It wasn’t supposed to look like this in June. The Cubs had mapped out a summer of dominance, anchored by their ace, Justin Steele, bulldozing through lineups, and their newly assembled offense torching opposing pitchers. But then Steele went down, and suddenly, the wind at Wrigley feels a little less certain. Steele’s injury didn’t just leave a hole in the rotation; it cracked open a much bigger issue: Jed Hoyer is out of excuses.

For a franchise with playoff odds sitting at 88.5%, mediocrity isn’t acceptable. And while the Cubs have made the leap from rebuilding to contending, their current roster still has a glaring hole. With Ben Brown’s 5.71 ERA and Colin Rea’s inconsistency, the rotation lacks the depth required to survive postseason fire. ESPN has taken notice, and this week, Buster Olney delivered a blunt assessment: Hoyer is now one of the MLB executives under the most pressure as the Cubs enter the season’s turning point.

“Chicago is so good, its offense so dynamic and versatile, its defense so efficient that one evaluator believes the question for Hoyer is not whether the Cubs will make the playoffs… but what will make them more dangerous in the meaningful games they’re bound to play at the end of the season?” Olney wrote in ESPN’s latest report.

And that’s the entire point. The Cubs aren’t a feel-good, overachieving squad anymore. They’re built to win, with star power in Kyle Tucker (a free agent after the season) and strong fundamentals across the board. But no matter how many runs they score, without another legitimate arm to pair with Shōta Imanaga, they risk folding in October.

That’s why Jed Hoyer’s next move will define the year. Whether it’s a trade for Zac Gallen, Merrill Kelly, or Zach Eflin, the Cubs need more than innings; they need a postseason-caliber starter who can stop a losing streak and start a Game 1. There’s no time for half-measures.

Chicago’s expectations have shifted. A playoff berth is no longer the goal; it’s the baseline. Anything short of a deep run will raise one big question in the offseason: Did Jed Hoyer do enough when it mattered most?

‘It’s there for Jed Hoyer’: Insider signals trade market is open

Hoyer may be sitting on one of the most enviable positions in baseball right now: a contending roster, financial flexibility, and a clear runway to make impact moves. After taking three of four from the Pirates, the Cubs not only hold a 5.5-game lead in the NL Central but also boast a 44–28 record, trailing only the Mets and Tigers across the league. But with the trade deadline looming, insiders believe the next step is clear: get aggressive and get an ace.

Veteran MLB insider Bruce Levine lit the spark on Monday, telling 670 The Score’s “Mully & Haugh Show” that the market is primed for Jed Hoyer to strike. “I’ve been talking to a lot of people over the last four or five days about possible trades,” Levine said. “And everybody says it’s there for Hoyer.” With the front office reportedly saving significant funds by not signing Cody Bellinger to a massive deal or landing Rafael Devers or Alex Bregman, the Cubs now have “$30 million times four” worth of unspent ammo, and that could turn into either a frontline starter or a run-producing bat.

And it might not be one or the other. Levine hinted that the Cubs’ deadline plans might be two-pronged, especially given their potent but still patchable lineup. “So, there’s money there for Hoyer to spend,” he added. “It’s up to him to decide how he wants to do that, and is it going to be an ace starting pitcher? … Do they need a little fortification with offense? It’s right there. Maybe they can do a little of both.”

With Chicago entering an off-day before a crucial home series against Milwaukee, the clock isn’t just ticking; it’s inviting Jed Hoyer to take full control of the NL Central arms race.