The Cubs sit with a record of 56-75 with 31 games left to play this season.

Conventional wisdom would indicate a team with that record would have flexibility and a lot of potential openings on the roster.

The Cubs, however, have a lot of tough decisions to make this offseason.

A couple weeks after the World Series ends in November, teams around the league will be required to add players to the 40-man roster to protect them from the Rule 5 Draft (which typically takes place in December on the final day of Winter Meetings).

That’s where things are going to get tricky for the Cubs, who have a lot of intriguing young players that they need to add to the 40-man roster this winter or risk losing them to another organization.

“We’re having a lot of talks right now about what do we do in September kind of roster-wide and it’s complicated in a good way,” Jed Hoyer said last week. “We have a number of players we know have to go on the 40-man roster. We also just have a very big group that are eligible and we have to think through the right strategy for how we’re going to handle call-ups in September.

“It’s a little different. We’re a lot deeper farm system wise than we have been in the past and so we have to think through that as we make those decisions.”

Those decisions include who to call up as rosters expand to 28 for September. On the first day of the month Thursday, the team recalled infielder David Bote and selected the contract of reliever Jeremiah Estrada (Wade Miley was transferred to the 60-day IL to make room for Estrada on the 40-man roster).

As the month moves along, if the Cubs are going to get a look at a position player prospect in the majors, they’re more likely to call up somebody already on the 40-man roster than a player who is not (and does not need to be added this winter).

Alexander Canario has enjoyed a breakout campaign in the minors (31 homers, 21 stolen bases, .874 OPS) and can play all three outfield spots. He was just promoted to Triple-A Iowa last week but he is already on the 40-man roster and the Cubs could conceivably call him up to the majors to get some looks late in the year.

Meanwhile, Matt Mervis has absolutely raked this season. He began the year with Advanced Class-A South Bend, carried it to Double-A and has not slowed down with Triple-A Iowa (.294 AVG, .925 OPS). In total, Mervis has 27 homers, 36 doubles, 100 RBI and a .971 OPS this season as a 24-year-old.

Mervis’ left-handed bat and power could be an asset to the Cubs in the majors for the final month of the season with expanded rosters, especially since he plays first base and the team just put Patrick Wisdom on the IL last week.

But Mervis does not need to be protected on the 40-man roster this winter and the Cubs have plenty of other players who do. And while Mervis has had success in Triple-A this season, his 33-game workload there isn’t a super long track record and he could benefit from more seasoning at the upper levels of the minors.

“There’s always a fine balance between letting guys be at a level for a whole year and be comfortable,” Hoyer said earlier this month. “Some guys you want to do that with. I think that’s important. And then other guys you want to continue to challenge.”

On top of all the internal candidates for the 40-man roster this winter, Hoyer has also said the Cubs plan to be active in free agency this winter.

Let’s dive more into the roster crunch as it stands right now.

Here is the list of players scheduled to become free agents (and thus removed from the Cubs’ 40-man roster):

1. Willson Contreras
2. Wade Miley
3. Drew Smyly (has a mutual option for 2023)
4. Jason Heyward (team will release him after 2022 season)

Of course, the door is not closed on Contreras, Miley or Smyly — the Cubs could always opt to bring any of them back for 2023.

Here are the players who are currently on the 40-man roster and are locks (or close to it) to stay on the roster to begin the offseason:

1. Nico Hoerner
2. Seiya Suzuki
3. Ian Happ
4. Nick Madrigal
5. Christopher Morel
6. Yan Gomes
7. P.J. Higgins
8. Nelson Velázquez
9. Marcus Stroman
10. Justin Steele
11. Keegan Thompson
12. Javier Assad
13. Brandon Hughes
14. Manny Rodríguez
15. Erich Uelmen
16. Patrick Wisdom
17. Rowan Wick
18. Michael Rucker
19. Alexander Canario
20. Caleb Kilian
21. Brailyn Marquez
22. Nicholas Padilla
23. Miguel Amaya
24. Jeremiah Estrada

Of course, the Cubs could surprise and move on from any of these players to create room on the roster, but the players on this list are generally expected to contribute to the team next year.

Then there are a bunch of injured players who are on the 60-day IL (and thus technically not on the 40-man roster at the moment) who are expected to remain on the roster this winter even if they don’t return this season:

25. Kyle Hendricks
26. Adbert Alzolay
27. Codi Heuer
28. Ethan Roberts
29. Brad Wieck

Note: Heuer, Roberts and Wieck all underwent Tommy John surgery this year and are expected to miss most — or all — of 2023. MLB teams are not allowed to keep players on the 60-day IL during the offseason so the Cubs would need to use 40-man roster spots on all three pitchers. 

There is also a pretty big group of players who are currently on the 40-man roster and definitely options to remain with the team but might be on the bubble (for one reason or another):

30. Zach McKinstry
31. Mark Leiter Jr.
32. Alfonso Rivas
33. Franmil Reyes (will be in Year 2 of arbitration)
34. Rafael Ortega
35. Sean Newcomb
36. Michael Hermosillo (60-day IL)
37. Alec Mills (60-day IL)
38. Adrian Sampson
39. Frank Schwindel
40. David Bote
41. Narciso Crook
42. Kervin Castro
43. Alexander Vizcaíno (has been on restricted list since March)
44. Steven Brault
45. Anderson Espinoza
46. Luke Farrell

Many of these players have performed well with the team when they have received opportunities but could be caught up in the numbers game.

The Cubs thought enough of Reyes and McKinstry to acquire both in August via waivers and a trade, respectively, and both have been solid contributors — albeit in a small sample size. It’s very possible — likely, even — that they are bumped up into the “locks” section of the roster by the end of the 2022 regular season.

Now, this is where things get tricky. The Cubs already would have to make 6 cuts to begin the offseason and trim the roster to 40 and they also have upwards of 25 minor league prospects that are eligible for the Rule 5 Draft.

Some of those prospects are locks to be added — Brennen Davis, Ben Brown, Hayden Wesneski and Kevin Alcantara.

Hayden Wesneski has a 0.60 ERA over his last three outings with the @IowaCubs.

🔥 15 IP
🔥 15 K
🔥 4 H
🔥 1 ER pic.twitter.com/76NGoVnCFv

— Marquee Sports Network (@WatchMarquee) September 1, 2022

But there are a bunch of other minor leaguers whose cases aren’t quite as cut-and-dry. Will the Cubs add them to the 40-man roster or risk losing them to another MLB organization?

That list includes (but is not limited to):

LHP Brendon Little (who was up in Toronto as a replacement player)
OF Darius Hill
RHP Cam Sanders
RHP Cayne Ueckert
RHP Danis Correa
1B Bryce Ball
INF Chase Strumpf
RHP Ryan Jensen
RHP Riley Thompson
RHP Kohl Franklin
OF Yohendrick Piñango

Plus a host of others.

Simply put, the Cubs won’t have room for everybody.

“It’s a good problem to have,” Hoyer said. “There’s years we haven’t had this problem and when you don’t have that problem, you’re well aware that it means you’re probably not deep enough in the minor leagues. We have a lot of depth so we are going to have some really hard decisions to make.”

The Cubs won’t have to answer all of these questions right now and the final few weeks of the season in both the majors and minors can help provide clarity. But this will definitely be an interesting storyline to follow in the first few weeks of the MLB offseason.