Who Are the Cubs' Top Trade Chips This Trade Season?

It's mid-June, and the Cubs sit a game behind the Dodgers for the best record in the National League, while carrying the second-largest division lead in baseball. The bullpen has been baseball’s best for the past month and change; Pete Crow-Armstrong looks likely to receive MVP votes; and Shota Imanaga should be back from his hamstring strain soon. This should be the most fun summer in Wrigleyville since at least 2018.

With six weeks left before the trade deadline, the Cubs have two distinct options: let it ride with the current group while adding a peripheral piece or two, or go out and get an impact starter and reliever. Based on Jed Hoyer's public remarks so far, it sounds like they're leaning toward the latter. To make those moves, they’re going to have to continue to dip into their farm, which was ranked eighth in baseball before the season by mlb.com.

As it stands right now, this trade deadline is going to be one for the sellers. More teams will eventually be out of the race, or a fringe team may decide to sell, but some of those teams that were figured to be sellers might not be. The Cubs may be battling with some of their divisional foes for some of the same guys come late July. So, who do the Cubs have to offer? 

Kevin Alcántara
There is going to be a ton of buzz around Alcántara, and another outfielder (whom I will get to later). Alcántara holds the No. 4 spot on the mlb.com Cubs prospect list, and is largely seen as expendable due to the logjam in the outfield. He still sits on the back half of the top 100 prospects in baseball, despite not getting hot yet this season. His batting average is under .240, and while he does have an OPS above .700, this is not a guy who's forcing the team’s hand for playing time. His 6-foot-6 frame should give him easy pop, if he is able to cut down on his swing-and-miss. He also has 9 steals so far in 2025, and has the arm and range to stick in center field for a few years, giving “The Jaguar” a very interesting all-around profile.

Alcántara could probably fetch a mid-rotation starter or a higher-leverage reliever on an expiring contract, almost on his own. Instead of trying to flip Alcántara to a team like the Marlins, Rockies (unless we're discussing reliever Jake Bird), or White Sox, the Cubs would be better off waiting to see if teams like the Twins, Orioles, Diamondbacks or Red Sox decide to sell. 

Owen Caissie 
In terms of Cubs outfield prospects, Alcántara would be Robin, with Caissie being Superman. Caissie is currently the No. 2 Cubs prospect (No. 45 MLB prospect), and will take the top spot very soon, once Cade Horton is no longer eligible. He was the centerpiece of the Yu Darvish trade that had many Cub fans scratching their heads. Caissie does not have the center field chops that Alcántara does, but his bat is more of a sure thing, as evidenced by his .902 OPS in Iowa.

His June slash line is .396/.484/.736, with 4 homers and 6 doubles. Although he is still striking out a lot, this is a guy whose stock is soaring. Defensively, Caissie comes with a plus arm and solid range for his size, which will make him a set-and-forget corner outfielder if he pans out. He may not be winning any Gold Gloves, but that won't matter if he's hitting 30 bombs per season. Caissie would probably be in the majors right now if he was on a few different teams, and may be the next man up in Chicago if someone goes down with an injury.

Caissie is the MLB-ready prospect whom the Cubs can include to get a frontline starter or a guy with some team control. There is an issue with trading Caissie, though: What happens if Kyle Tucker walks? The Yankees missed out on Juan Soto and have money to spend. The Red Sox just cleared over $250 million from their books. The Dodgers are the Dodgers and have struggled this season with corner outfield production outside of Teoscar Hernández. This is a whole article in itself, but to summarize, I remain skeptical that Tom Ricketts or Hoyer will pony up for Tucker. I worry that they'll be outbid. If that is the case, it might be foolish to move Caissie, unless there is a “2025 or Bust” approach afoot. 

Jefferson Rojas
Rojas is another prospect sitting in the back half of the mlb.com top 100 prospect list. He is the Cubs’ top infield prospect, now that Matt Shaw is an established big-leaguer. The Cubs handed Rojas the third-highest bonus in the 2022 international market. While undersized at 5-foot-11 and 150 pounds, his bat-to-ball skills are seen as mature for his age. The 20-year-old currently has a .282 batting average, .840 OPS and 17 extra-base hits at High-A South Bend this season. Although he hasn't yet been tested in the upper minors, he has an MLB ETA of 2026.

Rojas is not your standard 20-year-old lottery ticket, with raw, unrefined skills. He has shown an ability to consistently put the bat on the ball, with a little bit of power that should only increase as he bulks up. The Cubs believe he should be able to stick at shortstop, but a transition to second is not out of the question. Paired with another player on this list, Rojas included in a trade should help the Cubs land a high-end starter with control left after this season. With Dansby Swanson anchored at short (for now), Nico Hoerner under contract for another season, and Shaw capable of playing the middle infield, Rojas is a perfect trade chip. 

The Other Guys
James Triantos (#6), Jonathon Long (#12) and Ben Cowles (#22) are all hitters in Triple-A who don't have a path to playing time on the current roster. Long has enjoyed a breakout season, while Triantos and Cowles have not generated much hype with their play so far. These are the guys you can dangle to teams like the White Sox, Rockies and Marlins for a reliever or two.

Of course, none of those teams have a healthy, thriving player they're likely to be willing to move—other than Sandy Alcántara. His name will dominate trade rumors for the foreseeable future, and whenever he gets tied to the Cubs, keep the above set of names in mind. At least one or two of them will be involved if Hoyer decides to pounce and bring in the hard-throwing Alcántara.