Cubs Rule 5 Draft Primer: Time, Date, And 3 Players Chicago Might Select

[Jason Ross]

Image courtesy of © Kim Klement Neitzel-Imagn Images

Major League Baseball is full of oddities, and the Rule 5 draft feels like a convergence of many of them, as players are not always eligible at the same ages or what even feels like the same stages of their careers. It's a leveling ground of underrated, maybe-too-young for prime-time International Free Agents, over-the-hill former prospects, and middle-round picks mixed between. It's a time for MLB organizations to gamble and find talent that another team has overlooked. While the Rule 5 draft can feel like an afterthought, coming on the last full day of the MLB Winter Meetings every year, it's a day of hope for many players looking to get their shot in the big leagues.

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When: Wednesday, December 10, 2025 @ 2pm ET
Players the Cubs may lose: SS Cristian Hernandez, SP Brandon Birdsell (injured), SP Grant Kipp, SP Connor Noland

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Recent Cub Rule 5 draft picks include:

• 2024: Gage Workman, INF (Detroit Tigers)
• 2020: Gray Fenter, P (Baltimore Orioles)
• 2019: Trevor Megill, P (San Diego Padres)

The first two names on this list, Gage Workman and Gray Fetner are fairly inconsequential names; neither was any good with the Cubs and neither have settled in anywhere else. Workman posted a 38 wRC+ between both Chicago clubs before finding his way back to the Tigers organization for whom he performed well (for an older guy) at Triple-A. Fetner, who never made an appearance for the Cubs, has been out of Major League Baseball since 2023 after flaming out with the Yankees. As with most Rule 5 picks, they rarely pan out.

Trevor Megill, however, has come back to haunt the Cubs a bit. Despite not making the Cubs directly in 2020, a deal was worked out between San Diego and Chicago for the reliever to remain a Cub. Megill got his chance in 2021 with the North Siders but struggled in his 23.0 IP with an ERA above 8.00, prompting the Cubs to allow Megill to leave the organization at the end of the season. Since then, he has turned into a dominant option for the Milwaukee Brewers, pitching against the Cubs in the playoffs and shutting down opponents left and right. While most picks are like Gage Workman or Gray Fetner, there are enough Trevor Megill-types who succeed (Hector Rondon, who would pitch almost 300 innings with the Cubs and even served as their closer for a time, was a Rule 5 pick in 2012) that this can be a sneaky way to add value. 

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What might the Cubs do in 2025?
Most years, the team does not make a selection. Because you need an open 40-man roster spot to begin with and then need to be willing to carry said-draft-pick for entirety of the season for them to remain within the organization, many teams just do not have the roster flexibility to make picks. On top of that, Rule 5 picks are available for a reason. They have some warts to them; a prospect without warts would be protected from this fate, making it hard for contending teams to see the reward beyond the risk. With the Cubs currently having plenty of open space on their 40-man roster and a clear need to rebuild their bullpen, it's fair to expect the Cubs will make a selection in the Rule 5 draft this year, with that pick likely coming from the pitching side of things. Who, then, might fit what they're looking for?

Option #1: RJ Petit, P (Detroit Tigers)
RJ Petit might have a second career as an NFL lineman, as he is currently listed at a massive 6'8 and 300 pounds. Beyond just the novelty of his size, there's a bit of a dude here, as the reliever was in the 98th (or better) percentile in the following categories: xwOBA against, average EV against, hard-hit%, whiff %, called strike% and K%. His walk rate wasn't great, but still sat at 10.4%. He sits mid-90's and has a good slider and a changeup that grades out well using TJ Nestico's tjStuff+ grades. For a team who is clearly looking to add swing and miss to their 'pen, Petit fits the mold. Plus, because I'm always biased towards a good mustache, Petit is rocking an 80-grade lip-curtain. The hulking righty would be near the top of my personal wish list. 

Option #2 - Samy Natera Jr, LHP (Los Angeles Angels) 
Grabbing pitchers out of organizations with poor reputations for pitching is a good gamble, and why I think Samy Natera Jr. could end up being a player the Cubs hone in on. Natera is a tall, 6'4 left-handed pitcher with big swing-and-miss stuff who has a tendency to walk far too many hitters. So, while the reliever flashes impressive strikeout numbers, punching out 34% of opposing hitters, he also gives a lot of that back by walking 16% as well. 

Netera Jr. may fit the Cubs program, though. With it looking like both Caleb Thielbar and Drew Pomeranz will be departing the organization, their is a clear need for plenty of lefties in the Cubs' 2026 bullpen. Natera Jr. offers a strong cut-ride fastball, a pitch shape the Cubs enjoy (they cut their fastball more than any other organization in the minors), and they may think they can fix his walk issues internally. He might not survive the MLB cuts in camp, but he could be a worthwhile gamble if they believe in the raw stuff.

Option #3 - Peyton Pallette, RHP (Chicago White Sox)
Peyton Pallette falls into the "former-top-draft pick" territory we see at times in the Rule 5 draft, as he was once a second-round pick of the South Siders. The RHP's best offering is a curveball, and he has a developing slider and a decent enough fastball that you can see the beginnings of a useful MLB reliever. Because he's off-speed heavy, he doesn't throw a lot of strikes, though he generates a good amount of chase to offset that.

As he jumps up a level, he may not ever throw enough strikes, and he may struggle with walks. But he did have a 98th-percentile whiff rate, so there's definitely a real reason to believe in the strikeout capability of the former second-rounder. Perhaps a jump to a better organization (sensing a theme?) could help squeeze a few more strikes out of the breaking-ball specialist. 

Honorable Mention: Tyler Stuart, RHP (Washington Nationals)
Tyler Stuart is yet another team from an organization I don't really trust to develop players well, but I kept him in the HM category for one important reason: he's not going to pitch in 2026 as he recovers from Tommy John surgery throughout the year. A team can still select him, but they would have to carry him on the 40-man roster until the start of the season when they could transfer him to the 60-man IL, locking up a useful slot for months. Then the team would need to keep him on the active roster for 90 days the following year. A contending team like the Cubs may find that a big ask for an unproven pitcher.

However, Stuart does offer some fun upside, as he puts all of his 6'9 frame to use. The right-handed pitcher has piled up the strikeouts across the board and while his control comes and goes, a move to the bullpen could squeeze a little added juice and maybe could help him rein in his control a bit more. Players with his size tend to struggle to repeat a motion, so while he won't pitch next year, he could be a tantalizing member of a bullpen in 2027 if you have the patience (and roster space) to help him develop with MLB coaching.

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What do you think the team will do in the Rule 5 draft? Will they pick someone? Punt the pick? Or maybe there's a name I didn't cover? Sound off in the comment section below and let's start a discussion! 

 

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[CaliforniaRaisin]

The guys I’d eye for the Cubs are RHP Blake Burkhalter (Braves) or RHP José Rodríguez (Dodgers). Both would be relievers.

[Jason Ross]

2 hours ago, CaliforniaRaisin said:

The guys I’d eye for the Cubs are RHP Blake Burkhalter (Braves) or RHP José Rodríguez (Dodgers). Both would be relievers.

There's a lot of really interesting BP-style arms out there. I had those names on my radar as well. Sadly, neither can compete with RJ Petit in the facial hair department and that's an important part of my "reliever scouting report". I know my blindspots.

[CaliforniaRaisin]

 

[Jason Ross]

6 minutes ago, CaliforniaRaisin said:

 

But I want him...

[CaliforniaRaisin]

 

[CaliforniaRaisin]

 

Cubs passed. Really shocked, Burkhalter’s fastball seemed so Cubs-coded.

[Jason Ross]

1 minute ago, CaliforniaRaisin said:

 

Cubs passed. Really shocked, Burkhalter’s fastball seemed so Cubs-coded.

That is shocking. Their 40-man has the most open slots in the entire league. I guess they're planning on adding that many players?

[Bertz]

Would also indicate the plan with the bullpen is not as spartan as what Trueblood heard.  If the plan is going into March with ~4 spots filled and then just throwing out a small army of relievers in ST to compete for the last four there's no reason not to take a live arm here and just cross your fingers and hope he learns to throw strikes in the next four months.

[Jason Ross]

6 minutes ago, Bertz said:

Would also indicate the plan with the bullpen is not as spartan as what Trueblood heard.  If the plan is going into March with ~4 spots filled and then just throwing out a small army of relievers in ST to compete for the last four there's no reason not to take a live arm here and just cross your fingers and hope he learns to throw strikes in the next four months.

Absolutely. Which I'm fine with. As much as I trust the Cubs pitching infrastructure, it'd be nice if we didn't have to build the plane midflight this year.

[Bertz]

Also I'm not going to complain but some team should have popped Connor Noland.  Not having minor league options obviously kills a lot of his appeal but looking at what teams like the White Sox and A's have on hand SP wise and I feel like Noland would lift a few teams' pitching staffs.

[CaliforniaRaisin]

Cubs didn’t lose anyone in either phase of the Rule 5 draft: