What did Theo know, and when did he know it?

He either left to help Jed, or because he knows it's all hopeless

What did Theo know, and when did he know it?

Theo Epstein’s final day with the Cubs was officially Friday, and I hope they scheduled a 4 p.m. meeting with Crane that he blew off. There are a lot of questions about the timing of Theo’s exit and what it means for the near-term future of the Cubs.

Basically, it boils down to two options.

Either he left now so that his successor, his friend Jed Hoyer, could have free reign to make the looming crucial decisions on what to do with all of the actual good players on the team in the final years of their contracts. There’s one thing for Theo to get Jed’s input into those decisions in his lame duck year, and it’s completely another for the guy who will have to live with the decisions to be the one who makes them.

This option is positive. It leaves you with the idea that Jed will get a decent player salary budget and it’ll be up to him to decide the future of his roster. In this one, there are a lot of Zoom calls with David Ross for his input, too. After all, “Rossy” (I just hate that awful Quade-esqe half-assed nickname) was brought in a year ago to change the clubhouse culture, so he should have a say in this too.

You will probably not be surprised to know that I think this option isn’t the one that’s actually happening.

Option two is that Theo got his hot little hands on the player salary budget for 2021 weeks ago, and went, “Fuck this,” and started planning to get out of the Gallagher Way.

If the budget, for the third year in a row doesn’t have enough in it to add the necessary complimentary players to the current core, what’s the point?

But what if the budget doesn’t even have enough in it to keep everybody they already have, much less add to it?

A couple of weeks ago the Cubs had to write $11 million worth of checks for Jon Lester and Daniel Descalso to not play for them next year.

I’m sure when the garbage family that owns the team sat down in a room with a whiteboard and somebody wrote on it that the team could save somewhere in the neighborhood of $30 million by not tendering contracts to the third baseman who had an OPS+ of 46 (100 is league average) and a rightfielder who had an OPS+ of 88, it piqued some interest.

I’m not against the Cubs making big changes to the roster. Hell, it clearly needs them, but there’s a big difference between trying to re-tool your team and being ordered to slash the payroll. We don’t know if Jed has to dramatically cut salary, but come on, I think we know that Jed has to dramatically cut salary.

The most tradeable Cubs, theoretically, include some really good players coming off lousy years (Kris Bryant, Kyle Schwarber, Javy Baez, Jose Martinez—hah, just wanted to see if you were paying attention) which isn’t ideal, and they are all free agents after this coming season which is even less ideal.

The assumption in the media has always been that Javy is the most likely to re-sign to a long term deal. But why? Because his agent isn’t Scott Boras, or because he’s Puerto Rican or something? I don’t know. My guess is that Javy likes money as much as anybody else, and is likely to sign for as much of it as possible. And, even if he were for whatever imaginary reason more likely to want to stay, if the Cubs dump Bryant and Schwarber and are going to let Rizzo walk, wouldn’t Javy just leave to go to a good team and get paid?

The Athletic has some good stuff on Theo the last few days, though I really miss their old Monday Cubs columnist. Whatever happened to that guy?

Jon Greenberg’s article on Theo’s departure featured this very self-aware take from Epstein about his ability to execute the necessary moves after his team has won.

“If you look at my track record in Boston and then here, in the first six years or so, we did some pretty epic things and then the last couple years weren’t as impressive,” Epstein said. “Maybe what that tells me is, I’m great at and really enjoy building and transformation and triumphing. Maybe I’m not as good and not as motivated by maintenance, so to speak.”

The other notable article they had was the one from yesterday that really just makes Theo seem like kind of a dick to hang out with.

The biggest difference though between his success in Boston and with the Cubs was that he took over a good Red Sox team that needed some key moves to put them over the top and in Chicago he inherited a goddamned mess that needed everything. That he excelled at both tasks is the reason he was a sure-fire Hall of Famer before his 43rd birthday.

But, he’s right about the second half of his terms in both cities showing diminishing returns. In Boston, turmoil within the ownership group (Larry Luccino being a dick, mostly) drove Theo to put on a gorilla costume and quit for a month or so (at which time Jed got to be be in charge, albeit in a time share with Ben Cherrington). And, some ill-advised free agent signings bloated the roster and payroll. When Cherrington took over for good when Theo left for the Cubs, the Dodgers willingness to take on most of the bad contracts in one trade saved them, at least after the forced marriage of Bobby Valentine ended after one season. Hey, did you know Bobby Valentine invented the wrap? Oh, never mind.

The Cubs don’t have a bunch of terrible contracts—pretty much just Jason Heyward’s—and in a better world Jef could use salary flexibility to his advantage given there will be a lot of teams trying to shed payroll this winter.

After all, this was going to be the year when all that sweet, sweet Marquee Sports Net money really flowed in. The pandemic will allow Crane some cover this coming season as it has masked just what a disastrous flop the long-awaited cash cow ended up being. But he won’t be able to hide that for long. Then again, if you rely on a streaming service the Cubs will effectively be hidden from you next year.

All that said, I do not expect that Epstein left because he was told the payroll couldn’t support the return of all three key arbitration guys (Bryant, Baez and Schwarber). I think he left because the ability to add onto the roster in any meaningful way is being hindered. And I do think the plan will be to run back most of last year’s roster and extend qualifying offers to Bryant and Baez in the offseason and try to sign Baez long term. I do not know why Javy would sign one, but if he refuses to make any in season batting approach changes again next year, he’ll be doing them a favor.

I expect Jed will be fielding offers at the deadline for Bryant whether the Cubs are in contention or not in a last ditch effort to salvage more than a single compensation pick for him. And, I think it’s possible, though unlikely that a team makes a bona fide attractive offer for Bryant or Schwarber this winter, and that the Cubs would be more than willing to do something with either or both.

I’m sure Schwarber won’t want to leave. What other team could he play for where he can just walk out the left field gate and go play fireman?

Given the financial uncertainties for the entire league I just don’t see much in the way of teams adding meaningful salary happening. The Mets will try, but who else? The trades we get will mostly be a shuffling of big contracts for each other. I just don’t see teams out there willing to take on much more than they offload.

Then again, I think there’s a fair chance Spring Training starts late and the season has fewer than 162 games in it.

So the Cubs are going to try to be just good enough to not be bad, again.

Here’s the part where I can’t resist the urge to remind us all (as if we needed it) that the Cubs financial constraints are completely by their own choice. Only by virtue of creative accounting in their favor have they been able to pretend to be making only modest profits the last five years. I’m sure they lost money last year, and you know what? Tough shit, we all lost money this last year. But unlike them, nobody else’s daddy sold the family business for $26 billion dollars. Even after they finally put the money back in the grandkids college fund they had a little left over. I’ve seen what tuition and board at the University of Nebraska is. And how much could it possibly cost to send Todd’s kids to Full Sail University?

The biggest hindrances to the Cubs’ willingness to spend what it takes to win the World Series are these:

  1. They won one, which we all loved and still love, but they can just point to that to remind everybody they already checked that box. This does not seem like a family driven to win at all costs unless forcing meatpackers to work in a pandemic is the win they’re looking for.
  2. They are the only big market team in their division. Major League Baseball likes to remind us that St. Louis isn’t a large market by giving them extra draft picks and shit, and nobody can even pretend that Milwaukee, Cincinnati and Pissburgh aren’t dying rust belt cities. The Cubs whole goal will simply be to be in contention within the division. That’s not going to cut it in a league with the Dodgers. Spending to win 92 games in the NL Central and spending to win a pennant are not the same thing.
  3. If playoff expansion is really here to stay then they won’t even bother to spend to that level, they’ll be content to spend at a level commensurate with having a record in the top half of the National League. Whoo, dare to dream. You want an example of how that works? The Indians have been working it since 2017. They kept shedding players and trying to find the sweet spot that would allow them to save money and delude their fans with a team that’s in the “playoff hunt.”

The biggest threats to the Cubs returning to the pre-Theo days aren’t their stunning lack of success developing pitching, or hitters that insist on trying to blast ground balls right into the shift. It’s an ownership that knows they can return to selling hope to fans over results. Hope’s a hell of a lot cheaper to buy than actual wins are. And as the league makes getting into the playoffs easier, it becomes easier for the Ricketts to hide behind useless shit like, “we’ve made the playoffs five out of the last six seasons.” That stat would have meant a hell of a lot more if it happened in the ‘60s or the ‘80s.

The reasons Theo left when he did will become apparent soon enough. Because only then will we find out what Theo knew, and when did he know it.