The Chicago Cubs suffered an earlier postseason exit than they were hoping for, falling to their hated rival Milwaukee Brewers in Game 5 of the NLDS in what was their first real playoff run in close to a decade.

Winning October games at Wrigley Field served as a reminder of the potential of what this team and city can look like at its peak, and now president of baseball operations Jed Hoyer is hungry for more as it tries to figure out how to improve for next season and make an even deeper run.

For large portions of this past season, it was the offense carrying the load as the bats put up some historic numbers over the first several months of the season. Though things would balance out, it’s no secret that this team’s weakness was pitching.

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There were some heroic performances from guys during the playoffs, especially after the loss of rookie sensation Cade Horton, but it simply became obvious that the depth just was not there, and Chicago really lacked a true ace all season long.

The Cubs are expected to add to the staff this winter via free agency, but it’s clear that what they need is an alpha dog at the top of the staff who can dominate his way through a full season. Though it may be hard to find someone like that on the open market, signs are pointing to one becoming available.

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Soon-to-be repeat American League Cy Young Award winner Tarik Skubal is facing a conundrum with his current team. With only one year left of team control before the big left-hander hits free agency for what will likely be a record-breaking contract for a pitcher, the Tigers appear unlikely to keep him beyond 2026.

Detroit has been trying for over a year to work out an extension, but Skubal — a Scott Boras client — appears bound to become a free agent and field some absolutely massive offers. This leaves the Tigers in a situation where they can either trade him now for a massive haul, or risk losing him for nothing after one more season.

Skubal being at least shopped around seems to be very likely this winter, and if that does happen, Chicago absolutely needs to be one of the teams involved.

Here are three reasons why it makes a whole lot of sense.

Cubs Have Ammunition to Go Land Skubal

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If the Tigers are going to trade Skubal, it’s going to be for a Godfather sized offer, and Chicago is one of the only teams in baseball with the combination of the prospect capital and big league talent to go get him.

Skubal would cost a ton, and a trade here would likely include parting with guys that fans may not be comfortable parting with. Someone like Cade Horton and another established big leaguer comes to mind, and Detroit would be well within reason asking for someone like Owen Caissie, Moises Ballesteros or Jaxon Wiggins as the centerpiece of a prospect return.

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All of this return for one season of Skubal is a tough sell — especially given the potential Cam Smith showed following a trade to the Houston Astros for one year of Kyle Tucker -— but that mindset undercuts the impact that Skubal would have.

Simply put, Skubal is the best pitcher on the planet and makes this team instantly potentially even a World Series favorite, and if the Cubs were serious, they would make a genuine offer to keep him beyond just 2026 as well.

Adding an ace to the top of the staff instantly takes a group with some potential (if they stay healthy) to arguably the best rotation in all of baseball. If Skubal really does end up on the trade block, Chicago and Hoyer should be one of the first calls the Tigers receive.

Cubs Need to Find Way to Catch Brewers

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After paying Craig Counsell a historic contract to come over from Milwaukee prior to the 2024 season, Chicago has finished behind them in the division twice and now lost a playoff series as well. The Brewers are not going anywhere either, and until further notice, the division is theirs to lose.

Perhaps they thought it was the Tucker trade, but the Cubs need to make a move to put themselves over the top, not just in the regular season, but in the playoffs as well. Chicago has not won the division in a full season since 2017, and Counsell was supposed to change that.

Hoyer must give him the tools to make that happen, though, and a trade for Skubal would be the biggest tool yet. If the Cubs are serious about taking back this division, they are going to need a legitimate ace, and Skubal would be that and more.

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