Looking ahead to 2027, the Chicago Cubs have a lot of work to do on their pitching front. They are poised to lose five starting pitchers and several relievers to free agency. Although the inevitable pitching overhaul will come with challenges, a silver lining is that there will be plenty of 40-man roster spots open for minor league players already within the system.
This is good since the Cubs have a crop of pitchers in the upper levels of their organization that need protection from the Rule 5 draft. Teams have until Nov. 17 to add players to the 40-man, thus protecting them from other teams. I should note that there may not even be a Rule 5 draft this year since it is tentatively scheduled for Dec. 9, eight days after the Collective Bargaining Agreement expires.
4 Cubs prospects Chicago can't afford to lose in the Rule 5 draft
So unless the Player's Union and the MLB owners come to an agreement soon (which seems unlikely), the Rule 5 draft is in jeopardy. But the 40-man roster deadline is a few weeks earlier so teams will need to make their decisions on protecting players in mid-November regardless. With all that in mind, here are four pitchers I think the Cubs need to protect.
RHP Jaxon Wiggins
It's virtually a guarantee that the Cubs will add Wiggins to the 40-man roster. Although he's been replaced as the team's best pitching prospect, he is still ranked in the top 10 in the system, and he found success as a reliever for the Iowa Cubs late last year. While the Cubs would prefer it if he could stick in their starting rotation, a relief job might be a clearer path as he seeks his major league debut.
With a fastball that can touch triple digits with his fastball and offer solid offspeed pitches, Wiggins will certainly play a role in 2027, and he may even be an Opening Day roster candidate. That is, if the team doesn't trade him in the offseason. The Cubs have several starting rotation spots to fill, and Wiggins has struggled to prove he can help in that area. There's a good chance he gets shipped out for a starter since he is one of the team's most valuable trade chips.
RHP Brody McCullough
Brody McCullough has struggled with injuries, missing all of the 2025 campaign and failing to reach more than 90 innings pitched in his career. That being said, McCullough has been great when he's healthy. Over 43 minor league games, McCullough owns a solid 3.15 ERA with 197 strikeouts, 1.07 WHIP, while opponents hit .194 against him.
McCullough worked his way back from forearm surgery he underwent last November. After returning to the mound in June, the 26 year old returned to form with a 3.27 ERA in 13 starts in 2026. The Cubs do not have a lot of starting pitching depth in their system, so McCullough is a logical 40-man addition this winter since he is in line to crack the Triple-A roster early next year.
RHP Tyler Ras
The Cubs signed Tyler Ras last January after two failed stints with the Rockies and Astros. With a mid-90s fastball, Ras quietly had one of the best minor league seasons for the Cubs last year. As a reliever for the Knoxville Smokies, Ras posted a stellar 2.13 ERA with 71 strikeouts over 67 2/3 innings pitched. He also led the team with eight saves.
Ras is a guy who will be on the Triple-A roster sooner rather than later, putting him in the major league pitching depth conversation for 2027. If he continues on this track, Ras could be the pitching lab's next reclamation project to hang their hat on.
LHP Evan Taylor
A lesser-known prospect who is Rule 5 eligible is Evan Taylor, a 26 year old reliever who reached the Triple-A level in 2026. Although he got pounded during his time with the Iowa Cubs (7.62 ERA), it was a small, 13-inning sample size that doesn't tell the whole story. Taylor posted dynamite numbers across all levels of the minor leagues before that Triple-A promotion, with a career 2.84 ERA dating back to 2022.
That includes 49 2/3 innings for the Tennessee Smokies last year, where Taylor dominated with a 2.36 ERA and 71 strikeouts. Given the sorry state of Chicago's pitching depth, this is a guy on the verge of the majors who needs to be protected.
