Even before the Carlos Correa news broke late Tuesday night, the internal tensions between the business and baseball sides of the Chicago Cubs organization had spilled into the open. With astronomical contracts resetting the market for top free agents, Cubs president of baseball operations Crane Kenney deflected the external pressure to do something onto Jed Hoyer, the No. 1 baseball executive at Wrigley Field. Hoyer believes publicly discussing payroll parameters puts the Cubs at a competitive disadvantage. Kenney, however, recently appeared on the team’s flagship radio station and again revealed that Hoyer’s group still has leftover money from last season’s budget.

“The business is still healthy and that left Jed with a lot of money to spend this year,” Kenney told 670 The Score. “Like last year, where he didn’t spend all the money he had. Last year, he just didn’t see transactions that made sense to him. I hope there are transactions that make sense to us this year to spend all the money he has.”

You can cross Correa’s name off that wish list after the All-Star shortstop reached an agreement with the Giants on a 13-year, $350 million contract, making it two consecutive offseasons that the Cubs whiffed on the generational talent who once drew comparisons to Alex Rodriguez during a dazzling pre-draft workout at Wrigley Field.

Carlos Correa (Jeffrey Becker / USA Today)

Kenney ostensibly joined The Score’s morning show last week to talk about the National Baseball Hall of Fame and Museum honoring Cubs radio broadcaster Pat Hughes with the 2023 Ford C. Frick Award. But after a frenetic Winter Meetings that saw the Cubs make deals with former National League MVP Cody Bellinger and starting pitcher Jameson Taillon, the questions inevitably turned toward what’s next for Hoyer’s front office and what’s possible under the directives from chairman Tom Ricketts and his family’s ownership group.

Curiously, the Cubs structured Bellinger’s one-year, $17.5 million contract with a $12 million base salary in 2023 and a $5.5 million buyout of a mutual option for 2024. Those financial maneuverings came at a time when the Phillies stretched Trea Turner’s $300 million megadeal over 11 seasons to reduce the contract’s average annual value for luxury-tax purposes. The Padres followed a similar strategy with Xander Bogaerts’ 11-year, $280 million deal, adding to a star-studded cast that already includes Manny Machado, Juan Soto, Fernando Tatis Jr. and Yu Darvish.

One by one, free agents the Cubs targeted are signing with other teams, narrowing the potential paths for an 88-loss club to make substantial improvements and reach the playoffs next season. If the baseball operations group has so much money to spend that the president of business operations is talking about it on the radio, why did the Cubs pass on Christian Vázquez and Kodai Senga? Vázquez, a potential replacement for All-Star catcher Willson Contreras, received a three-year, $30 million commitment from the small-market Twins. Max Scherzer and Justin Verlander weren’t enough for Steve Cohen’s rotation, so the Mets landed Senga with a five-year, $75 million contract, betting on the Japanese pitcher’s potential.

The rampant frustrations on Cubs Twitter made this a good time to run a multi-part mailbag/airing of grievances. Questions have been lightly edited for length and clarity.

I was surprised by Kenney’s comments. Which of the two following scenarios do you believe is happening: Is ownership sick of being called cheap, and trying to pass the blame for no impact signing onto Hoyer? Or is ownership genuinely pushing Hoyer to sign a shortstop to a big contract and Hoyer is resisting? — Adam D.

It feels odd for Kenney to be so vocal all of a sudden about freedom to spend when the purse strings were tight the last few years. This seems like Kenney is trying to make Hoyer the fall guy if they don’t turn it around this year. Is there internal strife between Hoyer and Kenney or am I reading into it too much? — Brendan N.

Patrick Mooney: What might be unusual for most professional sports franchises is standard operating procedure in Wrigleyville. Kenney mentioned the rollover funds last summer during another appearance on The Score: “All the resources that weren’t used that would have pushed us up the ladder on the payroll chart this year will go into next year’s budget.” For example, the savings account that Theo Epstein once set up for baseball operations helped finance the Jon Lester contract after a failed bid to sign Masahiro Tanaka. It was also a customary practice for Epstein’s front office to set aside nearly $10 million for in-season additions around the trade deadline.

So are the Cubs carrying over money that could’ve been used to acquire a decent reliever or an impact player? Kenney, who will be entering his 30th season with the Cubs organization next year, is skilled in the art of workplace politics, rising from his position as a Tribune Co. lawyer to outlast changes at the ownership level and continue pitching big ideas to the Ricketts family. Kenney says things that make headlines, like the time that Bloomberg Businessweek quoted him saying: “Basically, my job is fill a wheelbarrow with money, take it to Theo’s office, and dump it.”

Hoyer is a student of history and familiar with wheelbarrow economics. Even when the Cubs appeared to be on the verge of a potential dynasty after the 2016 World Series, the franchise followed a formulaic plan in terms of revenues vs. expenses and budgeting for baseball operations, spending at a high level but not as aggressively as Cohen’s Mets are right now. When Hoyer replaced Epstein after the 2020 season, he inherited a budget crunch in baseball operations that factored into the decisions to trade Darvish to San Diego and release Kyle Schwarber rather than offer him a contract through the arbitration system.

Like every other executive in professional sports history, Hoyer will never be given unlimited resources. How ownership responded to those financial losses during the COVID-19 pandemic has to be taken into consideration here. Marquee Sports Network has not been the game-changer that Cubs officials promised. Wrigley Field attendance this year reached its lowest level since 1997 (excluding the limited 2020 and 2021 seasons).

The Cubs were still a top-10 team this year in terms of total attendance. The Walt Disney Co. recently closed a $900 million deal with Major League Baseball to acquire the remaining 15 percent of BAMTech, which should equal a massive payout to each of the 30 clubs. Ricketts effusively praised Hoyer’s rebuilding plan in September, saying “the ball’s in Jed’s court when it comes to how and where he puts financial resources to work.” The light didn’t suddenly turn green for Hoyer to spend as much as these ongoing conversations are moving in an obvious direction after the Cubs shed so many big-money players in recent seasons. Given all the intersecting investments in and around Wrigley Field, there is probably hope on the business side that Hoyer acts a little more irrationally this winter.

“There wasn’t a mandate,” Kenney told The Score. “The one beautiful thing about our ownership group is they don’t issue a lot of mandates. They urge and encourage us to think broadly, whether it’s about saving the stadium or building a better spring training home or improving what we’re doing in the Dominican or doing what we can with our media network to serve our fans better. But they’re not real big on mandates to do things. They leave that in our hands, mine on the business side and Jed’s on the baseball side.”

How much of the “intelligent spending” guidance is being driven by Hoyer? And how much is coming from Ricketts? Fair or not, it feels like the Cubs are the owners in a fantasy auction that is so focused on getting a good deal and good value that they end up missing out on all the best players. Sometimes, you’ve got to overpay, and it feels like thus far the Cubs haven’t been willing to be flexible in that regard. — Adam M.

It is frustrating to see other teams go all-in, even to the point of spending enormous amounts of money for redundancy at some positions. Was Hoyer’s front office thrown off by just how much “non-intelligent spending” has occurred during the offseason? Does “intelligent spending” need to be redefined, especially with teams like the Padres and Mets willing to spend whatever it takes to win? — Michael R.

Is there a disconnect between ownership and the front office in terms of available funds? — Chuck W.

Sahadev Sharma: This feels like a chicken-or-the-egg situation. Hoyer knows that he has a certain budget to work with and that his team isn’t just one or two players away. He seems more cautious about years than actual money. This team isn’t on the verge of greatness, but he’s also stated that he’s not interested in a long rebuild. So he needs to add players to get them close to contention. He then needs to trust that those players are still high quality when the team is supposedly great (2024? 2025?) or have them off or nearly off the books by then.

He has to think that way because he has an owner, like most teams, who isn’t going to spend nonstop to get whomever he wants. That’s not an excuse or a suggestion that more owners shouldn’t behave like Cohen, Peter Seidler and John Middleton have the last few offseasons. It’s just the reality of the situation. It seems like this is probably how Cohen will always act, but will Seidler or Middleton eventually stop spending so luxuriously? Perhaps. But they’re the main contributors to the current wild market, putting Hoyer in this situation.

But it’s not just on the Ricketts. Listening to him talk, it sounds like Hoyer values finding “intelligent” deals and believes there are certain times and certain players that you go out of your comfort zone for. There’s also the great Andrew Friedman quote that The Athletic’s Andy McCullough brought up the other day: “If you’re always rational about every free agent, you will finish third on every free agent.”

Hoyer can stick to his guns here. Maybe he’s waiting for his moment and doesn’t want to spend recklessly a year or two early. But there are some problems with that. One is that fans are going to be irate. Late in the summer and once again when the season was over, they were repeatedly told that building a competitive team for 2023 was the goal for this winter. That’s going to be hard to accomplish without a lot more movement.

The second issue, and a more important one (fans’ feelings matter, but they’re not what decides the team’s future performance): it’s terribly risky to assume that when you’re ready to spend, the players you want will be there. There’s a risk that you’ll get so bad that players won’t want to join your team unless you go even further out of your comfort zone with spending. There’s the risk that none of your prospects hit or they get hurt or take more time to develop.

That perfect time may never arrive. So perhaps it makes the most sense to act on what’s in front of you right now rather than hoping and expecting that just-right moment to arise.

How different do you think this organization would have looked in the past and present if the Guggenheim group bought the Cubs instead of the Ricketts? — Darrell H.

When are the Cubs going to start acting like a large-market team? — Dean S.

If we consider the Cubs to be one of the top four or five franchises in terms of market size and revenues, why are the Padres and Phillies able to spend big money on free agents while the Cubs can’t? — Scott T.

Mooney: The Cubs are absolutely able to spend huge amounts of money on free agents right now, but they have so far repeatedly declined to do the offseason’s biggest deals, which have been fast-tracked mostly by eager owners in San Diego and Philadelphia who think their teams are close to winning a championship.

Guggenheim Baseball Management has won one World Series during 11 seasons running the Dodgers. The Ricketts family has won one World Series during 13 seasons running the Cubs. Both ownership groups have overseen successful renovations to iconic stadiums. But that’s where the comparisons end for now. On the baseball side, the Dodgers became the model organization that Epstein once envisioned in Chicago, a collaborative enterprise that combines great scouting, player development and coaching with cutting-edge technology and enormous financial resources. On the business side, the Dodgers consistently invested in their major-league product to buy more credibility, maintain a competitive baseline and give extra time for their prospects and new initiatives to grow. The clearest example of ownership’s philosophy was the 2012 blockbuster trade with the Red Sox that required the Dodgers to absorb roughly $250 million in salaries to acquire Adrián González, Josh Beckett and Carl Crawford.

Someday, Cohen expects the Mets to run an efficient operation that closely resembles the Dodgers. But until the Mets reach that point, their owner will continue spending to cover up mistakes instead of tearing down the major-league roster for better draft picks and trade-deadline prospects. All that said, Ricketts is seen as a good guy to work for because he gives Hoyer the freedom to set the agenda in baseball operations, make investments for the future and execute personnel decisions without the kind of interference that Astros owner Jim Crane displayed in Houston.

“Tom takes a step back, which I think is appropriate, at least the way we view baseball operations,” Kenney told The Score. “We provide the budget toward the end of the fall. We say, ‘Here’s the surplus that’s available to sign players.’ And then Jed and his team do all the work, whether we’re going to strengthen our pitching, hitting, and what we’re going to do on the trade market. You have a game plan, but it’s like anything, right? You have a game plan, and then you get into the marketplace, and it doesn’t always go the way you think it will. But flexibility is there. I think we got to let this thing play out. I would say by the time we get a little past the Cubs Convention (in mid-January), we’ll know a lot more about what our club is going to look like.”

With zero major-league payroll commitments for 2027, could you please explain Hoyer’s trepidation about adding one big long-term salary to the books? How does he expect to win a World Series in the next five years without one known superstar? — Ann G.

Sharma: This is a solid question because it gets more into the baseball side of things, though it’s still tied to the economics involved. It’s been said over and over, but repeating it one more time can’t hurt: There’s no reason nearly every owner couldn’t act like Cohen. They choose not to for various reasons. That said, it’s best to try and break down what Hoyer is doing under realistic parameters.

Could Hoyer have afforded to give Correa 13 years and $350 million? Absolutely. According to Roster Resource, it would bring the Cubs’ luxury-tax payroll for 2023 to just under $205 million. The first luxury-tax threshold is $233 million. Let’s say that the first level is the limit for 2023 — it’s probably lower, but we can be bold for this example. They’d still have work to do for this season and beyond, of course. Maybe they could get it all done before reaching that first threshold.

If they do that, and assuming no extensions, as far as seven-digit salaries or higher go, next winter has Ian Happ, Jason Heyward and potentially Kyle Hendricks, Marcus Stroman, Yan Gomes and Bellinger coming off the books, or about $72 million. That’s a lot of money! And it should create a lot of flexibility.

But there are questions that Hoyer has to consider when handing out the deal. When does Correa’s contract begin holding Hoyer back from spending? A former top executive once said that if you’re not comfortable with that contract being a sunk cost immediately, you shouldn’t offer it. We don’t know exactly how Hoyer feels about Correa specifically, but there are legitimate concerns, particularly the fact that he’s already had back issues and hasn’t even turned 30. That’s not typically a great indicator of future health.

Hoyer also has to consider how many of those big contracts he can have on the books. Having one for 10 years means you better have an owner who won’t shrug his shoulders about the lack of spending because your younger, talented players start getting expensive through arbitration.

Take a look at the rest of the league and see how many teams have more than two players signed for more than seven years and an AAV above $20 million. The Dodgers only have one. The Mets don’t have more than two. According to Roster Resource, only the Yankees and Padres have three. Whether the executives who handed out those deals regret any of them or not is a separate matter.

The point is, every time Hoyer thinks about handing out such a deal, he has to ask himself: Is this the guy? And is now the time? There are reasonable arguments to be made on both ends here as far as that big deal and who should get it. If it were just about money — and not years — it would be pretty easy to wonder what in the world is happening right now.

The Cubs should never be afraid to hand out high-AAV deals for the right talents. But there are legitimate reasons why Hoyer is being cautious about years. Still, it doesn’t help Hoyer’s case with fans that he’s never handed out one of those deals while running baseball operations, and he hasn’t been a part of a front office that has done so since Heyward’s deal prior to the 2016 season. Until he does, it’s going to be hard for many to give him the benefit of the doubt.

(Top photo of Jed Hoyer and Tom Ricketts: Kamil Krzaczynski / USA Today)


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