Cubs Way-Too-Early Trade Deadline Primer: All the Targets You Should Familiarize Yourself With

It may seem like wishful thinking for the Chicago Cubs to be buyers at this point, but a lot can change between now and the trade deadline on August 3. Pete Crow-Armstrong's bat is starting to heat up since he’s been moved to the leadoff spot. Ian Happ is barreling toward his first 30 home run campaign of his career. Edward Cabrera and Matthew Boyd are (or nearly are) back. Though they have had their struggles this year, they were some of the team’s better projected options coming into the season. Plus, this is a team that made the playoffs a season ago with many of the same key players intact. They’re still over .500, and until they fall well below that mark, you can bet that the front office will not punt on the season. Though the Brewers have once again proved to be the class of the NL Central, the rest of the division is imperfect and could conceivably be steamrolled by this Cubs team... albeit when everything is clicking. 

The Cubs need to target pitching, some more pitching, and probably an extra pitcher or two just to be safe. Even with the return of Cabrera and Boyd, and the emergence of Ben Brown, they will likely need two dependable starting pitchers. Every contender shops for relievers at the deadline, but the Cubs need about half a bullpen’s worth of them. Southpaws Hoby Milner and Ryan Rolison have been serviceable, but they, combined with the 39-year-old Caleb Thielbar (who has spent time on the IL already), cannot be the top lefty options in the postseason. Daniel Palencia looks great when he pitches, but he has dealt with injuries this year and it looks like Counsell is hesitant to use him too much. Ethan Roberts and Jacob Webb have pitched well from an ERA standpoint, but they aren’t high-leverage guys. The “big” free-agent addition, Phil Maton, has an ERA over seven. If the Cubs intend to make a deep run in the postseason, they probably need another two or even three relievers, with at least one being a bankable high leverage option. 

On the offensive side, they need to improve internally because there isn’t anywhere to play a new bat unless they want to get really creative. You may see a utility player or a bench bat join the squad, but the Cubs won’t be in on any of the big-name bats on the market. Here are some of the names being mentioned in rumors you won’t see on the list below: Gleyber Torres, Mike Trout, Luis Arraez, C.J. Abrams, Jarren Duran, Byron Buxton, Ryan Jeffers, or any of the Astros’ bats.

Chicago Cubs Top Trade Deadline Targets

Without further ado, let's get into the players the front office is most likely to (or should be planning to) target this trade season.

The Grand Prize: Tarik Skubal

Skubal’s return from his loose bodies procedure is seemingly going to happen sooner rather than later, but the Tigers have been one of baseball’s worst teams and are sitting in the cellar of the AL Central. Even the two-time reigning AL Cy Young winner is not going to help this team unless he starts every other game. Skubal is also an impending free agent, and he will certainly test the market to attempt to earn the largest contract for a free-agent pitcher in MLB history. Other teams can easily strong-arm the Tigers into moving him, since they aren’t contending and don’t seem to have much of a shot at re-signing him. It would be in the best interest of the team to move him, but they won’t get anything close to the return they could have gotten if he was moved before the season. If we see the Cubs revert to their April ways on offense, there are no excuses as to why they shouldn’t be right in the middle of the Skubal conversations. The Tigers might ask for Shaw or Ballesteros as the headliner, but that’s just the price of doing business. Again, Skubal is only a feasible target if the Cubs start hitting like one of the best in baseball again and have a clear path to the playoffs.

The Big Fish: Starters & Relievers

Freddy Peralta 

While it’s not out of the realm of possibilities for the Mets to gain ground in the wild-card race, they are currently at the bottom of the division and a whopping 15 games behind the Braves. Should Peralta, who is another impending free agent, become available, he would be the number two option on the market after Skubal. The 30-year-old has been more good than great this season with a 3.80 xERA, accumulating 1.0 fWAR over 13 starts. The Cubs should be able to acquire Peralta without moving anyone off their major-league roster, but Jefferson Rojas, or last year’s first-round pick Ethan Conrad, could be on the table. 

Reid Detmers

The Angels have been one of the worst teams in baseball, but they never want to embrace a full rebuild. Their M.O. for the past decade and a half has been to get Mike Trout to the playoffs, but that goal seems as far away as it’s ever been. Detmers is currently in his second year of arbitration while making a modest $2.6 million (and, as a Super Two player, he has two more years of team control remaining). He is now back in the rotation after spending all of last season in the bullpen. His xERA is 2.92 and he’s accumulated 2.2 fWAR. He ranks fifth in the AL in strikeouts with 88 across 74 innings. If the Cubs continue to meddle in mediocrity this season, Detmers is a great addition for the future. If they bounce back, he is a great addition for right now. The Angels should be listening on Detmers, but his contract status gives them a ton of leverage in negotiations. 

Joe Ryan

The Cubs have been a logical landing spot for Ryan for some time now, but Minnesota did not want to waive the white flag yet. After a hot start to 2026, the Twins have faded as anticipated, and should be open for business. Byron Buxton and Ryan are their biggest trade chips, and should both be in high demand this summer. Ryan is having an excellent year where he has firmly taken over the best pitcher in the Twin Cities title with Pablo Lopez out for the year; he has a 3.06 xERA and 84 strikeouts. Eight of his 14 starts have been quality starts, and he has already reached 2.1 fWAR. Ryan would be the right-handed starter the Cubs desperately need, but if the Twins view Ballesteros as a catcher long term, that might be their non-negotiable ask, because their current starting catcher Ryan Jeffers could also be out the door. 

Antonio Senzatela

Senzatela was one of the more consistent Rockies starters since he broke into the league in 2017, but dealt with injuries after signing a five-year extension, completely breaking down last season with a 6.97 xERA in 30 games (23 starts). He’s made the transition to the bullpen this year and is finding success with a 3.05 xERA over 36.1 innings. The right-hander is posting the highest K/9 of his career at 7.43, and will certainly be one of the most available relievers this July. He comes with a club option for next season too, which is an added bonus. Senzatela isn’t going to single-handedly fix the Cubs' bullpen, but would be a perfect secondary move if they take a bigger swing on one of these next names. 

Aroldis Chapman

This would be a real fun move. Ten years after the Cubs acquired Chapman from the Yankees, he once again fits their needs almost perfectly. With the American League in shambles as a whole, it is far from certain that Boston is going to sell, but if they do, Chapman would be their most in-demand trade chip. The 38-year-old is showing no signs of slowing down, and has cemented himself back in the best reliever in baseball conversation. He has a 0.46 ERA in 19.2 innings while striking out 26. Should he reach 40 innings pitched, a mutual option worth $13 million would kick in for 2027. Who knows if a reunion is on the table all these years later, but it would make for a fun storyline to follow.

Josh Hader 

Houston may decide to sell at the deadline, which, like Boston, is far from a certainty; it would be marking their first deadline as sellers since the 2016 season. The hot names on the market are SS Jeremy Pena, 1B Christian Walker, and 3B Isaac Parades (with some light mentioning of MVP candidate Yordan Alvarez). The reason why Hader hasn’t been mentioned as much as those other guys is because he just started the season earlier this month. Left bicep tendinitis caused him to miss April and May, and upon returning, he has thrown two scoreless frames so far. Hader is currently in the third year of a five year, $95 million contract that represents the largest present-day value for a reliever ever. The Cubs will have some money coming off the books after this season with Jameson Taillon, Shota Imanaga, Seiya Suzuki and Ian Happ all entering free agency. It's likely they try to bring back either or both of Suzuki and Happ, but the pitchers should be gone. Using some of that money to reunite Hader with his first big-league skipper would be a move for both the present and future.

Sandy Alcantara

In my opinion, the Cubs should stay far away from Alcantara negotiations unless the Marlins would give him away for a few ballpark hot dogs, but he has been one of the more talked about trade candidates of the last few seasons, so I wouldn’t be doing my job if he didn’t get a mention. The 2022 NL Cy Young winner is on the last season of a five-year extension, but there is a club option for next season worth $21 million. Alcantara has made 14 starts this season and has allowed two or less earned runs in eight of them. He also has four starts where he has given up six or more runs. His xERA on the season is 4.05 and he has been worth 1.3 fWAR, but the Marlins have been reluctant to trade him to this point, and it might not make sense for the Cubs to meet a high asking price for a guy who blows up this frequently. 

The Role Players: Lesser Pitchers

Robbie Ray

Buster POBO-sey and the Giants seem to be punting on this season already after they fell flat on their face early on. Starting catcher Patrick Bailey was already moved to Cleveland in a rare May trade. They’ve also announced a willingness to move SS Willy Adames, 3B Matt Chapman and OF Jung-Hoo Lee. Don't doubt that they would be happy to move the 34-year-old Ray as well, as he is in his last year of the five-year deal he signed with the Mariners after the 2021 season. The 2021 AL Cy Young winner is not having a great campaign, but at least he is healthy and making his starts. The 4.12 ERA and 1.40 WHIP is not going to scare teams in the playoffs, but this move would make sense for a team like the Cubs, who have been losing starting pitchers to the IL all season. 

Michael Wacha

The Royals and Tigers were supposed to be right up there with the Guardians in the fight for the AL Central. Baseball is a weird sport, so naturally the White Sox are in second place behind the Guardians, while the Royals and Tigers are hanging out in the cellar. The 34-year-old is having another productive season with a 4.19 xERA and 1.2 fWAR. This is another arm that isn’t going to propel the Cubs to the playoffs, but he should provide quality innings at the back of the rotation. If they add a Joe Ryan, Freddy Peralta, or even a Tarik Skubal, Wacha would be a great secondary move.

Pete Fairbanks

The Cubs might be wary of taking on another struggling arm, especially with the performance of Phil Maton, who was supposed to be one of their dependable, late-inning options. Fairbanks has a 7.41 ERA, but a 3.59 xERA. He has the highest BB/9 of his career so far, and has the second-highest homer rate trailing only his rookie season. He is on a one-year deal and it shouldn’t take much for the Marlins to move him. This addition would not solve the bullpen crisis, but it would give them another major-league arm to play with. 

A Mets Reliever or Two

If the Mets sell, they could accumulate a real asset or two for some of their relievers. Lefties David Peterson, Brooks Raley, and A.J. Minter should all be available. Righties Huascar Brazoban and Luke Weaver could also find themselves on the trade block. To maximize value, David Stearns likely won’t bundle these pitchers together or package one with Peralta, but there is plenty of value here for the Mets to cash in on.

Gus Varland Tier: Gus Varland

The Cubs can bring Varland home to Chicago and give him a pretty easy red-line commute to Wrigley Field. After missing the entire 2025 season, Varland is quietly putting together a solid season in the Nationals' pen. His 25 appearances lead the team, and his 3.27 FIP show he is a bit better of a pitcher than his 5.14 xERA indicates. Though the Nationals are flirting with a .500 record, they will certainly be selling off some pieces. After joining the Nats as a waiver claim, he has given them enough value to become an under-the-radar trade chip. Plus, some less knowledgeable fans may think they acquired his brother.