

The Chicago Cubs have been known to take risks on pitchers. That was surely the case last year, as the front office acquired pitchers like Brad Keller, Drew Pomeranz, and even Matthew Boyd.
Keller had a 4.34 ERA in his first six seasons, Pomeranz hadn’t pitched in the Major Leagues since 2021, and Boyd only made eight starts in 2024 following his recovery from Tommy John surgery. All three of those pitchers were risky pickups by the Cubs.
Sometimes acquiring those high-risk pitchers turns into high rewards. Keller had his best season as a professional by finishing with a 2.07 ERA, Pomeranz had a 2.17 ERA across 49 ⅔ innings pitched, and Boyd made his first All-Star appearance of his career.
The Cubs recognize that signing pitchers whose value may be down could turn out to be a significant bargain for the team. It’s a strategy that the front office has sort of adopted over the last few years.
Don’t expect that to change this winter.
One pitcher that fits under that high-risk, high-reward category is former Arizona Diamondbacks starter Zac Gallen. MLB.com also highlights Gallen as one of the top high-risk, high-reward free agents this offseason.
Gallen is coming off the worst season of his career, finishing with an abysmal 4.83 ERA across 192 innings pitched. His numbers were down across the board, and most of his metrics ranked in the bottom half of the league.
So, signing him would be somewhat of a risk for the Cubs. He didn’t show he could be a top-of-the-line starting pitcher last year, and the best could be behind Gallen, who turns 31 years old in August.
On the other end of that, though, this could have just been a down year for the right-hander. He had a combined 3.20 ERA in the three seasons prior (2022 - 2024), and this is a pitcher who finished third in National League Cy Young voting just a few years ago in 2023.
That would certainly make Gallen a high-risk, high-reward signing this offseason. He has shown he can be an elite starting pitcher in the league, but a poor 2025 campaign makes him a huge question mark in free agency.
However, this is a type of move that the Cubs could be looking to make to save some money. Since Gallen posted subpar numbers this past season, his market value is definitely down heading into free agency.
MLB Trade Rumors predicts Gallen to sign a four-year, $80 million contract this offseason, while Spotrac has his market value set at four years, $74 million.
For roughly $18 to $20 million per season, the Cubs could take the risk. Gallen has the third-most innings pitched (734) in baseball since the start of the 2022 season and has had major success in this league before.