What will the Cubs’ pitching staff look like in two weeks?

There are only 12 days until the trade deadline, and I would suspect we will see a few major changes to the pitching staff as the Cubs make their final charge for the playoffs in August and September.

As we have seen over and over this season, any projections and plans must be taken with a big grain of salt due to the potential for injuries. But it’s not fun to try to project those things.

My inclination are that the Cubs will not trade for a starter until the offseason, but if they prove me wrong (which happens often) that changes the equation, pusing another one of the current starters into the bullpen.

Locks for August/September

• Matthew Boyd – he’s been much better lately, and while I’m not sure if he’s a great option for a playoff start, I think he will get one
• Shota Imanaga – similar to Boyd, Imanaga has been pitching better lately. He’s also a potential liability due to his propensity for allowing home runs. Still, he is a lock for the rotation over the next two months.
• Caleb Thielbar – speaking of home runs allowed, Thielbar has really struggled with this. However, with his track record, I just don’t see a situation where he is not in the bullpen down the stretch.
• Jacob Webb – He has been solid, and while I think he may have to share some of his high leverage appearances with some new acquisitions, he has continued to be a critical member of the bullpen
• Hoby Milner – it might be a bit risky to put him here, as he is still recovering from his appendectomy. But I still see him as a lock

Locks if/when healthy

• Daniel Palencia – Hopefully he’ll be back in late August, but we will see. Will they get a closer via a trade, or continue to make it mostly a committee
• Edward Cabrera – It seems like he’ll be back, but if the rotation continue to do well, where does he fit?
• Ben Brown – the biggest question mark – there will be a place for him in the bullpen if healthy, but can his neck hold up?

Currently in, but might not stay that way

• Ryan Rolison – he’s nearly a lock, but I still worry a bit about regression. And with arms to be added from trade and injury, there could be a squeeze
• Colin Rea – he could move to the bullpen, but I don’t see him going anywhere
• Javier Assad – he’s done very well as a starter, but we will see how that translates now that he’s in the bullpen full-time
• David Peterson – Minus one bad performance, he’s bee exactly what the Cubs needed.
• Jameson Taillon – He had a terrible start in his first game back from injury, but then settled down.
• Trent Thornton – He will be on the edge, especially with his recent heel injury.

Probably Out

• Gavin Hollowell – he’s shown some signs, but has never been consistent.
• Tyler Ferguson – he’s done better than I expected, but again, the Cubs will probably trade for someone better
• Aaron Civale – the latest of the disposable pitchers the Cubs have picked up. It will be an upset if he is still on the team after the trade deadline.

Wild Cards

• Riley Martin – where is he? Is he coming back?
• Justin Steele – will he come back this year? Sound like there zero chance he starts, but maybe he gets some relief innngs.
• Hunter Harvey – Sound like he might be done for 2026.

That puts 14 guys for 13 spots (until rosters expand in September) in my locks, injury returns and currently in. Buy Palencia and Brown may not be ready until September, if at all. That least 2 or 3 sports for pitchers who will be coming over via trade.

Ideal staff in August (13):
SP – Boyd
SP – Imanaga
SP – Rea
SP – Peterson
SP – Taillon
RP – Thielbar
RP – Webb
RP – Rolison
RP – Assad
RP – Milner
RP – TBD via trade
RP – TBD via trade
RP – TBD via trade / Thornton

Staff for Ideal staff in September (14):
SP – Boyd
SP – Imanaga
SP – Rea
SP – Peterson
SP – Cabrera/Taillon
RP _ Palencia
RP – Thielbar
RP – Webb
RP – Rolison
RP – Assad
RP – Milner
RP – TBD via trade
RP – TBD via trade
RP – TBD via trade / Thornton / Steele / Brown