as the most obvious suitors, while pointing to the San Diego Padres as another team that needs a rotation anchor with Michael King and Nick Pivetta set to hit free agency.
For Chicago, this is where the conversation gets interesting. Wanting Skubal is one thing.
Actually paying for him is another. That’s been the Cubs’ reputation for a long time, and it’s still part of the backdrop here.
But the last year-plus has shown a different edge from the front office, starting with the five-year, $175 million signing of Alex Bregman.
The Cubs also aren’t operating like a team that’s content to wait around. They’re in a win-now window, they believe they can chase a World Series, and their trade deadline made that clear when they added multiple high-profile players for a postseason push that ultimately fell short. They’ll enter this offseason with plenty of money to spend and a glaring need at the top of the rotation.
That’s why Skubal keeps hanging over this discussion. Even if Chicago is more likely to land an arm a tier below, like Michael King, the possibility of going all the way is still there. The smoke around the Cubs and Skubal has lasted long enough that it’s fair to wonder whether there’s real heat behind it.
If the Cubs can patch the rotation, they’ll look like a true World Series threat. They already had one of the better two-way teams in baseball, and Pete Crow-Armstrong gives them a real superstar to build around. Add the best pitcher in baseball, and the whole picture changes fast.
Still, there’s a reason the Cubs aren’t viewed as the favorite. That hasn’t changed. But Jed Hoyer has shown a willingness to alter his team-building approach over the past year, and the boldest move left on the board would be the biggest one of all.
In Other News...
Alex Bregman Just Gave Cubs Fans Real Reason To Believe
After missing out on him in free agency the year before, the Cubs finally landed Alex Bregman on a five-year deal and got the kind of middle-of-the-order presence they had been chasing. The start was quieter than anyone in Chicago probably wanted, but Bregman settled in and finished with a .265/.355/.464 line, 28 home runs and a 128 wRC+, production that put him among the better third basemen in the league and earned him a finalist spot for the National League Silver Slugger Award.
What matters most for the Cubs is how he closed the season, because the late surge did more than clean up the numbers. It gave the lineup a more reliable tone heading into 2027 and offered a reminder that the signing was about more than name value, with Bregman looking like a player who can anchor the offense when it matters most. [Read more 🡒]
Cubs Suddenly Have More Pressure To Chase This Pitching Target
Kaima Taira is suddenly on the board, and that matters for a Cubs team still looking for more certainty in the rotation. ESPNs projection of a five-year, $72.5 million deal gives a sense of the market for the Japanese left-hander, who was cleared to negotiate with MLB clubs after leading NPB in ERA and ERA+ last season. For a Chicago team with both a need for starting pitching and the financial room to make a real bid, the fit is obvious.
The timing adds another layer of pressure. Because the NPB and MLB agreed to a modified posting window this offseason due to a pending lockout, teams have only 30 days to get a deal done, which compresses the process and rewards clubs ready to move quickly. The Cubs are viewed as a potential suitor, and if they want to stay in the conversation, they may need to act before the market tightens and the competition gets even more serious. [Read more 🡒]
Cubs May Finally Have A Real Shot At Freddy Peralta
Freddy Peraltas market is already drawing attention as the right-hander heads toward free agency, and the Cubs make a lot of sense as a team to watch. Chicago has been looking for more dependable starting pitching, and Peralta fits the kind of arm that can change the shape of a rotation if the price and term line up.
What makes him especially intriguing is the way his game has evolved, with his recent success giving clubs reason to believe there is still another level to tap into. The fit is obvious enough that speculation has already started to build around where he could land, but the real question for the Cubs is whether they are willing to move quickly enough to turn interest into a serious pursuit. [Read more 🡒]