Is it that time already? It feels like spring training was just a few weeks ago. The July 31 trade deadline is still a while away, but that doesn’t mean that the Cubs should wait to make a move for a key player. All the players I mention in this post will be pitchers, since I believe the Cubs’ lineup is obviously very well rounded, as they’ve proved themselves to be one of, if not, the best lineup in baseball. There are definitely some teams that don’t know if they’re selling quite yet, so let’s start off with the definitive sellers.

Miami Marlins:

Sandy Alcantara

Maybe the biggest trade rumor involving the Cubs in 2025 has been a trade with the Marlins for 2022 Cy Young winner, Sandy Alcantara. It’s no secret that Sandy hasn’t looked the same since his various injuries, though. He’s sitting at an ERA of 7.89 (5.04 FIP) in 12 starts this season so far. His velocity is still there, but nothing is fooling the hitters he’s facing. A potential buy low candidate is what a lot of teams have been looking at him as, and his additional 2 years of control after 2025 make him more desirable. Still, I don’t think he would net nearly as big of a package as he would’ve gotten last offseason. The Marlins GM is very stingy, and if a package for Sandy isn’t right, he’ll have no problem holding onto him for the 2nd half hoping that he’ll bounce back and demand more prospects. People may point out that even Rick Sutcliffe had an ERA of 5.15 in his 15 starts with Cleveland before winning a Cy Young for the Cubs after being traded in June of 1984. This is a pretty similar situation, but I think in today’s world the Cubs will need to set out for an ace, even if it’s just a rental.

Other Marlins Arms:

While Sandy has the most impressive repertoire, the Marlins have a lot of young pitchers with some decent years of control that the Cubs could target. Max Meyer and Ryan Weathers are injured, so they’re off the table. Edward Cabrera anyone? I view him as a Ben Brown tier pitcher. Capable of great starts, but not consistent enough yet to be their main acquisition. Luckily, the Marlins do have a couple relievers I want to look at.

Anthony Bender

Bender has been a pretty solid middle relief guy for the Marlins this year. Nothing excellent, but a 2.05 ERA with a more concerning 3.87 FIP could leave him a target at the deadline. He’s not really striking anyone out, and his walks are very high, though. I couldn’t imagine the cubs giving up any top 15 prospect for him, despite his two years of control after this season.

Ronny Henriquez

You may remember this name from the Cubs’ series against the Marlins earlier this season. The best offense in baseball looked a little fooled at this 24 year old reliever’s stuff. His movement is great and he sports an above average fastball velocity. He definitely walks more than you would hope for (4.1 BB/9), but his strikeout numbers are so good this season, man. He’s a free agent in… 2031, though. So the Marlins might keep him to help their young core, or ask for too much in a trade. I’m struggling to even offer a top 15 prospect like Jonathon Long for Ronny, as I imagine Long could get us further in another trade. Maybe the Marlins aren’t the best trade targets for the Cubs.

Colorado Rockies:

Don’t worry, we’re not trading for any Rockies starters. I just want to highlight one reliever that has flown under the radar, and could be great matches for the Cubs’ bullpen.

Jake Bird

Bird is having a breakout season in some sorts, with his ERA plummeting from 4.50 in 2024 to 1.49 in 2025. His strikeout numbers have also taken a massive jump. Walks are manageable and his velocity is solid for his pitch mix. He doesn’t have a fastball that he uses often, and instead relies on a slider/sinker combo. This is our first good target. The improvements he’s made since spring have been monumental to his game. He’s under control for 3 more years after 2025, though, so the Rockies may ask for a good package. I don’t imagine any of the Cubs’ top 5 prospects being in the deal, but here’s something I could reasonably see being done. The Rockies desperately need infield help, and a guy like James Triantos would be a good fit. He’s definitely not a power hitter, but the Rockies need someone like him. Some may say this is an overpay since Triantos was a top 100 prospect as recently as some offseason lists. But after dropping his average from .300 in AAA in 2024 to .250 in 2025 (and landing himself on the 7 day IL), his value is dropping. I could see a 1 for 1 trade with maybe a young non top 30 lottery ticket prospect included.

Baltimore Orioles

After falling to 12 games under .500 in a semi-competitive division, it doesn’t look the O’s will see a playoff berth this year. I identified one starter and one reliever the Cubs could reasonably look at this deadline.

Tomoyuki Sugano

Sugano, 35, signed a one year deal this offseason to come to the US to pitch for the Orioles. Older than his fellow Japanese free agents, Sugano is a starting pitcher with an ERA of 3.23 in 13 starts this season. As I mentioned, he’s only under control for this year, so he shouldn’t cost anything huge. Maybe a younger prospect plus a more developed arm. I see a deal for Sugano including a package like Will Sanders + Ronny Cruz. Two draft picks from recent years, Sanders is a AAA starting pitcher that could help a rebuild decently soon. He just got promoted to AAA at 23 years old, so I would imagine unless he sets in on fire to stay there the rest of the year. Ronny Cruz is a really young 2024 3rd rounder out of high school with great bat speed and a good body and strength for a shortstop. He’s still 18 and has only played some complex league games, where he’s been nothing too special. Two top 30 prospects should get a deal done here considering Sugano’s low experience, control, and stuff numbers.

Felix Bautista

Here’s a big one. Bautista has been one of the best closers in the game since he debuted in 2022. Despite missing the entirety of 2024, he’s bounced pack pretty well into the 2025 season. Everything besides his walks have returned to normal, and he still has a fiery fastball that strikes out anyone he sees. His ERA is sitting at a solid 3.32 for a closer. You may see that and think “well Palencia’s ERA is lower! Who do we need to trade prospects for this guy?” That’s a fair question, but the Cubs’ bullpen is far from complete. A definite closer to put Hodge (when he comes back) and Palencia in other bullpen roles would do miles for the team. He still has control for 2 years after 2025, however, so it may cost a good package to get him. If the Orioles are serious about a rebuild, here’s the package I would offer to them. The headliner would be universal top 50 prospect, Moises Ballesteros. He would be their new DH assuming O’Hearn return to 1st base. I would also add in a AAA pitcher with control, whether it’s a guy like Wicks, Sanders, or even Birdsell. If it needs to be done, then you can add in the aforementioned Ronny Cruz too. There’s a lot of other prospect capital in the system’s top 15-35 that the Cubs could offer too, like the pitcher Ryan Gallagher who’s been flying up the team’s rankings. There’s really only a couple guys in the system I think are untouchable (Rojas and Wiggins), so I tried to choose players that would actively help the Orioles. Their outfield needs help, so Caissie or Alcantara could be in there in place of Ballesteros, but I feel like Moises is the most attractive piece of the three right now.

Atlanta Braves:

One more team for today, and it’s the one that I’m the most unsure about. The Braves are 9 under .500 in the toughest division in baseball, and should probably move guys with expiring contracts like Marcell Ozuna. But the Cubs don’t need a DH, so why am I bringing them up? Well there’s one guy they could look at…

Chris Sale

The reigning NL Cy Young winner is putting up another great season at 36 years old. With the option exercised, his contract expires at the end of 2026, so it’s more of a long rental than a permanent piece. AJ Smith Shawver’s recent Tommy John surgery definitely hindered the chances of Sale getting traded, but if the Braves want to cut some payroll and introduce some new players, this is a way to do so. The Cubs have room before the luxury tax to pay his $19 million AAV, so I feel like they would be the most aggressive team for him. Along with the Dodgers because of course. The package I would imagine might consist of top left fielder in Owen Caissie, a DH to replace Ozuna in Jonathon Long, and a very young pitcher in Nazier Mule. I feel like this package of blocked guys could outdo most packages other teams could reasonably offer for a 36 year old with a year and a half left on a mid sized contract.

The Waiting Game

Not every deal can be made early, though. Most teams that find themselves out a few games or more of a playoff spot in June want to wait until the last few hours before the deadline to decide if they want to sell or not. The hope for a competitor like the Cubs is that as many teams as possible succumb to losses, and the market gets flooded with teams looking to offload players. But with how many competing teams there are this year, it's looking like a seller's market, which will force competing teams like the Cubs and Dodgers to repeatedly outbid each other. This can make for some pretty horrendous overpays, but competitors will do anything if it could mean they get a better shot at the World Series. 

Arizona Diamondbacks

As of June 11th, Arizona sits one game under a .500 record, and 5.5 games out of a wild card spot. Teams have made crazier comebacks within a month and a half, so it makes sense why Arizona hasn't started a fire sale yet. They have a lot of expiring contracts on their hands, most notably, a couple key members of their pitching staff.

Zac Gallen

Although he has greatly underperformed so far in 2025, with an ERA of 5.15 and FIP of 4.89, his history of success may make him a highly touted top of rotation starter that so many teams are looking for. While he looked like a perennial Cy Young Award contender in 2022-2023, his metrics have fallen greatly since. A solid 2024 campaign followed, and 2025 hasn't been as kind to him. On top of the fact that he becomes a free agent at the end of this season, it may not cost a substantial amount in prospect capital to acquire him. Considering the number of teams his track record would attract, the Cubs would likely have to overpay a little if they wanted him. I can't imagine any of the Cubs' top 100 prospects would be included in a deal for a rental unless Zac really picks it up, though.  I feel like a prospect that would go in this deal no matter what is Jonathon Long. He's been one of the hottest hitters in all of minor league baseball this season, but the Cubs just don't have any room for him. Despite his stock at an all time high, he wouldn't get the deal done by himself. The DBacks desperately need bullpen arms, and a guy that could fill that role is AAA reliever Jack Neely. The Cubs acquired Neely in 2024's Mark Leiter Jr. deal, and barring a few major league appearances later that year, he's been sitting in AAA. He isn't lighting the world on fire, but his stuff and velocity are still there. A third piece in the deal may be necessary if the Cubs need to outbid another team, and I feel like a young positional prospect could do that. A possible match is the 19 year old international free agent signee, Derniche Valdez. Valdez showcases massive power and good speed, but not much else.  This package definitely wouldn't have gotten a deal done in the pre-season, but I hope Long's recent success can complete in before the deadline.

Merrill Kelly

Almost the complete opposite of Zac Gallen, Merrill Kelly is a 36-year-old starter also on his last year of team control. He's sporting a very solid 3.16 ERA so far, and can usually pitch at least six innings in a start. His standout performance this year was against Colorado's hitters, where he pitched 7 innings of shutout, one-hit baseball, collecting 11 strikeouts on the way. I imagine his package would be similar to Gallen's return, but with Derniche Valdez removed. I doubt the Cubs would ship better and more highly touted prospects to get both of them, even if they are setting out to get multiple starters before the deadline.

Texas Rangers

The last team I think could be a match for the Cubs are the Texas Rangers, who have massively underperformed. The Rangers have a lot of starters like Nathan Eovaldi and Jacob DeGrom who have been performing extremely well but are locked up on contracts that Texas wouldn't want to part ways with yet. This leaves perhaps one of the biggest surprise performances of 2025 with starter Tyler Mahle.

Tyler Mahle

After only pitching in 8 games in 2023 and 2024 combined, Mahle at 30-year-old has come back and pitched to an ERA of 2.34 in 14 really solid starts. He's a free agent at the end of the season too, so barring a sudden injury, he's one of the safest bets to get moved at the deadline. But Fangraphs still gives the Rangers a generous 20% chance of making the playoffs, so it's not a done deal yet. But in all likeliness, the Rangers will succumb to the Houston Astros and miss out on a wildcard spot. Who could the Rangers want in return for him? I'm sorry but Jonathon Long just fits with so many teams! He could play 1B for them, which has been an empty spot since Jake Burger has been struggling. DH is also open if Joc Pederson (.131 AVG) gets benched. I could see the Rangers getting a little greedy too and asking for an arm with control in addition to Long. Maybe Wicks could be the other piece, but his mediocre AAA stat-line isn't super appealing. Still, I wouldn't imagine that the Rangers would scoff at the chance to get Jonathon Long and an extra guy for a pitcher on an expiring contract.

Conclusion

If you asked me who I wanted the most, I would say it's Chris Sale by a landslide. But that's if he gets dealt. Plus with the number of teams needing his exact role, it would cost a lot. The most realistic fit is probably a starter on an expiring contract like Tomoyuki Sugano or Tyler Mahle. Zac Gallen has the highest ceiling, but there's no time to wait if he's going to keep underperforming. But with that being said, there's so many more options based on what teams will end up being sellers, and Jed Hoyer has made it clear that the Cubs will be rather aggressive at the deadline.