Before the Chicago Cubs faced off against the Miami Marlins this weekend, Pete Crow-Armstrong, Pedro Ramirez, Matt Shaw, and BJ Murray Jr. got the chance to catch up with one of their old Iowa Cubs teammates.
Owen Caissie was in the ballpark, even as he continued to battle through recent neck spasms, and was at least able to catch up with his friends and make a pinch-hit appearance against his former team Friday. The former top prospect for the North Siders has been enjoying a steady job in right field with Miami since being dealt in the Edward Cabrera trade. It hasn't been smooth sailing in his first full season, though.
Owen Caissie catching up with his former Cubs teammates. pic.twitter.com/sZL3S1lZiw
— Tyler Boronski (@TylerBoronski) September 4, 2026
Caissie had recorded 312 plate appearances entering Sunday's series finale and, in that time, he has a .220/.285/.412, good for just an 88 wRC+. The prodigious power he was known for has been present to a degree, with 13 long balls to his name so far. However, he's also been plagued by the exact problem everyone expected — strikeouts. He's punching out an untenable 37.2 percent of the time while only walking 7.7 percent of the time. Among all players with 300 or more plate appearances, his strikeout rate is by far the highest, sitting 2.5 percent above Oneil Cruz in second place. With -7 outs above average, his defense has been similarly unspectacular.
In the first year of the Cabrera trade, both players have been a combination of injured and bad for their respective teams, but there's still plenty of time to change the narrative. There is an important lesson for the Cubs to take from Caissie's struggles as the offseason nears, though. For every top prospect that comes out of the gate swinging or turns into a superstar á la PCA, there are many more that can take years to reach their potential or never reach it at all. For a competitive big-league team that doesn't have depth like the Dodgers, there's risk in penciling any prospect into the plans.
At one point, Caissie was considered part of the plan to replace Kyle Tucker's production when the star right fielder left in free agency. However, the Cubs clearly understood with the Cabrera trade that prospects are lottery tickets and that controllable big-league help for a team on the rise was more important than clinging to a risk. They eventually opened up their pocketbooks to add Alex Bregman, who, after a rough start to the year, has become that veteran star presence this team needed. That had a ripple effect on the roster, too, strengthening the bench with Matt Shaw in a utility role and taking pressure off Moises Ballesteros at DH.
The Cubs need to be careful when letting Ian Happ and Seiya Suzuki walk
When big-league talent was lost, the Cubs didn't just let it ride and focus their attention elsewhere. They structured the roster to remain very competitive and give prospects chances under lower pressure. This offseason, they'll be faced with a similar predicament, but doubled, with both Ian Happ and Seiya Suzuki hitting free agency. Pitching will be the focus given how many of their starters are in their walk years, but that doesn't mean they should ignore potentially losing two bats with career wRC+ marks of 116 and 128, respectively.
There may be the temptation to go lighter, move Shaw to right, and cobble together a stopgap until one of their top prospects arrives. Three of their top five farmhands by MLB Pipeline are outfielders, including their #1 prospect, Josiah Hartshorn, who has emerged as a potentially special talent this year with a .298/.406/.562 slash line at High-A at just 19 years old. He's one to watch after becoming the first teenage Cubs minor leaguer to eclipse 20 home runs since Corey Patterson in 1999 and recently crossing the also-impressive 100 RBI threshold. Even so, his path to the big leagues is still long, and there can't be the assumption that he'll hit when he arrives.
In fact, none of the Cubs' current top outfield prospects are even in Triple-A. Yes, they may one day make an impact in Chicago, particularly Hartshorn, but this team is not built to be hedging right now. They're built to win, and they can absolutely afford to both address the rotation and, say, bring back one of the engines of their offense in Suzuki, even if the cost is high. Those prospects can also be used to address their other needs in a trade.
Caissie's early struggles should be an example of what this team got right. Even if he pans out and becomes a star in Miami eventually, it was the right call then to prioritize more immediate impact, and it would be the right call this offseason too.
