How past trade deadline failures shaped Cubs approach in 2025

The Chicago Cubs were burned by their 2017 trade with the Chicago White Sox, and it seems to be Jed Hoyer's determination that it never happens again. The infamous trade saw the Cubs give up their top hitting prospect, Eloy Jimenez, and their top pitching prospect, Dylan Cease, to address a massive need in their starting rotation with the addition of Jose Quintana.

The deal was made a few weeks before the 2017 trade deadline, and it effectively saw the Cubs set the price for a controllable starting pitcher. Something Hoyer's front office wasn't willing to do this time around.

Now, the water carriers for Hoyer are out in full force the day after the deadline. A report from Cubs Insider indicates that among the trades the Cubs were looking to make ahead of the deadline, the price would have included Matt Shaw, Cade Horton, and a top prospect. It's certainly possible those were the names asked about as the Cubs looked for a controllable ace ahead of the deadline, but the report also reeks of Hoyer's front office doing damage control after once again becoming a punchline.

This Cubs trade strategy feels like a reaction to past deadline pain

We also have to acknowledge the other reports that the Cubs were reluctant to include Moises Ballesteros in any deal they were discussing. At the time, it felt like posturing, considering the deadline was a mere hours away. Now, with the Cubs flat out saying they weren't going to pay the price that the market dictated, it's confirmation that Hoyer didn't want to go through the burn of wasting top prospects as trade capital as he did in 2017.

The market is the market, and the Cubs need to face the reality that the trend is going in a direction where they must alter their strategy--or they will always be the bridesmaid, and never the bride. Even that is generous for Hoyer's front office, as they often aren't even invited to the wedding.

Past failures for the Cubs' front office are only setting the stage for continued failures for Hoyer and his front office. There's very little evidence to believe that will change any time soon.

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