CHICAGO — Before Justin Fields threw his coaches under the bus, Theo Epstein was the Chicago sports figure who embodied the “F it” mentality. The current Bears quarterback and the former Cubs president of baseball operations seemingly have little in common, but that gunslinger persona is essential when a big-market, charter franchise feels a sense of inertia.

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The Cubs are approaching another one of those transformative moments. David Ross already received votes of confidence from the owner, the team president and his best players, but the manager will enter his fifth season on the hot seat. Rather than maintaining the farm system and letting the prospects grow, there will be a heightened sense of urgency to cash in those trade chips for right-now talent. Signing Cody Bellinger to the biggest contract in franchise history would only be a first step toward getting back onto the wild-card bubble. Missing the playoffs by one game, while carrying a payroll projected to settle just beneath Major League Baseball’s $230 million luxury-tax threshold is another angle to the September collapse.

Epstein once helped normalize the idea of tanking because he saw it as the most expedient way to build a championship team. Epstein pushed for a separate fund for baseball operations so that the Cubs could pursue Masahiro Tanaka and roll money over to sign Jon Lester. Epstein didn’t hesitate to trade prospects once the major-league roster was good enough, asking, “If not now, when?” Epstein fired two handpicked managers before hiring Joe Maddon, and then refused to even discuss the possibility of a contract extension for Maddon after the Cubs won 95 games in 2018, demanding more and promising a reckoning.

Jed Hoyer, of course, was there for all of it as Epstein’s longtime lieutenant with the Cubs and Boston Red Sox, a successful partnership that saw three World Series titles and the end of championship droughts that lasted 194 years combined. In handing the reins over to Hoyer after the pandemic-shortened 2020 season, Epstein acknowledged that he was great at “building and transformation and triumphing” and maybe “not as good and not as motivated by maintenance.”

Tom Ricketts, the chairman of his family’s ownership group, doesn’t want a super-team show as much as he believes the key to success is having a steady flow of young talent and a stable group of major-league players supplemented by the right free agents. Crane Kenney, the president of business operations, just completed his 30th season in the Cubs organization. There will be more continuity, but running it back with an 83-win team won’t be good enough.

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“Tom and Crane were really aggressive with the payroll this year,” Hoyer said during Tuesday’s end-of-season news conference at Wrigley Field. “We pushed the envelope this year. We were aggressive to build this team because they believed we could compete and we did. That momentum is certainly something that we want to capture and continue.”

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The Cubs’ $179 million Opening Day payroll ranked 14th out of 30 major-league clubs, according to the Associated Press, though that roster calculation did not include the final year of Jason Heyward’s $184 million contract and other expenses that count against the competitive balance tax. Hoyer’s multi-phase rebuild is designed to stagger the investments, even after committing more than $300 million to a class of free agents that included All-Star shortstop Dansby Swanson.

Maybe this isn’t the time to be quite so methodical and rational. Wrigley Field attendance improved but did not reach the 3 million mark, even with a surprising team that played so many entertaining games and remained in the playoff hunt until the penultimate day of the season. Marquee Sports Network’s ratings increased 34 percent for Cubs broadcasts this year, according to Sports Business Journal, though the NFL is king and the Bears still take up much of the oxygen on the city’s sports radio stations. Players like Swanson swear the team has begun creating a winning culture and setting high clubhouse standards. The organization has young talent and payroll flexibility, or what Epstein liked to describe as the game’s two most valuable currencies.

Cubs president of baseball operations Jed Hoyer intends to bring back pitcher Kyle Hendricks, whose contract includes a $16.5 million club option for next season: “We want to keep him as a Cub for next year and beyond.”

— Patrick Mooney (@PJ_Mooney) October 3, 2023

“Theo was referring to organizational health,” Hoyer said. “When you get to a place where you don’t have prospects and you don’t have available dollars, you’re stuck. We’re in a place now where our books are clean long term. Certainly, we do have young players. The organizational health is really strong. We’ll sit down, like every team will, over the next few weeks and talk through where we are financially. We haven’t done that yet.”

Nothing is guaranteed. The New York Mets and San Diego Padres will go down as two of the worst teams that money could buy. The playoffs won’t feature the Red Sox or New York Yankees, either. The Milwaukee Brewers, Miami Marlins and Arizona Diamondbacks finished ahead of the Cubs without being economic superpowers. But in a sport where everyone is hunting for the smallest edge — and Cubs fans on social media are overanalyzing every little decision Ross made — this is the obvious advantage.

The Cubs paid the luxury tax after their 2016 World Series campaign and again in 2019, when they missed the playoffs while carrying the National League’s highest payroll. There are other considerations that go into this calculus, like draft picks and bonus money for international signings. But after getting a small taste of winning again — and feeling that sting of loss at the end of the season — this is the time to say “F it.”

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“I don’t weigh it alone,” Hoyer said. “That will be a lot of conversations with Tom and the family, and with Crane and the business side. There’s been a willingness to go over in the past. We were over a number of times as the previous core got more expensive. And as we needed to supplement the roster, we did go over. Philosophically, we’ve shown a willingness to do it. It’s a budgetary question, but we also want to make sure that strategically you do it at the right time. We’ll have those discussions, but there’s no organizational mandate against it.”

(Photo of Jed Hoyer: Michael Reaves / Getty Images)