As Trade Deadline Approaches, Whom Might Chicago Cubs Look to Move?

The trade deadline is the equalizer in baseball. Regardless of your status—as a team fighting for the playoffs, or a team more excited about draft-positioning—the reality is your team is likely to be active in the leadup to July 31. That's not to say there isn't a side that's more fun to be on, and thankfully for the Chicago Cubs, it seems as though they're likely to be on the right side of things; buying. It means that your season has gone well, and in the Cubs' case, it's gone very well. But no team is perfect. The Cubs are hoping to acquire some pitching and hitting at the deadline. 

The deadline is a bit bittersweet, as well. While the Cubs may acquire a new front-line starter or a third baseman, it will mean names and players will be headed outside of the organization. For someone who spends as much time on the minor-league side of things as I do, it can be difficult to see some of your passion projects head out for a rental. But c'est la vie. I'd also like to see the team win a World Series. 

With that said, here are a few names who could end up outside of the organization. This isn't meant as a ranking list, just names I think we should familiarize ourselves with as possibilities to leave, and what they may become down the road.

1. Kevin Alcántara or Owen Caissie: 
I'm going to cheat right off the bat and say two players for one slot. I think these two are inevitably tied together, in a "one goes, one stays" type of situation. Caissie, for example, was already almost traded for Jesús Luzardo this offseason, so we have precedent for what Caissie is likely to be able to bring back. 

Either way, when the Cubs make their biggest deadline splash, I would guess one of these two names will be part of that package. There are some who have strong preferences between them, but whichever way that breaks for you, these represent their best prospects I think are likely to move. 

In terms of their upside, both offer first-division starter upside. Alcántara is a bit of a unicorn, at 6-foot-6 and capable of playing an above-average center field. Caissie, on the other hand, is beginning to flash enough power where you can squint and see 35 or more home runs from his left-handed swing. Both have enough red flags with their swing-and-miss tendencies that both could come up far short. Because both are outfielders (primarily), I do think their fate is tied with one another. I'm prepared to lose one of these in the next 31 days. In fact, I would call it an upset if they didn't.

2. Moisés Ballesteros
I don't think it's over 50% that they deal Ballesteros, but I think it's more likely than people might think, as well. The reality on Ballesteros is that his defensive value makes you question what his ceiling is, and how the Cubs view his defensive production and value will factor in. If the Cubs believe Ballesteros can start 75 games (or so) behind the dish at the MLB level, then he's probably too good to trade—barring an elite player with some team control attached. His contact ability, combined with his 20-homer power and approach, could make him a star at the position, even if he's only there half of the time. However, if you're unconvinced of the progress there, and he's likely a DH? Well, that changes the math.

I added Ballesteros here because I don't think he's entirely off-limits, if the Cubs question the defense. They called him up when they needed a DH, but found a 40-man spot for Reese McGuire when they needed a catcher. While it doesn't explain their long-term view, it says in the interim, he's not viewed as ready to catch in the big leagues. If the Cubs decide to make a big splash, I do think he could go. (The Twins, for the record, really need a new complementary catcher.)

3. Jonathon Long
Long has had a really great year, posting great Statcast data on top of being 23% better than the league average in Iowa. He maintains strong contact ability, big exit velocities, and strong walk totals. However, as a first baseman with power that likely sits between 18-25 home runs, I do question how the Cubs will view him, long-term. It wouldn't be crazy to see him as a good-not-great upside prospect and "found money". Long was just a ninth-round selection in 2023, so getting any value out of him is a win—even if that value comes via trade.

Long probably cannot headline the "big" deal, but could headline a smaller one or act as a secondary piece. There's some chance that this one hurts on the back end, if Long lands in a favorable spot and his exit velocities translate. At the same time, Long may never hit for enough power to be a great first baseman or DH. He feels likely to move, with the Cubs already stocked with plenty of bat-first guys. 

4. Christian Franklin
Much like the aforementioned Long, Franklin is probably a trade candidate due to his roster circumstances. I like Franklin, and have written about him in the past. The Statcast data looks pretty solid, he's got a wonderful plate approach, and he's mostly playable across the outfield. Upside-wise, he could be a second-division starter or a high-level fourth outfielder. But I also think that is exactly why he will be dealt; he's likely to be more valuable to another team, with contention out on the horizon. 

Again, like Long, Franklin probably is incapable of headlining any trade. He could be coupled with some sort of a low-level lottery ticket. A few years ago, the Cubs traded left-handed reliever Andrew Chafin to the Oakland Athletics in exchange for Daniel Palencia and Greg Deichmann. Deichmann looked like a low-ceiling but high-floor guy in Triple-A, and Palencia was the low-level, high-upside lottery ticket. Franklin and something like JP Wheat could bring back a solid enough reliever on the back end. I would expect that's the kind of move Franklin goes in. 

5. Riley Martin
No, I will not shut up about this guy. I've talked about him a bunch lately, both in writing here and on the podcast, but I think he's an interesting name to keep in mind in July. At 27 years old, Martin isn't young, but he fits a "late bloomer" mold. He's showing improved strikeout and walk rates in Iowa; he's probably ready for the majors. With the Cubs, he's stuck behind the Caleb Thielbar and Drew Pomeranz lefty combo, but is also probably still behind internal lefties like Jordan Wicks and Luke Little. 

Martin profiles as a mid-inning reliever, which means his trade value is probably pretty limited. However, I also expect he will be a name most teams will circle as a throw-in. His curveball is great, his fastball shape is solid, and he's basically ready to go. As a third piece in a deal or the guy you swap a rental bench piece for, you can do a lot worse than Riley Martin. The payoff isn't massive, but left-handed arms will always be in demand. I know if I were the Pirates, the A's, the Rockies, he'd be a name I'd try to sneak into a deal. 

Bonus Name: Jordan Wicks
I didn't think he was so certain that I needed to add him to this list, but Wicks feels like a name that's bound to come up. There's draft pedigree behind him, and while his MLB data can look unimpressive at times, he's made some good noise in Iowa recently and the velo has ticked up. Injuries seem to have knocked his value down. Perhaps he can be used in a trade to get a controllable arm back, or maybe the Cubs just don't want to sell at pennies on the dollar. I find Wicks an interesting name to monitor. 

What do you think, will the Cubs make a big July splash? Who do you think will be traded? Let us know in the comments below.

Interested in learning more about the Chicago Cubs' top prospects? Check out our comprehensive top prospects list that includes up-to-date stats, articles and videos about every prospect, scouting reports, and more!