In hindsight, Game 163 of the 2018 season served as something of an inflection point in the NL Central. The Chicago Cubs' brief but powerful reign was over, and in their place came the upstart Milwaukee Brewers, who have simply refused to let their hand off the wheel ever since.
Including that 2018 division title, the Brewers have won six of the past nine NL Central crowns. The Cubs, meanwhile, have won just once, in the pandemic-shortened 2020 season. And whereas the North Siders haven't made it past the NLDS in that time, the Crew have three NLCS appearances to their name, including the most recent one in 2026 that gave way to their first-ever World Series trophy.
Considering the payroll disparity between the two franchises -- not to mention Craig Counsell defecting from Milwaukee to Chicago mid-way through this recent run of dominance -- all of that isn't really a glowing review of the Cubs. Thus, it appears they're ready to leave no stone unturned in their efforts to wrestle control of the NL Central back from the Brewers, including the nuclear option: signing Tarik Skubal.
Cubs may want Tarik Skubal, but he won't bridge the gap between them and the Brewers
According to ESPN's Jeff Passan, the Cubs "badly want" Skubal. The MLB insider cautions that they're unsure if they can compete with the Dodgers and Mets in terms of dollars, but their interest is absolute.
While we could wax poetic about how the lone big-market team in the division cosplaying as a small-market one is ridiculous, it's telling that the Cubs are gearing up for a run at the best pitcher in the world during this truncated offseason. Their pitching staff (particularly the rotation) needs a head-to-toe makeover; as great as Skubal is, he's just one man. He can change the complexion of a starting five, but he can't literally account for every spot.
The money part of the conversation is a real concern, since the Cubs don't like giving pitchers long-term contracts (and that's in normal conditions when a lockout isn't on the horizon). But it's probably more of that quantity vs. quality conversation that will really hold them back. Spending $40-50 million on one starter doesn't leave a lot of room for them to address other weaknesses, which include the rest of the rotation, their high-leverage relief corps, and the corners of the outfield.
It's also a remote possibility that the Cubs saw what the Brewers did to the Dodgers in the NLCS and are wrestling with a blatant truth: They're not one starter away from climbing back to the top of the division. Skubal got just one chance to beat the Crew in the playoffs and failed. Even if they sign him, the Cubs will still be looking up at the reigning champions.
