Revisiting the Aroldis Chapman Trade One Decade Later: Will the 2026 Cubs Pull Off Another Historic Deal?

[Joe Sbertoli]

Image courtesy of © David Richard-Imagn Images

The incredible postseason run the Chicago Cubs went on in 2016 that resulted in their first World Series championship in 108 years is quickly approaching its ten-year anniversary. There were so many moments and decisions that led to breaking the “Curse of the Billy Goat” that played a role in securing the title. Arguably the biggest in-season move the Cubs' front office made that year was going “all-in” at the trade deadline by giving up a four-player haul to the Yankees in order to acquire All-Star closer Aroldis Chapman. Chapman played lights out that season for both franchises, finishing the year with a 1.55 ERA and 90 strikeouts in 58 innings, to go along with 36 saves. His production during his time with the Cubs was remarkable. He posted a 1.01 ERA, 46 strikeouts in 26 2/3 innings, and 16 saves.

The Cubs traded for Chapman on July 25, 2016 and at the time, the team had the best record in baseball. They were 20 games above .500 with a 7.5-game lead over the second-place St. Louis Cardinals within the Central Division. The belief that 2016 could finally be the year skyrocketed within the organization and fanbase alike. The best team in baseball added one of the most dominant closers in baseball. I get fired up just reminiscing about that trade and it got me wondering: Could 2026 be the year the Cubs make a splash move at the trade deadline again in an attempt to put everything on the line to win another championship? If they do, what would a similar trade cost them? 

There has been a buzz and excitement around this year's Cubs team with the additions of Edward Cabrera (RHP) and Alex Bregman (3B) to a roster that returns most of the players that defeated the San Diego Padres in the playoffs last year before exiting in the National League Division Series. It is not unreasonable to think that the 2026 North Siders could find themselves positioned for a deep postseason run by the trade deadline again this year as they did in 2016. They will have to compete with the other top-tier teams in the National League, most notably the Los Angeles Dodgers who are coming off back-to-back championships, in order to even reach the World Series. A big move at the deadline could add to the depth and confidence of this year’s team.

The package of players that the Cubs sent to the Yankees for Chapman was considered a very steep price for a reliever that was in the final year of his contract. They gave up prospects Gleyber Torres (INF), who was the team's top prospect at the time, Billy McKinney (OF), listed as their sixth-best prospect, and Rashad Crawford (OF) along with bullpen arm Adam Warren (RHP). The Cubs were willing to ship out potential long-term contributors for a player that would be on the roster for only a few months. It was 100% the right decision in hindsight. Gleyber Torres was the only player from that group to have sustained high-level success over a long MLB career (career stats: .264 BA, 1006 H, 515 RBI, and 154 HR). He became a two-time All Star during his time with the Yankees and is still in the league today with the Detroit Tigers.

It is challenging to predict the exact positions that the Cubs may target at the trade deadline in 2026 if they are in the playoff mix, since injuries or lack of production from current players could factor into that decision. As it stands today, adding another dominant arm (similar to the Chapman trade in 2016) or bat-first slugger seem like the most likely areas they may focus on. If they attempt to acquire a fate-changing player such as Kris Bubic (LHP) of the Kansas City Royals, Pablo Lopez (RHP) of the Minnesota Twins, or Yandy Diaz (INF/DH) of the Tampa Bay Rays, it will require a willingness to part ways with young talent within the organization again. 

The Cubs have already dealt some of their talented minor-league players in order to acquire Edward Cabrera this offseason. They sent Owen Caissie (OF), Cristian Hernandez (INF) and Edgardo De Leon (INF) to the Miami Marlins, but there are still plenty of players that would certainly intrigue other teams looking to add multiple young players in exchange for a transformative veteran player. A trade of this magnitude would most likely require at least one of their top four prospects, which include Moises Ballesteros (C/DH), Jaxon Wiggins (RHP), Jefferson Rojas (INF), or Kevin Alcantara (OF), along with a couple other quality pieces with upside. Players such as James Triantos (INF) or Kaleb Wing (RHP) could be coveted as well.

Will Jed Hoyer decide this season is the right time to take another big swing? Only time will tell, but his aggressiveness this offseason seems to demonstrate a belief that this Cubs team is ready for a deep playoff run. The farm system no longer features a plethora of Top-100 prospects like it has in recent years, so they should feel some urgency to maximize the potential that this lineup is capable of now, rather than looking to the future. As antithetical as that may seem to this front office's M.O., remember that this is the final season before the expected 2027 lockout. Cost and revenue certainty is valuable for any organization, and in Major League Baseball, that ends in 2026.

It will be exciting to monitor all of the action this year in July as the trade deadline approaches if the Cubs can position themselves as buyers for another push in the postseason. Adding Aroldis Chapman was a massive shot in the arm to a loaded Cubs team in 2016. Here's to hoping we as fans get that same jolt in just a few short months.

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