T

om Ricketts is standing on a ramp at the edge of Wrigley Field, outlining his vision for the neighborhood.

"There's the office building," says the Cubs' co-owner and chairman, pointing to the right in the muggy midsummer dusk. He draws his finger down to a spot just outside the stadium wall. "Everything below is going to be a club for the players." He says it all a little dreamily. "It's going to be the nicest clubhouse -- a big, circular clubhouse, and it will have the best weight room, the best training room, aquatherapy, all of that. That'll be here for the players who have suffered for a long time at Wrigley Field."

As Ricketts, 50, describes his plans for a plaza with a farmers market and a 175-room hotel across the street, it's hard not to think of a king surveying his imaginary kingdom. Right now, that best-in-the-business clubhouse he speaks of is nothing more than a hole in the ground. The office building is just a crosshatch of steel beams. The beautiful hotel is a McDonald's parking lot. "That'll be done in two years," Ricketts says, turning on one heel and bounding up the ramp toward the upper deck. Behind him, a lightning storm comes crackling toward Wrigley from the west.

No franchise in America better exemplifies the tension between baseball's business imperatives and its sentimental attachments than the Cubs, which has made transforming Wrigleyville a gargantuan task for Ricketts and his three siblings. But even that project seems small compared with their ultimate goal: When Tom, Laura, Todd and Pete Ricketts bought the team in 2009, they took on perhaps the most daunting challenge of any team owners -- ending the Cubs' World Series drought, now at 106 years and counting.

"We started right off the bat saying we're going to win a World Series," says Laura, 48. "And we're going to put a team on the field every year that can consistently compete for that."

To show they were serious, the siblings unveiled plans to modernize the stadium and committed to new spring training facilities in Arizona and a new baseball academy for player development in the Dominican Republic. Then in 2011, the Ricketts family brought in Theo Epstein, the front office wunderkind who led Boston to its first World Series title in 86 years, to run the team's baseball operations.

All of these projects were undertaken with a better future in mind, though perhaps even the Ricketts family didn't realize the future would arrive this quickly. The Cubs finished second to last in the NL Central from 2010 to 2012 and dead last in 2013 and 2014. But now, through a rocky and raucous 2015 season fueled by Epstein's inspiring collection of young talent, they seem closer to breaking the curse than they've been since at least 2008, when they were swept by the Dodgers in the first round of the playoffs. Two days after Tom Ricketts outlines his vision at this mid-August night game against the Tigers, the Cubs embark on a six-game winning streak. Then they lose four. Then Jake Arrieta pitches a no-hitter against the Dodgers and the team wins 13 of the next 19, opening a sizable lead in its pursuit of a wild-card spot. However this season turns out, the Cubs will be on the short list of top World Series contenders for 2016 -- and beyond.

Ricketts, who looks like Republican presidential candidate Ted Cruz in his game-day uniform (white dress shirt, khakis, Cubs staff badge), makes his way through the stadium, performing his Wrigley Field ritual. In one hand he holds a cinched bag filled with date-inscribed baseballs, and with the other he passes them out to kids. Grown men ask him for selfies; young men give him slapping handshakes. The kids who take his baseballs don't really know what to think and remember to thank him only when their parents nudge: "Now, what do you say to Mr. Ricketts?"

"Some kids are almost like: 'Why is this weird old man giving me this baseball?' " he says, making his way through the mess of people zipping from seats to concession stands and back again. But Ricketts, who manages the day-to-day running of the Cubs with Epstein and president of business operations Crane Kenney, sees handing out baseballs as one of his most important tasks. He started doing it five years ago to try to reassure fans that he and his family aren't simply a bunch of multimillionaires but people who love the team as much as anyone.

It's been a tough sell. The family embodies a heady mishmash of business and political ambitions, which sometimes contradict each other and occasionally clash in an explosive way. Most of the family members are high-powered conservatives operating in the Democratic stronghold of Chicago. Todd and Joe Ricketts, the family patriarch, run the Ending Spending Action Fund, a super PAC that opposes what it deems to be wasteful government spending and supports a number of high-profile Republican (and a couple of Democratic) politicians. Todd, 46, also served as the finance co-chair for Wisconsin governor Scott Walker's now-defunct presidential campaign. Pete, 51, was elected the governor of Nebraska as a Republican in 2014.

Laura, on the other hand, runs a super PAC called LPAC, which organizes lesbian donors and supports gay rights causes, and she was one of the bundlers who helped make President Barack Obama a financial powerhouse in the LGBT community. The siblings brush off questions about the potential for awkward dinner-table conversations around their divergent views. "I just say to people, 'Do you agree with everything your brother thinks? No,' " Laura told me in an interview earlier this year.

We're going to win a World Series. And we're going to put a team on the field every year that can consistently compete for that. - Laura Ricketts

Tonight, while Tom mingles his way through the upper deck, Laura and Todd sit behind home plate with Laura's 4-year-old daughter, Audrey, and her wife, Brooke. (Pete, the governor, makes it to the stadium less frequently these days.) Behind them sit Scottie Pippen and, a few seats down, supermodel Kate Upton, girlfriend of Tigers pitcher Justin Verlander and a friend of the Ricketts family.

Todd squints at the field and considers whether it's possible to enjoy the games like he did before he took on the responsibilities of ownership. (Tom is the only sibling who has a daily role on the team. Once a week, he holds a conference call with his siblings, who, along with a representative from the Tribune Company, make up the rest of the board.) "Mark Twain has a great quote in Life on the Mississippi, talking about when he became a riverboat captain. And the gist of it is, careful what you gain for what you lose," Todd says. "He talks about how he learned to read the river, and he lost a little bit of just enjoying the beauty of the river. I feel like sometimes I lose a bit of that, like, just pure passion."

But let's not get too sentimental here. He also wants to win. "When it happens, I think it'll be a celebration the likes of which we have never really seen in this country for any event."

Never been seen for any event?

"Yeah," he says. "And it's not going to be, like, a flip-over-the-cars-and-light-them-on-fire sort of party. I think it's going to be a happier event than that. It'll be big."

As Laura and Brooke talk about their June wedding -- they got married 20 days before the U.S. Supreme Court legalized same-sex marriage, capping off a battle Laura has been fighting in the Midwest for years -- phones begin buzzing with a weather alert. emergency flood warning in your area, seek shelter immediately. Just then, the lightning that's been rolling in for the past hour breaks, and water comes pouring out of the sky so fast and so heavy, it seems possible that it might flood Wrigley instantly. Fans, owners, basketball stars and supermodels go lurching toward the shelter of the concourse.