The Chicago Cubs have ticked off all the boxes when it comes to the intangibles often associated with a championship team.
In terms of team character, they’ve shown persistence, true grit, and a tenacious self-confidence not seen on the North Side since the “We never quit” 2016 Cubs brought home the first World Series title in 108 years.
On the field, the offense has been the driving force behind a successful and exciting 2025. It seems that just about all of the team’s starting position players this season are either having a breakthrough year or , in the case of Kyle Tucker, a business-as-usual outstanding year. Already an established offensive powerhouse, this version of the Cubs can beat teams with speed or power and sometimes lots of both.
The Cubs bullpen has also been a surprise success story, with manager Craig Counsell and staff helping turn a ragtag group of mostly castoffs and unproven assets into one of the better pens in baseball.
Even the starting rotation, which has been battered with season-snuffing injuries to Justin Steele and Javier Assad and substantial IL stints for Shota Imanaga and Jameson Taillon, has been surprisingly tenacious in keeping itself together and reasonably competitive.
Reality trumps magic ahead of trade deadline
All of that is great, but reality tends to trump magic as the season drags on and strains of a heated pennant race start to take affect. And things only get more real once in postseason play.
So, as was the case with the magical 2016 Cubs, Chicago’s front office will need to add some key elements before the trade deadline to make sure the team is postseason-strong.
In the case of this 2025 team, the need is starting pitching– preferably a front-of-rotation piece and an inning-eating back-of-rotation arm. A bullpen asset, with closer capabilities as insurance for Daniel Palencia would also be a welcomed addition. Then, there’s the need for a bench piece, with third base and/or outfield capabilities, to improve the team’s all-round depth.
That’s a tall order for one shopping spree prior to the July 31 deadline, especially since this year’s market looks likely to be a seller’s market.
Chicago Cubs will be “all-in” at the trade deadline
Former MLB general manager and current MLB insider Jim Bowden, however, feels that the Cubs will be “all-in” when it comes to acquiring the assets they need to win this year.
Per Bowden, in a piece for The Athletic:
“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’s name in particular has come up a lot in my conversations and texts with front office execs in both leagues.”
The interesting question that will be answered by Cubs president of baseball operations Jed Hoyer in the coming days is “how much?” How much will the Cubs be willing to give up for a shot at winning a championship this year?
Trade capital
Universally listed as the Cubs top trade bait is outfielder Owen Caissie, the no. 1 prospect in the organization. The other top outfield prospect, Kevin Alcantara, also has value as a trade piece, although a recent leg injury may lessen his appeal a bit. Both Caissie and Alcantara, however, have been red hot for the Triple-A Iowa Cubs. It’s believed that at least one of these two is guaranteed gone at the deadline, with the other sticking around as corner outfield insurance in case Kyle Tucker disappears into free agency.
Pitching prospect Jaxon Wiggins has also been mentioned a lot in trade rumors. The 23-year-old Wiggins is the Cubs’ no. 8 prospect, their no. 2 pitching prospect, and is regarded as having real front-of-rotation MLB upside. Wiggins could be gone in any deal for a high-end starter with team control (no 3-month rental).
A somewhat under-the-radar trade candidate is first baseman Jonathon Long, who has been having a killer offensive year for the Iowa Cubs, but is behind another young first baseman having a killer year at the major league level, Michael Busch. Long is not only valuable as a trade piece, but also expendable.
Then, there are names such as Moises Ballesteros and James Triantos, who have value as trade capital, but who could also have value to the major league team when guys like Seiya Suzuki and Nico Hoerner become free agents after next season.
There’s also the distinct possibility that on-the-cusp big league names such as Matt Shaw and Ben Brown could be dealt.
If the Cubs wanted to, they could open the vault and deal away a good number of their prospects, trading their long-term future for their immediate future. Their current major league roster is young enough to maintain success for some years to come without an influx of talent from Triple-A.
Is that something Hoyer would do, given the risk involved in bartering present for future?
Maybe.
As we all saw back in 2021, when he pretty much traded away the whole team, the man is not shy about making big, bold moves.
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