With their pitchers and catchers already in camp, the 2025 spring training period has begun for the Chicago Cubs. Speculation has already begun whether Japanese ace Shota Imanaga will pitch during the Tokyo Series next month. Spoiler alert, he will, according to Cubs manager Craig Counsell. Entering their skipper’s second season at the helm, Chicago will look to make it back to the postseason this year.
President of baseball operations Jed Hoyer is now in the last year of his contract. He’s already made one massive trade this offseason, acquiring superstar outfielder Kyle Tucker from the Houston Astros. The package of players he sent back in return included top prospect Cam Smith, third baseman Isaac Paredes and pitcher Hayden Wesneski. With third base now open, the hope is that another rising minor leaguer, Matt Shaw, will take over the spot during camp.
There are still avenues in which Hoyer could improve the team. Their pitching staff could use more major-league ready talent and adding another bat that can contribute every day would be good as well. As presently constructed, the Cubbies could make the playoffs. However, they might not make it that far. If Hoyer wants a new deal, a long postseason run might be required. If that’s the case, then here’s one perfect seven-player trade that they can swing with the soon-to-be home residents of Sin City, the Athletics.
Cubs looking to make return to postseason in 2025

Hoyer’s current contract situation does make this season a critical one. Furthermore, ownership would like to see more progress on the field under Counsell, who is currently the highest-paid manager in the majors. The Tucker trade is proof that the Cubs want to take that next step. Yet, it’s apparent that more talent is needed. If they can add two or three contributors, ones that will contribute at least 1-3 WAR a piece, would be ideal.
Putting together a deal that includes that many players can be tough. However, getting on the phone with the A’s might do the Cubs some good. The reasons for this are multiple. First, even though the team wants to get back to the postseason, they are also looking to cut payroll. The Athletics need to add payroll to avoid potential grievances from the MLBPA. Second, both teams have depth that could help out the other. Lastly, the A’s are more willing to make moves before their move to Las Vegas in a couple years. Bringing in more established major league talent plus young pieces would be a good thing.
Related Chicago Cubs NewsArticle continues below
In this proposed deal, the Cubs would acquire outfielder JJ Bleday, starting pitcher JP Sears and closer Mason Miller for four players: outfielders Seiya Suzuki and Owen Caissie plus starting pitchers Jameson Taillon and Ben Brown. A possible fifth piece from Chicago to the Athletics could really push this deal over the edge, but in a perfect world, this is how it would look.
Upgrading talent across board makes Cubs even deeper
In Bleday, they’d have a ready-made outfielder that can play in all three positions. It would solidify the outfield rotation as well, as they would have the quarter of Tucker, Bleday, Ian Happ and Pete Crow-Armstrong. Not too bad at all. Adding Sears to a starting five to replace Taillon while cutting the former New York Yankee’s salary would be a boon for Hoyer and the Cubs’ brass.
Miller would be the crown jewel though, as he would make the bullpen even stronger. Recently, Chicago pulled another trade with Houston, this time for reliever Ryan Pressly. The former Astro is slated to be the closer for the Cubbies at the moment, but he’s also excelled in a setup role. So, in either scenario, Miller’s elite velocity and strikeout stuff would be very welcome at the backend of the Cubs’ bullpen.
Shedding Suzuki and Taillon would meet the mandate to reduce payroll and open up roster space. There are a few more talented players in the Chicago minor league system that will be in the majors sooner rather than later. That’s why trading young players like Brown and Caissie can work in this type of deal, but it also stings as well.
It’s moves like this that make champions. By upgrading talent in multiple places on the roster, the Cubs will be deeper and more dangerous. In a National League that features the reigning World Series champions (will the Los Angeles Dodgers please stand up?), not to mention multiple 90-plus win teams in 2024, more talent will be needed to succeed in October. If they don’t succeed in 2025, then quite a few jobs may change at Wrigley Field by this time next year.