The Cubs are on the hunt for rotation upgrades — a fact that’s both been widely reported and publicly confirmed by president of baseball operations Jed Hoyer. It’s easy enough to see why. Ace Justin Steele was lost for the season due to elbow surgery back in April. Shota Imanaga is returning to the rotation tomorrow, his first start since a hamstring injury sent him to the 15-day IL back on May 4. Javier Assad hasn’t pitched this year due to multiple oblique strains. Young right-hander Ben Brown was optioned to Triple-A yesterday amid ongoing struggles. Swingman Colin Rea, moved into the rotation during that injury deluge, has begun to struggle after initially excelling in a starting role.

Few teams have decided on a deadline direction yet, but Chicago has already been in contact with some clubs that know they’ll operate as sellers. Ken Rosenthal of The Athletic reports that the Cubs have inquired on Marlins right-handers Sandy Alcantara and Edward Cabrera. USA Today’s Bob Nightengale writes that the Cubs also have some interest in Pirates righty Mitch Keller (as well as closer David Bednar). He adds that they’ve kept tabs on A’s righty Luis Severino before quickly downplaying the possibility that the Athletics would actually trade the veteran right-hander in the first season of his three-year, $67MM contract.

There are surely other names on the Cubs’ radar, but the early connections are notable. That’s particularly true on the heels of 670 The Score’s Bruce Levine reporting earlier this week that the Cubs are being aggressive and are hoping to push something across the finish line well ahead of next month’s deadline — perhaps even within the next week to ten days (audio link). Levine suggested that Alcantara was not the likeliest target and that someone a bit more under the radar was more probable.

The Marlins duo stand as obvious trade candidates. Alcantara entered the season as perhaps the most plain-as-day trade candidate in the sport. The 2022 NL Cy Young winner is in his first full season back from a Tommy John procedure that cost him all of the 2024 campaign. He’s earning $17MM this year and next, and the Marlins hold a $21MM club option for the 2027 season.

Alcantara, 29, didn’t do his trade candidacy any favors early on. He pitched to an awful 8.47 ERA through the end of May, striking out only 16.9% of opponents against a 12.2% walk rate along the way. He’s since shown signs of life. Alcantara has pitched 23 innings over his past four starts and allowed a total of seven runs (2.74 ERA) on 18 hits and five walks with 19 strikeouts (20.4 K%, 5.4 BB%). His 46.4% grounder rate in that time is comfortably better than average but a ways from its 53.4% peak. His fastball velocity hasn’t been much of a question all year, averaging better than 97 mph — 97.6 mph over his past four starts. That’s down a slight bit from his 98 mph average pre-surgery, but not by an alarming measure.

If Alcantara can continue distancing himself from that bleak two-month start and continue resembling his 2022 self, the chances of a trade will only increase. Every club with even a glimmer of postseason contention would love to add the two-time All-Star with his ability to its staff, particularly when considering the relatively affordable nature of his salary under the terms of the contract extension he signed a few years back. The asking price on Alcantara figures to be steep, however, and the Marlins may wish to hold him a bit longer to allow him to continue posting improved results and further drum up interest. If that’s the case, the timing may not align with Chicago’s more urgent push for a starting pitcher.

Cabrera, 27, isn’t as well-known as his teammate but was a highly touted pitching prospect himself prior to his big league debut. He’s shown glimpses of that potential in the past, but the 2025 campaign thus far has the makings of a possible breakout. In 59 innings, Cabrera has pitched to a 3.81 ERA with a 24.8% strikeout rate, a 10.2% walk rate and a 42.9% ground-ball rate. He’s averaging a career-best 96.7 mph on his four-seamer, has ramped the usage of his sinker up to a career-high 23% and is throwing more sliders than he has in the past two seasons.

Cabrera entered the 2025 season with 2.147 years of major league service. That was enough for him to reach Super Two designation, meaning he’s already gone through the arbitration process once, coming away with a modest $1.95MM salary. He’ll be owed a raise in each of the next three offseasons before hitting free agency following the 2028 season. He’s nowhere near as established as Alcantara or Keller — Cabrera has never even pitched 100 innings in a big league season — but his power arsenal, low salary and that remaining club control hold obvious appeal.

Turning to the Pirates, Keller is a sensible enough trade candidate, even though the Bucs probably aren’t in a rush to trade him. He’s only in the second season of a five-year, $77MM contract. The former second-round pick and top prospect is earning $15MM this year, and that extension (which tacked four years and $71.6MM onto his previously agreed upon arbitration salary for 2024) calls for salaries of $16.5MM, $18MM and $20MM in the three subsequent seasons.

Keller has appeared in at least 31 games in each of the past three seasons and is on pace to do so again in 2025. He’s started 16 games and totaled 94 innings with a 4.02 ERA, an 18.5% strikeout rate, a 6.1% walk rate and a 45.5% ground-ball rate. That strikeout rate is down from 23.5% he posted in 2023-24, but Keller is getting more grounders and issuing fewer walks than in those seasons. His velocity is down about a half-mile per hour from last year, with his average four-seamer clocking in at 93.9 mph and his average sinker at 92.8 mph. Keller has made some alterations to his pitch selection, throwing his sinker less and his slider at a career-high 34.9% rate. He’s also ditched his cutter and is reincorporating a changuep that he effectively shelved for 2024.

The possibility of an intradivision trade with a player of this caliber is fascinating, if only because it rarely occurs. The Pirates are deep in pitching talent, however, with Paul Skenes anchoring the rotation and Bubba Chandler — perhaps MLB’s top pitching prospect — seemingly ready to go in Triple-A. Bailey Falter is a relative veteran at this point, and the Pirates have a deep stock of additional young arms including Mike Burrows, Braxton Ashcraft, Thomas Harrington and Hunter Barco. Jared Jones underwent Tommy John surgery this summer but looked promising as a rookie last year. Johan Oviedo was a solid fourth starter in 2023 before his own Tommy John procedure. Veteran Andrew Heaney is eating innings in the rotation right now but seems like a lock to be traded before the deadline if he’s healthy.

Whether that depth would be enough to persuade the Pirates to part with Keller is an open question. This is Ben Cherington’s sixth year as Pirates general manager, and the Bucs haven’t won more than 76 games in a season during his tenure. Trading Keller would be more akin to the large-scale rebuilding moves made earlier in his tenure, but if a trade partner were to give up immediate MLB talent, it wouldn’t necessarily indicate a step back. Dealing from a position of strength and then using the money that had been earmarked for Keller to bolster other areas of the staff could make good sense. Of course, given the Pirates’ history, it can’t be assumed that owner Bob Nutting would just pump Keller’s salary right back into the payroll by way of offseason free-agent signings or trade acquisitions.

From the Cubs’ stance, Keller or Alcantara would fit nicely into the payroll (and Cabrera even more so, of course). They’re veterans on the sort of mid-range contracts Cubs ownership seems to prefer with regard to pitchers.

The Cubs only have about $123MM in guarantees on the books next year, though that number will almost certainly rise to $138MM when the team picks up a three-year club option on Imanaga. Even still, that leaves plenty of room for Keller, Alcantara or just about any other rotation target. Assuming that Imanaga option is exercised, he and Dansby Swanson will be the only players signed beyond 2026. The Cubs obviously hope to extend Pete Crow-Armstrong and re-sign Kyle Tucker, but those goals arguably only increase the importance of finding some cost-effective ways to round out the starting staff.