The Chicago Cubs Could Go "All-In" At The Deadline

[Matthew Lenz]

The Chicago Cubs are enjoying arguably their best season in almost a decade. Jim Bowden of The Athletic speculates that the front office isn't letting the opportunity pass them by and will be aggressive at the trade deadline.

In a questions and answers piece regarding the trade deadline, a subscriber asked about the Cubs potentially trading top prospects Owen Caissie and Kevin Alcántara to which he responds, "I get the impression the Cubs are “all-in” to win this year and will trade Caissie or Alcántara if that lands them the right pitcher(s)."

Caissie currently has a .963 OPS at Triple-A Iowa with 18 home runs resulting in a 144 wRC+. Alcántara, who had a cup of coffee in the big-leagues in 2024, has a .810 OPS at the same level with 11 home runs.

Do you think the Chicago Cubs should go all in at the trade deadline? Join the conversation in the comments!

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[We Got The Whole 9]

Said it in another thread, but I am not confident in this rotation pitching in the playoffs unless Imanaga gets back to last year's form. Even then it will be a new experience for him, though he has a lot of international exp from NPB and WBC. He would still make me nervous. They are going to need to add 2 guys and both should have vast postseason exp. I can see about half of our top 10 being moved. I'd also keep an eye on guys like Wicks, Little, Hodge as guys that can add value to a deal but will be sort of expendable depending on who they add.

 

Eovaldi, Morton, Kelly, Gallen, are some of the names I can see us connected to.

Edited July 9, 2025 by We Got The Whole 9

[Rcal10]

23 minutes ago, We Got The Whole 9 said:

Said it in another thread, but I am not confident in this rotation pitching in the playoffs unless Imanaga gets back to last year's form. Even then it will be a new experience for him, though he has a lot of international exp from NPB and WBC. He would still make me nervous. They are going to need to add 2 guys and both should have vast postseason exp. I can see about half of our top 10 being moved. I'd also keep an eye on guys like Wicks, Little, Hodge as guys that can add value to a deal but will be sort of expendable depending on who they add.

 

Eovaldi, Morton, Kelly, Gallen, are some of the names I can see us connected to.

None of those guys should be particularly expensive. All but Eovaldi are FA and the end of this year. And Eovaldi cost $25M a year for the next 2 years. TBH, I am not sure the Cubs would be interested in him because of that. If they did trade for him you could pretty much forget about the idea of signing Tucker unless they dumped someone after the season. 

[We Got The Whole 9]

12 minutes ago, Rcal10 said:

None of those guys should be particularly expensive. All but Eovaldi are FA and the end of this year. And Eovaldi cost $25M a year for the next 2 years. TBH, I am not sure the Cubs would be interested in him because of that. If they did trade for him you could pretty much forget about the idea of signing Tucker unless they dumped someone after the season. 

Happ should probably go TBH

[Rcal10]

Just now, We Got The Whole 9 said:

Happ should probably go TBH

It isn’t a baseball season if this fanbase doesn’t suggest Happ should go. 

[mul21]

 

24 minutes ago, We Got The Whole 9 said:

Happ should probably go TBH

Yes, let's get rid of this guy.  Qualified OF fWAR leaders since 2020:

Edited to correct the graphic because I'm bad at FG.

 

Edited July 9, 2025 by mul21

[squally1313]

Happ the player is fine, he's essentially who he has always been and for that production his contract is very reasonable. 

Having said that, resigning Tucker probably puts you in a spot where Suzuki or Happ has to go if you want any cash left over to make meaningful improvements in other spots, and that's before considering a big money pitcher like Eovaldi coming in this offseason. A $45m CBA number puts you at $55m under the luxury tax...with only 9 players signed. Steele is making $6.5m this year and I don't think that number can go down, so there's 15 spots left for arbitration costs, piecing back together a bullpen (Pressly, Brasier, Thielbar, and Keller are all FAs), and adding at least one high quality starter, if not two. 

We'll see where the events of the next few weeks leave the farm system, but going from Suzuki or Happ to Caissie is probably the least painful way to find what is going to be a needed $20m. 

[NorthsideAvenger]

What does "all in" look like?

For me, that means getting Skenes/Bednar from the Pirates and Suarez from the Dbacks.

[Rcal10]

7 minutes ago, NorthsideAvenger said:

What does "all in" look like?

For me, that means getting Skenes/Bednar from the Pirates and Suarez from the Dbacks.

I would think Skenes is not even an option. To me, all in would be. Cabrera or Ryan then a Suarez + either Kelly or Gallen, trade. Maybe Bednar or another pen arm. And I don’t really see them doing all this, either.  
I think another guy who might be an option would be Gore. Mainly because the Nats are in a state of flux. He would be my top target if the Nationals would consider moving him. 

Edited July 9, 2025 by Rcal10

[NorthsideAvenger]

6 minutes ago, Rcal10 said:

I would think Skenes is not even an option. To me, all in would be. Cabrera or Ryan then a Suarez + either Kelly or Gallen, trade. Maybe Bednar or another pen arm. And I don’t really see them doing all this, either.  
I think another guy who might be an option would be Gore. Mainly because the Nats are in a state of flux. He would be my top target if the Nationals would consider moving him. 

I'm just saying everybody has a different version of all in.  "All in" is just too vague for me.

[Tryptamine]

Happ still has a 105 wRC+ this year, it's not like he's Mancini a few years ago. He might seriously be the most underappreciated Cub in recent history. A pretty solid bet he finishes his career with 25 fWAR which is a really nice career. 

[Rcal10]

3 minutes ago, NorthsideAvenger said:

I'm just saying everybody has a different version of all in.  "All in" is just too vague for me.

I would guess what they are saying is no one is untouchable and the Cubs will be aggressive for anyone available. That is all in to me. 

[We Got The Whole 9]

God stop taking things as if I said anything bad about Happ. He's gonna be 31, declining in speed and athleticism, making 20 AAV, and we have internal options who deserve a real look. If you sign Tucker, he pretty clearly has to be the guy for me. Him and Taillon I would try to move.

[We Got The Whole 9]

47 minutes ago, NorthsideAvenger said:

What does "all in" look like?

For me, that means getting Skenes/Bednar from the Pirates and Suarez from the Dbacks.

Sorry but I don't even know why anyone would mention Skenes. He's in his 2nd year. The Pirates are not trading that dude to the horsefeathers Cubs. No way.

[NorthsideAvenger]

10 minutes ago, We Got The Whole 9 said:

Sorry but I don't even know why anyone would mention Skenes. He's in his 2nd year. The Pirates are not trading that dude to the horsefeathers Cubs. No way.

I was wondering what does all in mean. My all in is not the same as yours or Rcals, etc.

I know there is 0% chance of Skenes getting traded but he would be part of my all in scenario.

Basically what is the Cubs all in scenario?

 

Edited July 9, 2025 by NorthsideAvenger

[Dfan25]

The easiest way to take care of all their needs is trading with Arizona for one of Gallen / Kelly and Suarez . Both rentals , even with the expected interest from others , I don’t think it takes one of their top prospects to get that done . 
 

If they can get that deal done , they should have enough prospect capital to get another SP and reliever . 
 

Hooefully Arizona has a bad week . They are 5.5 back of the 3rd WC spot 

Edited July 9, 2025 by Dfan25

[chopsx9]

4 hours ago, NorthsideAvenger said:

 

I know there is 0% chance of Skenes getting traded but he would be part of my all in scenario.

 

 

The question is if the Cubs are all in.  There is no scenario in existence that results in Paul Skenes getting traded.  So it has no effect on whether the Cubs are all in or not because there is nothing the Cubs can do that would result in that trade.

[Layoutman]

Pray that "ALL IN" doesn't put the club into a nightmare situation where Caisse, Alcántara and Moises are traded at the deadline and then Tucker signs elsewhere.

Concerned that there has not been a trade for a pitcher completed yet. Wonder if it's the acquisition costs or the fact that some teams don't know if they are selling yet. 2 weeks ago there was chatter that a pitching deal was imminent. 

[Rcal10]

5 hours ago, Layoutman said:

Pray that "ALL IN" doesn't put the club into a nightmare situation where Caisse, Alcántara and Moises are traded at the deadline and then Tucker signs elsewhere.

Concerned that there has not been a trade for a pitcher completed yet. Wonder if it's the acquisition costs or the fact that some teams don't know if they are selling yet. 2 weeks ago there was chatter that a pitching deal was imminent. 

Honestly, if that did happen I would guess the Cubs got a controlled pitcher back, who is pretty good. That would also mean the Cubs have pretty decent money to spend elsewhere. Which could bring them Suarez or Schwarber or someone else for the everyday line up. While I wouldn’t like that scenerio, I don’t think it is that doomsday. 
I also think because of so many teams making the playoffs, teams are not deciding to sell yet. And any that are, right now are probably asking way too much. 

[Outshined_One]

One thing that I think is worth keeping in mind is the MLB Draft is this coming weekend. Last year, the Cubs drafted Cam Smith, who, while he was a bit of a unicorn, is currently in the majors. Two years ago, their pick was Matt Shaw.

The Cubs have had enough success with drafting, scouting, and developing hitters in recent memory that I wouldn't lose much sleep over them trading away guys like Alcantara, Caissie, and/or Ballesteros in a fair deal for controlled major league assets.

It's mostly a question to me of whether a team like the Nationals (Gore) or the Twins (Ryan) are willing to deal if the Cubs are truly pushing in their chips.

[NorthsideAvenger]

14 hours ago, chopsx9 said:

The question is if the Cubs are all in.  There is no scenario in existence that results in Paul Skenes getting traded.  So it has no effect on whether the Cubs are all in or not because there is nothing the Cubs can do that would result in that trade.

*sighs* Stop focusing on the Skenes part.

What I am asking is what does the Cubs All In plan look like?

 

[JunkyardWalrus]

I am pretty unfucking comfortable with Jed selling the Cubs' future to save his job.

 

[Rcal10]

1 hour ago, NorthsideAvenger said:

*sighs* Stop focusing on the Skenes part.

What I am asking is what does the Cubs All In plan look like?

 

For me,” all in” means all players are available. I don’t think it means get a particular player or players. That is too hard to figure out. But if I was to suggest players,  it would look like one of Gore, Cabrera or Ryan plus one of Gallen, Kelly or Lugo, then a bat to play 3rd and/or be a bench bat, and a pen arm. But all that would absolutely gut the system. 

[Transmogrified Tiger]

18 minutes ago, JunkyardWalrus said:

I am pretty unfucking comfortable with Jed selling the Cubs' future to save his job.

 

I wouldn't couch it as a desperation to save his job, if he makes even slight upgrades and doesn't go all in the team is favored to win the division and 90+ games, which is likely to get him extended.  But I am very leery of the idea that now is a good time for Jed to be extra aggressive, if anything given the prospect capital they've handed out in the last 12 months I think you could say it's nearly the opposite.  

[Rcal10]

6 minutes ago, Transmogrified Tiger said:

I wouldn't couch it as a desperation to save his job, if he makes even slight upgrades and doesn't go all in the team is favored to win the division and 90+ games, which is likely to get him extended.  But I am very leery of the idea that now is a good time for Jed to be extra aggressive, if anything given the prospect capital they've handed out in the last 12 months I think you could say it's nearly the opposite.  

I think he will be extended soon. I also am not afraid of losing top prospects, as long as it is for a guy or guys who have years left before hitting FA.