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?"

Cubs' renaissance started at the top

Cubs owner Tom Ricketts, who was a bleacher bum before buying the team with his siblings, discusses the approach to rebuilding both the team and iconic Wrigley Field.

"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.

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.

FIFTEEN MINUTES LATER, Upton is holding court at a table in a Wrigley box suite as Tom Ricketts buzzes around the room ordering drinks for guests and conferring with staff about the rain. Laura and her family went home when the storm broke, but around the table are Todd Ricketts; Upton's cousin and their friends; Brian Baker, who helps run the Ending Spending super PAC; Charlie Spies, who was chief financial officer for Mitt Romney's 2008 presidential bid; and airplane pilots who are there to fly vintage P-51 Mustangs over Wrigley the next night. Upton is telling a story about her boyfriend, Verlander, at his career low point in 2014.

"It was my birthday, and he had probably like his worst game ever, and no one had any idea how he'd respond to his worst game ever," Upton says. "He vented to me in the car and was like, 'I am going to get blackout drunk.' So a bunch of us went out and got blackout drunk! I had really good plans to eat popcorn and watch a movie, but he was like, 'I don't want to think about it, at all.' "

Later, Upton recounts how she became friends with the Ricketts family on her 21st birthday two years ago. Standing in the elevator of her New York apartment building, she heard a voice that sounded like her dad's making jokes about hitting all of the buttons on the elevator before they got off at their floor. "I was like, 'God, he's making stupid jokes. He's so annoying.' " Then she looked up and realized the man was her uncle, Fred Upton. "I was like, 'Uncle Fred! I'm related to you.' " Her uncle, a Republican congressman from Michigan, was in town for a meeting with the Ricketts family. Kate went to her apartment, threw on some clothes and joined the party.

"And I had to help her out of the elevator when she came home from the club," Todd adds.

"Yeah, I was throwing up at his parents' house. It was so embarrassing," she says. "Just kidding!"

This is the kind of gathering that could be plausibly hosted only by the politically connected mega-rich -- hardly a scene the Ricketts kids were used to until very recently. They grew up as the poorer kids in a nice neighborhood in Omaha, Nebraska, the children of a small-business owner who went to college only because his father told him he'd never make it in the family carpentry trade. Their mom, Marlene, a sarcastic, baseball-loving teacher, quit her job to work for her husband's experimental new brokerage firm, which later became the first to allow customers to make trades using their touch-tone phones. They furnished the house creatively, using discount office furniture in the dining room and plastic tablecloths as curtains. The boys had paper routes and fast-food service jobs. Weekends, according to the stern patriarch, were not for cartoons but for chores.

After high school, the kids made their way to Chicago for college: Pete, Tom and Laura to the University of Chicago, Todd to Loyola University. One by one, they fell in love with the city, which meant falling in love with the Cubs -- with the party atmosphere of Wrigley's center-field bleachers, with the belief that cheering for the lovable losers was their civic duty. Tom and Laura met their future wives there. In 1990, when Tom and Pete were sharing an apartment above a sports bar across the street from the stadium, Tom wrote on his business school application that his dream job was to own a major league baseball team. "But as I'll never have a hundred million dollars, it might be a minor league baseball team," he remembers writing.

Seven years later, Ameritrade went public, and the Rickettses became one of the wealthiest families in America. A decade after that, when the Tribune Company began signaling that it might sell the Cubs, the possibility of owning a major league team didn't seem so ridiculous anymore.

When his kids first floated the idea, Joe could hardly imagine having the patience to sit through a game, let alone run a team as desperately in need of revamping as the Cubs. So they took him to one of the rooftop bleacher businesses overlooking the stadium, hoping to impress him with the view. They pitched the purchase as an opportunity to do something meaningful -- something ambitious -- and to do it as a family. That convinced him. After putting together a team of advisers and going through what Joe called "the most complicated deal I've ever seen," the Ricketts siblings, using a family trust and acquiring a lot of debt, bought the team and Wrigley Field for $845 million in October 2009.

At first, the Rickettses were seen in Chicago as saviors -- human, Cubs-loving faces in place of a corporate ownership group that had been in financial trouble for years and had taken the team to the playoffs just six times in its 28-year tenure. But as the Cubs kept losing and the family's political and business interests crossed streams with the team's venerable traditions, they began to encounter opposition.

The siblings knew they'd need to renovate Wrigley, whose beloved reputation belied out-of-date facilities. But the stadium, built in 1914, was designated a historic landmark more than a decade ago, meaning many changes would have to go through a complex approval process involving a local commission, an alderman and the mayor's office. It's an unusual situation in professional sports: The Ricketts family owns the facility in which its team plays, but it's uniquely beholden to the city and neighborhood.

Initially, the family asked to use public funds, first from the state and then from city amusement tax revenues, to help pay for upgrades. But during the 2012 presidential campaign, The New York Times reported that Joe Ricketts was considering a proposal for a $10 million investment to fund a series of ads meant to tie Obama to his controversial former pastor in Chicago, Jeremiah Wright. Although Joe said he never intended to go forward with the plan, prominent city Democrats -- the people the Ricketts family needed to approve its funding request -- were furious. An aide to Mayor Rahm Emanuel, Obama's former chief of staff, said Emanuel was "livid" that the family would dare ask for money for the Cubs -- in the midst of a budget crisis, no less! -- while considering a $10 million smear campaign. Tom Ricketts tried to point out that his dad wasn't the owner of the team, but it wasn't enough: The proposal to spend public funds was dead. The renovations are now being privately funded, with a little help from new investors.

Meanwhile, the family brought a business school mentality that some longtime staffers felt failed to appreciate their institutional knowledge. Says one former employee: "We had a line around the office that went something like, 'We used to be run by a large corporation that felt like a family; now we're run by a family that feels like a large corporation.' "

The rooftop bleachers presented another set of challenges. In 2004, under the Tribune's ownership, the Cubs and most of the rooftop owners came to an agreement: The businesses would turn over 17 percent of their profits in exchange for a promise that their views into Wrigley would remain for the next 20 years. But not long after the Ricketts family bought the team, the Cubs complained -- privately and publicly -- that the rooftop businesses were siphoning money from the franchise, according to a lawsuit filed by the rooftop owners earlier this year. The Rickettses' renovation plan included expanding Wrigley's own bleachers and adding large video boards to generate revenue, which would have blocked some views. The family tried to buy some of the properties and, the suit claims, threatened that it would further block the views if the owners failed to sell. After several rounds of back and forth, the team won approval from the city to move forward with its renovations. Tom Ricketts initially said he wouldn't proceed without a guarantee from the rooftop owners that they wouldn't sue, but when those talks failed, he said the club would move forward anyway. "My family's plans for Wrigley Field have gotten lost in a dispute with the rooftops," he said in a May 2014 video addressed to fans. "We cannot delay any longer. The time to build a winner is now."

The video stoked a sense that the Ricketts family was conflating renovating the stadium with winning a World Series -- as though one would necessarily follow the other -- and portraying those who disagreed with the plan as a roadblock on the path to a championship. The tension wasn't helped by the fact that the Cubs were playing terribly and stadium attendance had dropped. (It might or might not have been a coincidence that in 2013, in the midst of the standoff, a severed goat's head addressed to Tom Ricketts was delivered to Wrigley Field.)

Since then, the Ricketts family has moved ahead with its renovation plans and bought six of the rooftop buildings, most recently three in May. A judge rejected a request by the rooftop owners to halt construction of a video board in right field, though the broader suit is still pending in federal court. Relations are calmer now, but Jim Spencer, president of the East Lakeview Neighbors Association, says there's "a very strong sense of wariness or distrust" about the team's intentions for the neighborhood. "Their plans, I would say, are attractive -- it does look like they're making some much-needed and widely appreciated aesthetic improvements," Spencer says. But he adds, "I don't (think they care about the neighborhood."

TO PASS TIME in the suite during the rain delay, Todd entertains Upton and her entourage with tales of his turn on Undercover Boss, a CBS reality show in which executives don disguises and try their hand at the most menial tasks needed to make their businesses run. When Todd was on the show, he says, he was amazed at how easy it was to disguise the fact that he was a co-owner. "I had a beard, and I was wearing these glasses," he says, lifting an old pair of Ray-Bans from the bridge of his nose, "and a Cubs shirt."

"I need that disguise!" Upton says.

"It's simple," one of the men teases her. "Just don't shave your face."

"I have a start!" she jokes. "I have a little upper lip hair. I have to wax it a bit."

"I do all sorts of manscaping," Todd responds.

Baker, the political aide and protector of the Ricketts brand, steps in to try to shut him up. "All right, all right, all right!" he says. "That's what we don't need."

But Todd isn't finished. He has a vision for this article, one he brings up more than once. He's even written his own headline: "Cubs owner Todd Ricketts and his good friend Kate in the Owners' Body Issue." He says to Upton: "Will you do that with me?"

"Sure!" she says. "100 percent!" They high-five.

It goes on like this for more than two hours, as the rain pours and the conversation drifts from Undercover Boss to the perils and paradoxes of online dating to when the players might get back onto the field. Tom Ricketts hovers on the edge of the crowd and takes it all in. "Once you make a rain-delay friend," he says, "you're friends for life."

The Ricketts spent huge money on Joe Maddon, Theo Epstein and young talent such as Starlin Castro (top). Andrew Nelles/AP Images

BY 10:30, THE clouds finally break, and what remains of the crowd heads back to the seats for the last six innings. The Cubs are losing, but as we sit on damp seats amid beer cups filled with rainwater, Tom is the only one who seems really concerned.

In this season of hope, a loss might not hurt as much as it used to. Through a combination of business savvy, genuine love for the team and enormous piles of cash, the Ricketts family is winning. It's getting its renovations. Ticket sales are back on the rise. And thanks to Epstein's youth movement, the team is doing well. Increasingly, the critics' grumbling must be done under their breath. Of the many neighbors, former employees and city officials I contacted who have butted heads with the family, nearly all refused to talk on the record -- no one wants to be seen as hating the Cubs when they're winning.

"When we took ownership of the team, we were the new thing that was unknown to everybody," Todd says. "We were really the thing that people wanted to see and get to know. And there's been a natural transition from us being the story to Theo being the story, and now players are the story. And I think that's a much more natural position for the team to be in."

"We've always felt like owners should be seen and not heard," Tom adds. "At first, we had to make sure everyone knew that we had a plan. That was the biggest question I got the first year: What's our plan? And then, once the plan was in place, to explain what that plan was and then just to execute it."

By now, it's past midnight, and the Tigers are on the brink of winning. We're all several beers deep. I get up to go to the bathroom, but Todd tells me to be patient. There is no way I can be that patient.

"OK," he says as I scoot past him. "But if you've come back and we've won, don't be surprised."

A few moments later, I hear the announcer call the end of the game. The Cubs, of course, haven't won. By the time I make it back to our seats, the Ricketts brothers are already gone into the night.

They are not the type of people to dwell on a loss.