The perfect marriage in sports is Theo Epstein and the Cubs

Of all Theo Epstein’s great discoveries over this last half-decade, a sense of comfort may be his best find. This is not to be mistaken with complacency, because Epstein’s reality is far more focus and drive and obsession than it ever will be lounging in a chair, staring at what he created and guffawing as he pats himself on the back. Comfort is more about knowing who you are and where you belong.

Theo Epstein belongs in Chicago, with the Cubs, with the burden of 108 years on his ample shoulders, with the spoils of his work bearing fruit before him, with an owner who is just the best because he doesn’t allow his fandom to spill over into meddling, with a fan base that is ready to saint him even before he takes that century-long championship drought and pulverizes it. Which is no certain thing, remember, something that Epstein himself acknowledges during those nights he can’t help but wonder if what he has assembled is enough.

Even if it does happen this October – this machine the Cubs have built does to baseball in the final month what it did over the previous six – that wouldn’t so fulfill Epstein that he’d feel compelled to throw up deuces and peace it to retirement as the guy that killed two curses. No, comfort is symbiotic, and as much as Epstein has delivered Chicago, it has brought him so much, too, chief of all a reminder that when you strip away the focus and drive and obsession, this game is still fun as hell.

So when he agreed to a new five-year contract over the weekend with the Cubs that makes him the richest executive in baseball, and perhaps the most well-compensated in American sports, non-mindfulness guru division, Epstein did so without any animus that others may have harbored. There were no threats to leave, no posturing, no nonsense. Just Epstein and Cubs owner Tom Ricketts armed with mutual respect and the knowledge that both wanted a deal done in equal measures.

For Ricketts, signing Epstein – and also locking in general manager Jed Hoyer and personnel titan Jason McLeod, who with Epstein comprise the Cubs’ decision-making Cerberus – was obvious, even if it takes Chicago’s executive pay to the top of the industry. They won two World Series together and laid the foundation for another championship in Boston. They took the Cubs from last-place mess to this 100-win-plus juggernaut that’s well-positioned to win this year and the next five, too. Teams don’t let guys like that go. Well, except the San Francisco 49ers.

For Epstein, committing to the Cubs was obvious, even if the idea of cashing in for a deal that, with incentives, could reportedly approach $50 million feels weird. Like, that’s player money. Only he earned it, because the gravitas of his past accomplishments have allowed him to enjoy the present and prepare for the future. The Cubs have built a machine that goes well beyond the field. Keeping Epstein and Hoyer and McLeod is a coup, yes, but the Cubs’ front office will be poached. Pro scouting director Jared Porter will be a GM and soon. Shiraz Rehman and Jaron Madison deserve more than the typical thanks-for-coming blow-off minority candidates in baseball receive on the regular. Scott Harris isn’t even 30 and is on teams’ radars. Chris Moore is the inquisitive, incisive mind every organization covets.

This is what a team looks like, and to have built it from scratch, from the scrap heap Epstein inherited, with an old, broken-down major league roster and a minor league pipeline that had Javier Baez and the terrible, horrible, no-good, very-bad system. (Plus D.J. LeMahieu. Even Epstein whiffs sometimes.)

All of this led Ricketts to recognize the obvious: Epstein belongs in Chicago, not just to see this season through but to build upon what he’s built already. The Cubs are where they are because of the brilliance with which this team was constructed. An incentive to lose exists, though the Cubs played it well, spending enough money in free agency to grab assets that would give them some respectability during the lean rebuilding years but also function as trade bait later on. Anthony Rizzo came via trade. Same with Addison Russell. And Jake Arrieta. Kyle Hendricks, too. If you value a marginal win around $8 million or so, and figure combined they’ve been worth somewhere in the vicinity of 18 wins above replacement in 2016, this year alone that trade has been worth more than $140 million in value to the Cubs.

Some of this takes luck, sure. Kris Bryant slipped to the Cubs at No. 2 in 2013, and three years later he’s going to win National League MVP. Arrieta and Hendricks’ evolutions into Cy Young winner and ERA titlist is 99th-percentile stuff. Finding a manager like Joe Maddon is kismet.

Everything’s coming up Theo. In the minds of Cubs fans, it’s like they replaced the goat with the G.O.A.T., and now they’ve got him to finish what he started, in case the Cubs can’t do so this October. They’ll be the favorites, strong favorites, warranted favorites, and that still gives them, oh, a 30 percent chance of winning, maybe 35 on a good day. Short series are ruthless, and even the best team in baseball is at their mercy.

This is something with which Epstein has come to terms, frustrating though it may be, and part of that is getting older, part of it wiser, part of it more comfortable. Epstein always thought the Red Sox job was the best in the world, and in plenty of ways it was. He grew up near Fenway Park, found the work environment invigorating and fulfilling, relished in the breadth of their achievement and the depth of its meaning.

And yet Boston never really was his, not with ownership doing its meddlesome best to isolate Epstein and eventually facilitate his departure. The Red Sox didn’t do bad without him: History will look back on Ben Cherington’s tenure and wonder how with all he did the Red Sox possibly could’ve fired him, and Dave Dombrowski’s track record is undeniable. Still, the fairy tale says the kid belongs in his home.

The fairy tale isn’t wrong. It’s just that Theo Epstein has a new home. The Cubs reinvigorated him, reminded him of what the game means and what the pursuit of greatness entails. He and Chicago belong together, and for at least another half-decade he’ll be there, right where he belongs.