Cubs Eyeing Free Agent Starter With 'Big Upside'

In a November 13 article from The Athletic, Chicago Cubs general manager Carter Hawkins was quoted as saying, “If you look at our current lineup, our current depth chart, where are we most likely to be able to improve? It’s going to be on the pitching side. That’s where the most opportunity is.

"It’s not that we wouldn’t acquire an awesome position player or be active on the position-player market in different ways. But it’s just most likely that it’s going to be in the pitching space where we find things that make us better for the cost that we’re looking to be paying at that time," Hawkins continued.

This sentiment doesn't come as a surprise, as a look at Chicago's roster shows that they're in a solid spot when it comes to their position players, but could use added depth and firepower in both their starting rotation and bullpen. Luckily for them, there are a plethora of appealing options to pursue in free agency or via trade.

New Chicago Cubs general manager Carter Hawkins speaks after being introduced Monday, Oct. 18, 2021. | IMAGO / ZUMA Press Wire

One pitcher the Cubs have a reported interest in is former San Diego Padres pitcher Dylan Cease. However, Cease isn't the only pitcher on the Padres' 2025 roster that Hawkins, president of baseball operations, Jed Hoyer, and the rest of the Cubs' brass are watching right now.

Cubs Having Interest in Michael King

According to a November 14 article from MLB insider Sahadev Sharma and Patrick Mooney of The Athletic, Chicago's front office has former Padres pitcher Michael King on their free agency radar, as they believe he has "big upside when healthy".

King would make a lot of sense for the Cubs. While he missed about half of the 2025 regular season with a shoulder and then a knee injury, he produced a solid 3.44 ERA and 76 strikeouts in 73.1 innings pitched when he was able to take the mound.

The 30-year-old did stay healthy for San Diego in 2024, amassing a stellar 2.95 ERA and 201 strikeouts in 173.2 innings pitched, which is a large reason why he's one of the more sought-after arms available this winter, despite missing time in 2025.

1: Michael King, SP
Projected Contract - 4 years, $88M

There are reports that the Cubs are pursuing top free agent starters, but I still have trouble believing they will spend big.

Michael King will likely be a cheaper option, but is someone who can still be a big contributor. pic.twitter.com/qI65dj1VM9
— The Wrigley Wire (@TheWrigleyWire) November 14, 2025

Spotrac projects that King will sign a six-year, $141 million contract this offseason. While that would make for the second-most money Chicago has ever given a pitcher (only short of the $155 million that Jon Lester signed for in 2015), there's a chance this contract could look like a steal by the time it's over if King can keep healthy and perform to his potential.

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