Chicago Cubs prospect deemed most likely to be dealt at trade deadline

After arriving in the Yu Darvish trade, Caissie has gone on to appear in 472 minor league games for the Cubs. He is hitting a robust .275 with 71 home runs, 279 RBI and 33 stolen bases. The outfielder has turned the corner offensively over his past two seasons hitting 22 home runs and driving in 84 RBI in 2023. He followed that up with 19 home runs, 75 RBI and 11 stolen bases during the 2024 campaign.

Caissie returned to Triple-A to begin the 2025 campaign, appearing in 66 games thus far. He is hitting .258 with 12 home runs, 33 RBI and three stolen bases. The outfielder ranks as the top prospect in Chicago’s organization and the 43-best in all of baseball, via MLB Pipeline.

The only problem for Cassie is that he is blocked at the major league level. The Cubs have a pair of All-Star outfielders in Kyle Tucker and Pete Crow-Armstrong. Ian Happ is holding down the fort in left. As it stands, there’s simply no place for Cassie.

Tucker could leave as a free agent after the season, opening up a spot. But the Cubs will likely try to sign him to a long-term deal. In that case, Caissie’s best value to Chicago could come as a trade chip.

What Chicago Cubs are looking for 

For as good as their offense is, the Cubs have struggled to get consistent production from third base. They could look to supercharge their lineup with another slugger at the hot corner. Still, it seems more likely that at least when it comes to Caissie, Chicago would be chasing the best pitching targets available.

Sandy Alcantara of the Miami Marlins has been heavily connected to the team. He has struggled mightily in 2025, but he is a former Cy Young winner and under team control through 2027. He would be arguably the biggest haul Chicago could fetch barring an unknown name being available.

The Arizona Diamondbacks have a pair of intriguing pitchers in Zac Gallen and Merrill Kelly. The 2025 season hasn’t gotten Gallen’s way, but he is a former All-Star and came into the campaign off of three straight years with a sub-3.70 ERA. Kelly has put up a 3.55 ERA and a 103/29 K/BB ratio. Either option would be a strong fit in Chicago’s offense.

The list goes on from there, including players such as Seth Lugo of the Kansas City Royals, Luis Severino of the Athletics or Tyler Mahle of the Texas Rangers. Name a player on the trade block, the Cubs will be involved.

But they aren’t just going to give Caissie away. Despite their outfield roadblock, they now how much potential the prospect has. Still, if he helps land Chicago a top flight starter, Caissie’s time on the North Side will be ending soon.