Owen Caissie's imminent arrival is a crossroad moment for Chicago Cubs

Chicago Cubs President of Baseball Operations Jed Hoyer has put the stock in the team's farm system since replacing Theo Epstein after the pandemic-shortened 2020 season.

While Epstein's planned exit was after the 2021 season, the pandemic accelerated the need for the Cubs to teardown a core that won the 2016 World Series.

The trade that kickstarted the teardown for the Cubs was moving Yu Darvish to the San Diego Padres for a package of lottery tickets with outfield prospect Owen Caissie being one of the final pieces to be included in the deal.

As it turns out, Caissie has proven to be the prized prospect from that trade. Caissie's power has put him near the top of the Cubs' prospect rankings and beginning in September, he could be an important piece to the Cubs' 2025 roster.

Caissie isn't on the Cubs' 40-man roster but will need to be prior to December; otherwise, the Cubs will risk losing him in the Rule 5 draft. Needless to say, Caissie being placed on the 40-man roster is a mere formality at this point. Given that fact, as Sahadev Sharma and Patrick Mooney point out in The Athletic (Subscription Required), Caissie is likely to get a look at the Major League level in September.

Caissie's arrival at the Major League level will mark the endgame for Hoyer's strategy.

Jed Hoyer's fate will be tied to the success of the team's farm system at the Major League level.

Hoyer is entering the final year of his contract with the Cubs in 2025 and while there isn't a scenario where he would be fired by the organization, failure to make the postseason in his five-year run would be such an egregious offense that even Tom Ricketts wouldn't defend bringing him back.

Hoyer has chosen, due to free-agent spending and trade choices, to live and die with the success of his farm system.

That is not meant to put all the pressure on Caissie's shoulders but is to emphasize that now is the time for Hoyer's plan to be successful. It's a risky proposition, pinning your job security on prospects who haven't played at the Major League level to be the reason why your team returns to contention, but it is the path Hoyer has chosen.