It's hard to overstate the stakes for the Chicago Cubs as they enter a winner-take-all Game 5 of the NLDS against the Milwaukee Brewers on Saturday night. There's the usual pressure that October baseball brings, of course, but that's just the start of it. There's also the years this Cubs team has spent patiently rebuilding to get to this point. And the patience Jed Hoyer has tested along the way. And the specter of Kyle Tucker's impending free agency, after trading a haul for him last winter. And the symbolic significance of a postseason series against the Brewers, not just your divisional nemesis but the team whose manager you poached two years ago.
It's a lot, is what we're saying. And yet, heading into the biggest game this franchise has seen in years, Craig Counsell will be handing the ball to ... lefty reliever Drew Pomeranz. Wait, what?
Drew Pomeranz’s Cinderella comeback story continues:
— Bob Nightengale (@BNightengale) October 11, 2025
The 36-year-old left-handed reliever, who had not pitched in the big leagues since 2021 before this year, will be the Chicago Cubs’ starter tonight in Game 5 against the Milwaukee Brewers.
Do not attempt to adjust your screen; the Cubs appear to be putting their season in the hands of a bullpen game. It's unclear exactly what Counsell's plan is beyond Pomeranz. It's possible that this is just an opener for Shota Imanaga, whose scheduled turn it is. But given that Pomeranz and Imanaga are both lefties, that seems unlikely; usually teams try to use their opener to get some sort of platoon advantage for the later innings.
More likely, Counsell has simply concluded that, without Cade Horton in the picture, he can't trust any of his available starters more than he trusts trying to cobble things together with relievers. And the most damning part is that he really might not be wrong.
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Cubs have only themselves to blame for sketchy playoff pitching situation
If you're a Cubs fan, this situation has to drive you up a wall. It would be one thing if Chicago were forced into this situation through circumstances beyond their control. And in some sense, I suppose that's true: Losing Justin Steele to Tommy John surgery was a huge blow, as was Imanaga's implosion down the stretch this season.
But Steele got hurt months ago, and Imanaga had warning signs under the hood that suggested regression (particularly home run regression) was coming. And yet, despite all of that, Hoyer chose to sit on his hands. He sat on his hands this winter, refusing to meaningfully address the starting rotation beyond the (admittedly shrewd) addition of Matthew Boyd. And he sat on his hands at the trade deadline, acquiring only righty Michael Soroka — who got torched when given the opportunity in Game 1 of this series.
This is hardly a case of hindsight being 20/20. From the moment last season ended, Cubs fans were begging their team to bolster their pitching depth. Hoyer just decided not to — coming to the conclusion, as he always seems to, that the prices simply weren't good value for the players available. The thing about that, though, is that if you're committed to being the only rational member of an irrational market, you're committed to coming in third or third place over and over again. Eventually, you need to just decide to go for it and do what's required to land a player who will make your team better.
Hoyer has yet to learn that aspect of the job, one that his mentor, Theo Epstein, knew all too well. And now it could come back to haunt the Cubs at the worst possible time.