The Cubs are heading toward a winter where the 40-man roster should open up, but that doesn’t mean they can afford to be casual about what they protect. With five starting pitchers and several relievers set to hit free agency looking ahead to 2027, Chicago will eventually need a full pitching reset. For now, though, that looming turnover creates a practical benefit: there should be room to shield some of the minor league arms already in the system.
That matters because the Rule 5 draft is approaching, at least on paper. Teams have until Nov. 17 to add eligible players to the 40-man roster and keep them out of the draft pool, though the draft itself may not even happen this year.
It is tentatively set for Dec. 9, eight days after the Collective Bargaining Agreement expires, which puts the whole process in jeopardy. Still, the roster deadline is real, and the Cubs have a few pitchers who need to be accounted for.
The clearest case is right-hander Jaxon Wiggins. He’s no longer the organization’s top pitching prospect, but he remains in the system’s top 10 and made a strong impression as a reliever for the Iowa Cubs late last year.
The Cubs would rather keep him stretched out as a starter, yet a bullpen role may be the more realistic route to his big league debut. Wiggins has a fastball that can touch triple digits and pairs it with solid offspeed stuff, which is why he could matter as soon as 2027.
He might even be in the mix for Opening Day, unless the Cubs decide to move him this offseason. With so many rotation spots in flux, he could also become one of the club’s most attractive trade pieces.
Another name worth protecting is Brody McCullough. Injuries have slowed him down badly - he missed all of 2025 and has never thrown more than 90 innings in a season - but when he has been on the mound, the results have been strong.
In 43 minor league games, McCullough has a 3.15 ERA, 197 strikeouts, a 1.07 WHIP and a .194 opponent batting average. He worked back from forearm surgery last November and returned in June, then turned in a 3.27 ERA in 13 starts in 2026.
Given the Cubs’ lack of starting pitching depth, he looks like a sensible 40-man addition and a player who should be near Triple-A early next year.
Tyler Ras also fits the profile of a pitcher the Cubs should not leave exposed. Chicago signed him last January after he had two unsuccessful runs with the Rockies and Astros, and he rewarded that move with a strong season in the minors.
Working out of the bullpen for Knoxville, Ras put up a 2.13 ERA with 71 strikeouts over 67 2/3 innings and led the team with eight saves. He works with a mid-90s fastball and is on track to reach Triple-A before long, which puts him into the conversation for major league pitching depth in 2027.
If his progress continues, he could become the pitching lab’s next success story.
The final name is left-hander Evan Taylor, a less-heralded but still important Rule 5 eligible arm. Taylor reached Triple-A in 2026, and while his time with Iowa was rough - a 7.62 ERA in 13 innings - that small sample doesn’t erase the bigger body of work.
Since 2022, he has posted a 2.84 ERA in the minors overall. Last year with Tennessee, Taylor was excellent, finishing with a 2.36 ERA and 71 strikeouts across 49 2/3 innings.
With Chicago’s pitching depth in the shape it’s in, Taylor looks like another arm on the verge who needs to stay in the organization.
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Former Cubs Prospect Offers A Warning As Kevin Alcantara Decision Looms
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That matters now because Kevin Alcantara is approaching his own crossroads, and his situation comes with real roster pressure. Alcantara no longer has minor-league options, which complicates the Cubs flexibility and keeps a trade in the conversation as teams weigh whether he can fit on a big-league roster right away. Velzquezs trajectory shows how fast a young power bat can go from prospect buzz to uncertain fit, and it leaves the Cubs with one more decision they cant afford to get wrong. [Read more 🡒]