The Chicago Cubs are understandably chasing the October glory. While doing so, they have toed a fine line between strategic ambitions and unintended collateral damage. Let’s just believe for a second that the Cubs will invest $500 million to extend their star Kyle Tucker. Although it’s very unlikely that they will spend that handsome money on him. But even if they do, it won’t stop Tucker and his agent from testing the market for a higher bid. The odds are stacked more towards Tucker finding a new home. If that happens, the Cubs’ attention would naturally lean on his successor.

It’s their top prospect, Owen Caissie. He’s highly regarded around the league and is comfortable sitting amongst the top 100 prospects of the league. Cassie has been looking all set to display his flashes of brilliance at the major league level.

Throughout this season, he has recorded a slash line of .282/.380/.588 with 20 home runs, 26 doubles, two triples and 47 RBIs. While he looks every bit of Tucker 2.0, the Cubs have done something that has given him a reason to be upset.

At this trade deadline, the Cubs were inclined towards adding controllable starting pitching. Phenoms like Mitch Keller from the Pirates and Edwin Cabrera from the Marlins were reportedly their targets. Apparently, the word out there was that Owen Caissie would be a part of the Keller or Cabrera deal.

Yes, the Cubs were rumored to part ways with their top prospect. However, the deal never materialized, and the Cubs never pulled the trigger. But just so you know, Caissie’s name has floated around in the trade buzz not since this July but since the off-season. And naturally so, Caissie felt every bit of it.

During an interview with the Des Moines Register, he admitted, “I was pretty nervous. I didn’t really have any feelings towards it—whether I was going or not. But I know a lot of people are surprised. But, I guess, I’m not really…if I would have been traded, OK. If I didn’t, great, I’m still with the Cubs.”

Sure, his remarks don’t imply that he’s holding a grudge with the Cubs. However, it did get to him. The Cubs will hold onto Caissie probably because they are unsure about Tucker’s future. In case they lose the grip on him, they are holding onto Caissie in the name of strong backup. He’s playing exceptionally at Iowa and ideally, the Cubs wouldn’t have dangled his name in the trade discussions for over 6 months.

Despite the bone to pick, Caissie is relieved to be with the Cubs

At the 2025 trade deadline, the Cubs added pitchers Taylor Rogers, Michael Soroka, and Andrew Kittredge and the infielder/outfielder Willi Castro. These moves were pretty impressive; however, the most surprising move was the one the Cubs didn’t make. They did not add a frontline elite starter to handle the rotation.

The Cubs have an attractive farm system and their Iowa team includes 10 of the organization’s Top 30 prospects. It led many to believe that the Cubs would crack a deal for a starter; however, they didn’t. Meanwhile, Caissie, along with other prospects—Kevin Alcantara, James Triantos, and Jonathon Long expected to be on the move.

But when the deadline passed and they stayed, it brought them a sense of relief. “You were seeing everywhere like me, Johnny, and Kevin would be traded.’ It was funny. We were all hitting and we’re like, ‘We’re still Iowa Cubs.’ It was a relieving moment.” Caissie admitted.

Keeping Caissie shows that the Cubs aren’t sure about Kyle Tucker’s future, so they’re holding on to a strong backup in case they lose a player as talented as him. Ideally, they wouldn’t have dangled Caissie in trade talks for over six months—especially since he’s their top prospect and playing really well in Iowa. He ought to be treated like the future MLB star he is.

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