Is this 2021 all over again?

As the Cubs continue down their death spiral, losing a game in which Jameson Taillon started and they only allowed 2 runs, thoughts turn back to 2021.

With all the talk of what the Cubs would be willing to give up to add a starter or a top-line reliever, no one has really started to think about assets the Cubs could decide to trade to bolster the team in 2027 and beyond.

Of course, the signing of Alex Bregman and extensions to PCA and Nico Hoerner make a tear-down of 2021 proportions impossible. But the Cubs do have several guys on the roster who could be considered trade chips if the team continues down this path to oblivion.

Is it too early to think that the Cubs might be a seller in 2026? Probably. And I don’t see any way that any of these guys are traded if the Cubs are still contending for a playoff spot when we see the deadline/ But let’s speculate on some name regardless. Here are all the Cubs who will be free agents after this season:

The Starters

• Shota Imanaga – as a player who accepted a qualifying offer, the Cubs would have to wait until June 15th to trade him, but that would not be an issue. The real issue is all of the home runs he’s given up. After his first several starts, getting him for $22 million this season looked like a steal, and I was wondering if the Cubs had made a huge mistake by not picking up the 3-year team option. Well, now that decision is looking much better, but spending the $22 Million on him instead of another starter is looking like the bad move. If he can get back his early season form, the Cubs could get something for him.
• Matthew Boyd – He’s been hurt twice this season already, so trading for him could be a risky move for a contender. But the fact that his latest injury was not to his arm, and his innings have been more limited this season, could make him more enticing on the trade market.
• Jameson Taillon – I can’t see any contender being interested in Taillon, unless he can replicate what he did against the A’s. I think a team would need to be desperate for innings from a starter to pick him up, and the cost would be pretty low.
• Colin Rea – Rea is an intriguing guy, as he’s been the Cubs’ 2nd best starter lately. Despite being almost 36, he’s been solid the last two seasons, and I could see the Cubs getting a decent prospect for him. Certainly no one in the top 10 or maybe even top 20 of a system. But perhaps a flyer on a lower rated prospect who the Cubs like.

The Releivers

• Caleb Thielbar – Any team looking for a solid 39-year-old lefty out of the pen would be interested in Thielbar. His velocity has actually been the best of his career, with a 4-seamer averaging 93.4 MPH (above his career high of 93.2 in 2024), with his Curveball and Slider actually at their highest velocity, as well. He only averaged 90.2 MPH on his fastball in his debut year of 2013, so he appears to be the Benjamin Button of pitchers. does have a mutual option for 2027, but those are almost never exercised by one side or the other. I’m guessing he could bring back a fringe prospect.
• Hunter Harvey – He might not even be healthy before the trade deadline, so I’m guessing he won’t be traded. When talking about swings and misses by the front office, he appears to be one of them. He’s another guy with a meaningless mutual option.
• Hoby Milner – He has been very effective in 2026, and is only one a 1-year deal. He’s another guy that could get back a fringy prospect. The one concern for teams looking to add him is that his FIP is 3.98 and BABIP is .214. SO the 2.33 ERA he has posted may not be sustainable.
• Jacob Webb – He was a guy I thought the Cubs might DFA in April, but he had a very strong May, and has a 1.5M club option for 2027 that I’m sure the team would exercise.
• Trent Thornton – Might bring back something in return if he can cut down on home runs allowed.

Position Players

• Ian Happ – He has a full no trade, and there’s no indication he will be willing to waive it. But he will be a free agent, and maybe he would want to move to a contended. He has been an all or nothing player this year, with more homers than expected but a ton of strikeouts. His defense in left is stellar, so he could bring back some good prospects if he was willing to waive the no-trade. An extension is still a possibility, but do not look likely right now.
• Seiya Suzuki – he is slugging only .386, and looks lost at the plate. Another player with a full no-trade, he has done very little this year to make the Cubs even think about an extension. And I would not think any teams would be looking for a streaky power hitter who has shown almost no power this season. And that’s assuming he would be willing to waive his no-trade.
• Carson Kelly – After an excellent 2025, Kelly has seen his power drop in 2026. But his OBP has improved, putting his wRC+ of 113 at almost the same number in 2025 (115). That is 9th among catchers with 150 plate appearances. Most of the teams in line for the playoffs this season have pretty good options at catcher, but an injury could drive a team to make a run at Kelly.
• Michael Conforto – I was skeptical when he was added about a week into Spring Training. But he’s hit a few huge home runs ,and has been a great bat off the bench – who should possibly be getting more starts. I don’t think he’d bring back a lot in a trade, but he could bring back something.

Overall, I think it is much more likely the the Cubs would trade multiple pitchers if they did become a seller

One of the big concerns is where this leaves the Cubs in 2027. They would certainly need to his the free agent market for a starter or two, rebuild the bullpen, and find players at the corner outfield and catcher. Assuming all the free agents leave, the team could look something like this:
SP Steele
SP Horton (not ready to start the season)
SP Brown
SP Cabrera
SP Assad
SP Free Agent
CL Palencia
RP Maton
RP Webb
RP Rolison
RP Hollowell/Little/Roberts/
RP Free Agent
RP Free Agent
RP Free Agent
LF Alcantara
CF PCA
RF Shaw
3B Bregman
SS Swanson
2B Hoerner
1B Busch
C Amaya
DH Ballesteros
IF Ramirez
OF Free agent
C Free Agent
Bench Free Agent