Over the past year, Jed Hoyer made three moves aimed toward avoiding the outcome the Cubs faced against the Milwaukee Brewers last October in the NLDS. They traded for Edward Cabrera, Kevin Gausman, and Clay Holmes to avoid running out of effective options during the playoffs. Cabrera was left off the Cubs' Wild Card roster this year, Gausman pitched less than four innings and was ineffective, and Holmes never factored into the pitching equation.
Once the Cubs revealed that Gausman would be the starter for Game 2, they set themselves up to be in a position where Holmes was ultimately not used in the series. Sure enough, outside of briefly warming up near the end of Wednesday's game, the situation never called for Holmes to be used.
It's the difficult part about discussing trades in hindsight. Trading for Holmes was a no-brainer at the deadline. The team had a need for pitching across the first several months of the season, and had it not been addressed, the Cubs may not have even reached the playoffs. But, Holmes being a free agent, the Cubs giving up a top prospect in Jefferson Rojas, it does put Hoyer and the front office to re-evaluate the process when it comes to their pitching additions.
Cubs gave up their #1 prospect Owen Caissie for Edward Cabrera this past off-season who didn’t even make the Wild Card roster.
— Cubs Zone (@CubsZone) October 1, 2026
Cubs gave up their #2 prospect Jefferson Rojas for Clay Holmes at the trade deadline who still has not made an appearance this postseason. pic.twitter.com/optiWDVYrs
Cubs' Wild Card exit exposed painful reality of Jed Hoyer's biggest pitching gambles
The Cubs paid steep prices in their trades for starting pitchers over the past year, and they have very little to show for it.
Now, in the case of Holmes, it's almost a matter of circumstance. He last pitched for the Cubs last Friday, when there was still chance for the team to secure the top Wild Card spot. Given that reality, it would have been foolish for Craig Counsell not to use Holmes against the Red Sox. That said, if the debate for Game 2 on Wednesday was starting Gausman, who was less than 100%, or Holmes on short rest, perhaps Counsell should have went with the latter.
Of course, there's also the matter of the struggles Holmes had during the final month of the regular season, and it could be tied directly to the Cubs' pitching infrastructure. That bleeds into the problem the Cubs are facing with Edward Cabrera this offseason and figuring out why he struggled to the extent he did last season.
Something is amiss with the decision-making in the Cubs' front office. The big gambles that Hoyer has made for upgrades hasn't paid off. Until that changes, the stuck-in-the-mud feeling that the Cubs have had over the last two seasons will continue to be present.
