Kyle Tucker is headed toward a massive contract and Chicago Cubs fans are desperately hoping that the star outfielder continues his playing days at Wrigley Field. Although the front office hasn't engaged in active negotiations with Tucker's representatives on a long-term extension, Jed Hoyer has to be pleased with the team's success so far in 2025, hoping it'll lure the outfielder to remain in Chicago.
Tucker has been an excellent addition to the lineup, propping up the Cubs to the top of the NL Central. However, if the Cubs want Tucker to stick around, then they have to show him that they're willing to do everything possible to win now and sustain their success in the future.
Tucker is trying to lead the Cubs to their first postseason appearance since 2020, and first win in the playoffs since 2017. He's used to making deep runs in October, reaching at least the ALCS from 2019-23, with the Houston Astros. If the Cubs want any chance of retaining Tucker beyond 2025, they'll obviously have to blow him away with a huge deal, but they can also gain an edge by having him experience playoff baseball at Wrigley Field and proving to him that they'll build a true World Series contender.
These three dream trades could not only make the Cubs a dangerous team come October, they could go a long way towards keeping Tucker for the rest of his career.
Add ace potential to starting rotation
Shota Imanaga was a sight for sore eyes as he returned to a struggling starting rotation. The Cubs recently optioned Ben Brown to Triple-A and still have Colin Rea in the fifth slot. Matthew Boyd has been excellent throughout the year, but the other veteran in the rotation in Jameson Taillon has regressed and is starting to get crushed as the weather warms up.
Rookie Cade Horton has been solid since he was called up in May, but as the team has witnessed during June, the starting rotation needs an upgrade to prevent a decline down the stretch. More importantly, if the Cubs plan to make a title run, then they need another top of rotation type arm to pair up with Imanaga in the playoffs.
Miami Marlins starting pitcher Sandy Alcantara should still be the Cubs' No. 1 target at the trade deadline. He not only presents the Cubs the chance to acquire an ace-potential starter for this year, but beyond 2025, too. Alcantara is under team control through 2027, which shouldn't be overlooked by the Cubs because they'll have a few pending free agents in the rotation after next season.
If Alcantara continues to his recent stretch of good pitching, then the Cubs should not hesitate in their pursuit of the 2022 NL Cy Young winner. Imanaga and Alcantara would be a formidable 1-2 punch against any opponent in the postseason.
Create a lockdown bullpen
The Cubs are getting some unbelievable performances from unlikely relievers so far in 2025. Drew Pomeranz still hasn't allowed a run in 21.2 innings, while Brad Keller, Caleb Thielbar, and Daniel Palencia have been top-15 relievers in the National League.
Still, injuries can pop up at any moment, especially on the pitching staff, so it's imperative for the Cubs to add at least one more shut down reliever to the bullpen. Earlier this week USA Today's Bob Nightengale reported that the Cubs are interested in a pair of Pittsburgh Pirates pitchers, including closer David Bednar.
Despite having a poor 2024 season that saw the Pirates remove Bednar from the closer role, the right-hander is back to his dominant form. Following a stint at Triple-A back in April, Bednar has recorded a 2.03 ERA with a 36.8 K% in 26.2 innings. He's converted all 11 save opportunities this year and his addition to the Cubs' bullpen would make Craig Counsell feel invincible in the playoffs.
The cherry on top of a potential Bednar trade? The right-hander is still under team control for another year via arbitration.
Improve weak link with bold trade
While the Cubs have maintained a top-three offense through the first half of the season they still have one giant hole in their lineup. Rookie Matt Shaw has been a wonderful defender at third base, but the 23-year-old hasn't been able to sustain any consistency at the plate.
It would be a bold move, but trading for Eugenio Suarez and having him replace Shaw at third base would take this Cubs' lineup to another stratosphere. So far in 2025, Cubs' third basemen have combined to hit .198/.269/.261, resulting in a league-worst 55 wRC+. Shaw currently has a .596 OPS and has been trending the wrong way the entire month of June, posting a .478 OPS in his last 80 plate appearances.
Suarez is a free agent after 2025, but getting him is the ultimate all-in move for the Cubs this season. Is he truly necessary for this roster? Not exactly, but his power bat would provide more than enough backup for any of the other top hitters who go through slumps. Suarez already has 25 home runs in 78 games with the Arizona Diamondbacks, and he'd be a nightmare for opposing pitchers batting behind Tucker and Seiya Suzuki in the heart of the lineup.
Trading for Suarez would also improve the bench for the Cubs. Shaw could slide into a utility role, ousting either Jon Berti or Vidal Brujan, who have provided virtually nothing for the team this year.
The Cubs have to be bold at the trade deadline because the decisions they make this summer may ultimately have an effect on whether or not they'll be able to convince Tucker to stay with the organization. Winning could certainly entice the outfielder on top of a big paycheck.