This trade deadline is the moment that Cubs president Jed Hoyer has been waiting for

ST. LOUIS — Chicago Cubs president of baseball operations Jed Hoyer is invested in this group in a way that does not always come across when he talks about model projections, playoff probabilities and payroll flexibility. Systems and processes help keep him tethered, reducing some of the mood swings and randomness, but his personal stake in this venture is enormous.

The Cubs announced the hiring of Hoyer as Theo Epstein’s general manager in November 2011, back when Pete Crow-Armstrong was 9 years old, the St. Louis Cardinals had just won the World Series and Tarik Skubal was a teenager who would struggle to get noticed by Division I programs.

This means Hoyer served as the club’s No. 1 baseball executive or its second-in-command when each one of the 53 players the Cubs have used this season joined the organization, from first-round picks Ian Happ and Nico Hoerner to the 13 different relievers who have notched a save amid the constant roster churn.

With Monday’s trade deadline rapidly approaching, the next moves represent another defining moment. With Hoyer running the show, the Cubs have been built back up to the point where the idea of acquiring Skubal cannot be ruled out, even though the Detroit Tigers ace will become a free agent after this season.

This team is that good.

“Our group has some pretty special things about it,” Hoerner said. “We’re not perfect. We’re in a place now where we can definitely make some improvements to a team that’s already really strong.”

Hoyer’s “no reason to go halfway” sell-off in 2021, which shipped out iconic players from the team that ended a 108-year championship drought, yielded Crow-Armstrong, who has since developed into a superstar, delivering a unique MVP-level performance that cannot be taken for granted.

Valuing defense and stability, Hoyer courted free agents Dansby Swanson and Alex Bregman as he assembled a solid nucleus of everyday players. Hoyer made it a priority to reestablish the franchise’s presence in Japan, arranging deals for Seiya Suzuki and Shota Imanaga in an important international market.

The cold-blooded decision to sign Craig Counsell to a five-year, $40 million contract and then fire manager David Ross has worked out in Hoyer’s favor.

Pete Crow-Armstrong has developed into a superstar for the Cubs. (Scott Kane / Associated Press)

Although the Cubs should not be viewed as the prohibitive favorite for Skubal — the Los Angeles Dodgers, Milwaukee Brewers and Tampa Bay Rays have more robust farm systems — the interest in a two-time Cy Young Award winner as a rental pitcher signals an ambitious, open-minded pursuit.

The hunger to win a championship as the top-ranking baseball executive is “always there,” Hoyer said during the July reunion weekend for the 2016 World Series team at Wrigley Field.

“The times I’ve been fortunate enough to win, you take those moments and sort of put them up on a shelf in your mind and you move on,” he said. “I don’t wear my rings. The job is the next one.”

As someone who rode down Lake Shore Drive and Michigan Avenue in the championship parade, and celebrated two World Series titles during his tenure with the Boston Red Sox, Hoyer knows what a real contender looks like. That eye test will influence how aggressive the Cubs will be at the deadline. At minimum, the club will need an established starting pitcher and a proven high-leverage reliever.

“I try to not get overly emotional about it,” Hoyer said. “I try to stick to the numbers, and try to make sure that we’re doing things that make sense on paper. But, yeah, listen, I think our position-playing group is really, really good. We had a lull there for a while, but the offense and defense part of it is impressive. That’s a group that can win a lot of games in October.

“Obviously, the challenge for us has simply been pitching and pitching injuries. The whole team matters.”

Hoyer’s rational approach sometimes obscures how he’s been involved in some of the wildest rivalries, most consequential deals and biggest moments in baseball history.

Spending Thanksgiving at Curt Schilling’s Arizona home with Epstein — and then failing to execute a blockbuster trade for Alex Rodriguez — propelled the Red Sox toward finally beating the New York Yankees and winning the 2004 World Series that ended an 86-year drought.

The 2016 Cubs felt the century-and-counting weight when Epstein acquired rental closer Aroldis Chapman from the Yankees for uber-prospect Gleyber Torres and memorably asked, “If not now, when?”

“You use the experience,” Counsell said. “It gives you more perspective, and a more well-rounded perspective of how these things go down. It’s situationally, buyers and sellers, what rentals get, how people are motivated, relationships with decision-makers, and understanding them. Mistakes, successes, I think that sharpens your instincts. That’s the value of experience.”

“Our group has some pretty special things about it,” Nico Hoerner said. “We’re not perfect. We’re in a place now where we can definitely make some improvements to a team that’s already really strong.” (Nam Y. Huh / Associated Press)

When the defending champs needed a midseason boost in 2017, conventional wisdom held that Chicago White Sox owner Jerry Reinsdorf would not let his front office deal with a crosstown rival, but the Cubs acquired Jose Quintana in a trade that shocked the city’s baseball fans and sports media.

Even within the restricted environment of the pandemic-shortened 2020 season, the Cubs traded for multiple major-league players to deepen a team that would win a division title.

As Hoyer felt the mounting pressure as a lame-duck executive going into 2025, he went against the projection models and traded for Kyle Tucker, getting an All-Star in his walk year while giving up 14 potential seasons of club control over Cam Smith, Isaac Paredes and Hayden Wesneski, knowing the Houston Astros would ultimately win that deal on paper over time.

Days before last year’s trade deadline, the Cubs announced Hoyer had signed a contract extension without specifying the length of the deal. Hoyer’s front office then made a series of safe, sensible deals that incrementally improved the roster without substantially raising the club’s ceiling.

Once again, Hoyer is on the clock, but this time the players feel a different sense of momentum. As rap music blasted inside the visitors’ clubhouse at Busch Stadium after Thursday afternoon’s 4-2 win over the Cardinals in 10 innings, Bregman observed, “This series was probably the most consistent baseball we’ve played in all facets of the game.”

The Cubs won three of four games on the road against their historic rival, the only loss being Wednesday night’s 3-2 walk-off defeat in the 10th inning. Milwaukee’s lead in the National League Central is down to 5 ½ games, and Wrigley Field will be rocking for this weekend’s marquee series against the Yankees.

By the time Imanaga throws Friday’s first pitch, scheduled for 1:20 p.m. CT, there will be less than 76 hours until the trade deadline. Hoyer might not be the most desperate buyer or an impulsive dealmaker, but he has significant trade chips on the major-league roster and in the upper levels of Chicago’s farm system, a team worthy of reinvestment and enough experience to know that these opportunities don’t come around that often.

“It’s all risk,” Counsell said. “Players don’t like talk about the future. Fans don’t like talk about the future. But he has a responsibility for the future. It’s one of the hardest parts about that job.”