Day 2 of the 2026 Cubs Convention had all the usual beats-Jed Hoyer and Carter Hawkins opening the day, Craig Counsell following shortly after, and Boog Sciambi guiding the conversations from the moderator’s chair. But if you’ve been paying attention to this team over the past few years, you probably noticed something different this time around: the mood.
And not just among fans. The Cubs’ leadership group brought a noticeably lighter, more confident energy to the stage-an energy that only comes after a season where things finally start to click.
Jed Hoyer, the Cubs’ President of Baseball Operations, set the tone early. Dressed in a Bears jersey, he looked more like a guy ready to tailgate than someone fielding questions about long-term payroll strategy.
But make no mistake-his answers were as clear and calculated as ever. What stood out, though, was the ease with which he delivered them.
Whether he was breaking down the team’s approach to deferred contracts or telling stories from his days as a teenage bat boy for the Reds, Hoyer seemed unburdened. Winning will do that.
The biggest headline from the front office session revolved around those deferred contracts. The recent signing of Alex Bregman marked the first time this Cubs regime has gone that route in free agency, and Hoyer made it clear: it won’t be the last.
That’s a significant shift in approach, and it opens up a new lane for the Cubs to stay aggressive in a market where financial flexibility can make or break a deal. If they’re willing to play that game, it could mean more talent coming through Wrigley’s doors-without blowing up the long-term books.
General Manager Carter Hawkins echoed that sentiment while also showing a bit of levity. When asked about a comment he made during the 2032 trade deadline-one that stirred up plenty of fan chatter-he joked that Hoyer told him the next day, “You probably shouldn’t have said that.”
Hawkins laughed it off, saying he did it to take some pressure off Jed. It was a small moment, but one that showed how aligned and at ease this front office really is right now.
Then came Craig Counsell, who’s always had a knack for connecting with fans in these settings. He spoke candidly about roster construction and bullpen usage, but one of the more intriguing takeaways was his vision for Matt Shaw.
Counsell didn’t mince words-Shaw’s going to see time in the outfield. The comparison to Kris Bryant’s 2016 role wasn’t accidental.
Counsell sees Shaw as a versatile piece who can move around the diamond and still get regular at-bats, even with an infield that rarely takes a day off. That’s a big vote of confidence for a young player looking to carve out a meaningful role on a contending roster.
And then there were the stories-the kind that don’t show up in box scores but give fans a peek behind the curtain. Counsell recalled a moment from last season when Ryan Flaherty got tossed from a game against the Red Sox.
Turns out, it was actually John Mallee who made the offending comment. Counsell had to negotiate with the umpires about which coach would leave the dugout, and the whole situation ended with his family turning a photo of him arguing into a coaster they now use for guests.
It’s classic Counsell-sharp, self-aware, and always good for a laugh.
What really stood out across all these panels wasn’t a blockbuster announcement or a bold prediction-it was the sense of calm. After a season that saw the Cubs push the Brewers to five games in the NLDS and land both a major trade and a marquee free agent, the people steering this ship seemed genuinely comfortable with where things stand. That’s a far cry from the more tense, defensive tone we’ve seen in years past, when fan questions often carried a sharper edge and the answers felt more guarded.
Of course, there’s always another challenge on the horizon. CBA negotiations loom, and the grind of a full season has a way of testing even the most relaxed teams.
But for now, the Cubs’ leadership group is enjoying the moment-and so are the fans. After all, these are the kind of weekends that remind you why you stick with a team through the ups and downs.
Because every once in a while, it all starts to come together.