The Chicago Cubs won the 2016 World Series in the midst of what was arguably the most successful stretch in franchise history. Three consecutive trips to the NLCS, three division titles and five playoff appearances from 2015-2020 have left Cubs fans starving for more. The team has not won a game in the postseason since 2017, and Jed Hoyer is a lame-duck president of baseball operations. The pressure is on to deliver in 2025, but it all comes down to how aggressive Hoyer and Co. will be at the trade deadline.
Following a 4-5 road trip capped by an ugly 7-2 loss to the Philadelphia Phillies on Wednesday, the Cubs head back home with a 4.5-game lead over the St. Louis Cardinals in the NL Central. With a 41-27 record, Chicago is only a few games behind the New York Mets for the No. 1 seed in the National League. The Cubs have star power with Kyle Tucker and an emerging Pete Crow-Armstrong, while Ian Happ, Seiya Suzuki and Michael Busch have helped lead the best offense in MLB. Yet, there are still pieces missing before the Cubs can consider themselves true World Series contenders.
Hoyer has publicly confirmed the fact that the Cubs are indeed trying to improve their pitching staff. As he told Joel Sherman and Jon Heyman on a recent episode of their podcast The Show: “I think we’ll be looking for pitching, for sure. I think our guys have done a really good job at stepping up … But yeah, I think we’ll be looking for pitching, both rotation and in the bullpen. And that’s not a secret."
He can say that again. Veteran pitcher Colin Rea has done a solid job filling in for Justin Steele, who is out for the season after undergoing elbow surgery. However, Rea has regressed during the past couple weeks and is much better suited for a role in the bullpen. Ben Brown is going through his ups and downs in his first full MLB season; after his last start against the Phillies the right-hander's ERA is once again nearing six. Meanwhile, the Cubs are taking a cautious approach with Shōta Imanaga's return from a hamstring injury, with the lefty not expected back until the final week of June.
The bullpen has been carried by veterans Brad Keller, Caleb Thielbar and Drew Pomeranz, while Chris Flexen has contributed 17.1 scoreless innings and Ryan Pressly has rebounded after his awful blowup in May against the San Francisco Giants. However, the Cubs don't have a true closer, as Daniel Palencia has been filling in after Porter Hodge was placed on the injured list last month. Hodge took over the ninth after Pressly was demoted from the role.
Just as Hoyer made a statement over the offseason by trading for Tucker, adding legitimacy to the lineup, he has to do it again this summer to add firepower to the pitching staff.
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Trade 1: Moises Ballesteros, Jordan Wicks, Jonathon Long to Braves for Chris Sale
Sale would give the Cubs a true frontline starter to lead the rotation into the postseason. At 36 years old, Sale is not showing any signs of slowing down after coming off his Cy Young Award-winning season with the Atlanta Braves in 2024.
Through 14 starts in 2025, Sale has a 2.79 ERA with 107 strikeouts in 80.2 innings. The lefty currently ranks fourth in MLB among all starting pitchers with a 31.7% K rate.
The burning question regarding Sale's availability on the trade market is Atlanta's willingness to deal him away in July. Although the Braves are nine games below .500 and near the basement of the NL East, they have a propensity to still go for it as long as they're within striking distance. The NL Wild Card picture is loaded, though, and it's not hard to imagine Atlanta looking to sell come the end of July. Sale isn't a traditional rental, with a 2026 club option that's worth $18 million, but if the Braves can get meaningful future value for him they might consider it.
Moises Ballesteros would headline the trade package from the Cubs. The 21-year-old catching prospect has been at Triple-A since the end of the 2024 season and he hasn't stopped hitting: In 51 games with the Iowa Cubs this year the lefty has posted a 131 wRC+, slashing .337/.389/.507 with seven home runs. He can give veteran Sean Murphy a breather behind the plate and remain in the lineup as the designated hitter, depending on how far along he comes defensively during the next few years.
With Marcell Ozuna likely leaving Atlanta, Ballesteros and Jonathon Long could both get looks at DH in 2025. Long has broken out himself this year at Triple-A, hitting nine home runs with a 146 wRC+ in 245 plate appearances. The right-handed hitter has primarily played first base in his Minor League career, but Long has started in left field as well as third base to add to his versatility.
Ballesteros is currently ranked No. 3 in the Cubs' farm system and No. 57 overall according to MLB Pipeline. Long, 23, checks in at No. 12.
The Braves could get three MLB-ready players with the addition of Jordan Wicks. The 25-year-old could be a cheap option for the Braves as Wicks is still in the pre-arb stage of his career. Wicks was the Cubs' first-round pick in 2021, and was a fringe top-100 prospect a couple years back prior to his first call up to the Majors in 2023. He's battled through injury this season, but he's shown flashes of being a solid back-end rotation option in the recent past.
Trade 2: Owen Caissie, James Triantos, Brandon Birdsell to Marlins for Sandy Alcantara
The Miami Marlins are certainly waiting for Sandy Alcantara to return to his pre-Tommy John form as the 2022 NL Cy Young winner has struggled since returning to the mound. But there are signs that Alcantara is turning the corner, as the right-hander has only allowed two earned runs in his last two starts, striking out 10 and overall pitching more like his old self.
Sure, it's going to take a lot more than looking good against the Colorado Rockies and Pittsburgh Pirates for teams to step up their price for Alcantara, but the Cubs may have an edge when it comes to trade talks with the Marlins.
Chicago had a deal in place this past offseason to acquire left-handed starting pitcher Jesus Luzardo from Miami. It ultimately fell through because the Cubs didn't like the medicals, and a week later the Marlins traded Luzardo to the Phillies. If the Cubs didn't back out, they would have sent outfield prospect Owen Caissie over to Miami.
While those trade rumors were swirling, Cubs insider Bruce Levine reported that infield prospect James Triantos was another potential player that could have been involved in the trade for Luzardo. So, there's definitely interest from the Marlins in adding those guys to their farm system.
Adding Caissie to the Marlins would immediately make him the top hitting prospect in Miami's system. The left-handed hitting outfielder is currently ranked No. 46 in MLB Pipeline's top-100 list and is Chicago's No. 2 prospect. Caissie is in his second year at Triple-A, where he's put up a slash line of .255/.360/.490 with nine home runs and a 118 wRC+ in 228 plate appearances.
Triantos has been bothered by a couple injuries in 2025, so he's been limited to 33 games at Triple-A. Last year, he combined to hit an even .300 between his time at Double-A and Triple-A. The 22-year-old entered the 2025 season ranked No. 67 in MLB Pipeline's top-100 list.
The Marlins may also be intrigued by 25-year-old starting pitcher Brandon Birdsell. The righty posted a 3.91 ERA in 135.1 innings in 2024. The fifth-round pick out of Texas Tech in 2022 ended last season with a 3.57 ERA over his final 20 starts, striking out 109 batters in 106 innings of work.
Birdsell has been recovering from a shoulder injury that popped up in spring training, so Miami's medical team would have to feel good about his progress if he's included in this potential deal. Birdsell is the No. 7-ranked prospect in the Cubs' system.
Alcantara is under team control beyond 2025, as he's set to earn $17.3 million in 2026 and also has a club option worth $21 million for the 2027 season. Some fans point to his struggles so far this year, but it's easy to forget that pitchers often take a while after coming back from Tommy John before regaining their prior form. The 29-year-old has nearly 1,000 MLB innings under his belt and has a career 3.57 ERA in 159 games. Alcantara's numbers will get better frmo here, and as they do his price will go up this summer.
Luckily for the Cubs, they have a loaded farm system that can cater to any team's needs.
Trade 3: Kevin Alcantara, Luke Little, Javier Assad to Orioles for Zach Eflin and Felix Bautista
If the Cubs choose to go all-in for bullpen help, then they could entice the Baltimore Orioles with a package of two young players in Kevin Alcantara and Luke Little while also adding a dependable MLB pitcher in Javier Assad.
It's a tough pill to swallow for the Orioles, but their 2025 season has been a disaster and they could look to get out from under Zach Eflin's salary if things don't get better soon. The right-handed starting pitcher is making $18 million this season, while the big prize in this deal for the Cubs would be closer Felix Bautista.
Although Eflin isn't the frontline-type starting pitcher Cubs fans want, he still represents a big upgrade to the rotation and brings along a solid track record. The 31-year-old is now down to a 4.08 ERA in nine starts this season with a 1.09 WHIP. Eflin has posted a sub-four ERA as a starter since the beginning of the 2019 season and pitched well for Baltimore last year, recording a 2.60 ERA in 55.1 innings after he was acquired in a trade from the Tampa Bay Rays.
The headliner here is Bautista, who is coming off Tommy John surgery but is still pitching like one of the best closers in MLB. The hard-throwing righty is still under team control through the 2027 season via arbitration after signing a two-year, $2 million deal that expires following this year. In parts of three MLB seasons, Bautista has a 2.06 ERA with a 38.6% K rate and is 60-for-69 in save opportunities. He has a 3.32 ERA with 12 saves so far this year.
The Orioles could either see Alcantara as a future piece on their team or potentially flip him later on for more pitching help. Alcantara is currently ranked No. 4 in the Cubs' system and No. 70 overall according to MLB Pipeline.
As for Little, the 6-foot-8 lefty reliever has the makings of a future closer himself. In 38 big-league games with the Cubs he's recorded a 2.97 ERA with 40 strikeouts in 33.1 innings. Little is currently in Triple-A, where he's dominating to the tune of a 1.54 ERA in 23.1 innings.
The Cubs would obviously get the advantage overall in 2025 with the added value of a solid rotation arm to go with an elite closer, but the Orioles could ultimately get more value from Alcantara and Little, who will be cost-controlled for five or six more years. Plus, Assad could step into the Orioles rotation once he returns from an oblique injury, and he'll also come with three more years of pre-arb control.
Since making his MLB debut in 2022, Assad has recorded a 3.40 ERA in 70 total appearances, including 40 starts.