Odd Country, this land of the middle-aged. One day you’re threading 65-yard passes off your back foot, and the next you’ve crossed some unseen border, and hair’s falling out or sprouting from strange places. That first colonoscopy, 54-year-old John Elway admits, was a marker. But the real jolt came five months ago, when he became a grandfather. “That’s the one,” he says, “where I said, ‘Wow, I am starting to get up there.’”
There have been other signs. Quarterback withdrawal—twitchy fingers and chronic second-guessing on Sunday—long ago gave way to a more generic yen. “I just wish I had that 25-year-old body,” Elway says. So he engages daily in the endless task of remaining fit. Today’s masochism involved abs work, the monotony of a stair-climb machine, and a final charge on the stationary bike. Still sweating, the top buttons of his dress shirt undone, the man behind the desk at the Broncos’ complex this December morning hardly looks like the most dynamic force in today’s NFL.
But he just might be. As Denver’s general manager, Elway has found the thrill of assembling a roster as cathartic as a Hall of Fame playing career capped by two Super Bowl titles. Inheriting a 4–12 roster in 2011, he gambled on coach John Fox, who was coming off a two-win season at Carolina, and the next year he bet the house on 35-year-old Peyton Manning.
In January, for the second year in a row, a scintillating regular season ended in postseason disappointment, this time a 24–13 defeat at the hands of the Colts. Last year a torching in the Super Bowl led Elway to spend $60 million on defensive talent. It’s not clear what steps he’ll take this time around, beyond a mutual parting of ways with Fox. Elway, says longtime NFL exec Ernie Accorsi, “hasn’t made any bad moves.”
Still, this workout thing—it’s got to be for a reason, right? Staying in shape, maintaining for the sake of maintaining? Please. For Elway, what’s the point if you’re not keeping score? He has always had to win, you see. Always.
Today’s routine was part of a competition. Elway is half of a team taking on three other pairs of Broncos personnel. Whichever drops the most body fat in six weeks wins. The problem: Elway is by far the oldest competitor and has been known to succumb to the rogue doughnut, the second glass of Pinot. When the competition ended on Dec. 1, Elway hadn’t pulled his weight. “I let our team down,” he says, “so the competition [was] continued until Dec. 31.”
He cackles when told that the maneuver shocked no one. Old teammates still complain that whenever Elway was losing at Pop-A-Shot or gin rummy, he changed the game to best two out of three. “If you’re beating him,” says his Stanford teammate Don Lonsinger, “he’s not going to bed.”
Since taking this job, Elway sleeps less. Time does that to a body. There’s also the fact that he feels far more responsibility—and far less control—than he did as a player. Come Sundays, all he can do is watch. The night before last year’s Super Bowl, Elway stared at the ceiling, thinking, “I’ve got a bad feeling.”
Being right was no consolation. The pasting embarrassed Elway. It stirred up echoes of his own nightmarish role in a 45-point loss to the 49ers in 1990—his third Super Bowl defeat. “They’ll never let me live this down,” Elway said that night, staring into a bathroom mirror.
Like most people, he has all but forgotten that version of himself. Two late-career Super Bowl wins, at 37 and 38, changed the conversation forever. Elway used to insist that he didn’t need a title to fulfill his promise. But he was lying. That became clear just before redemption. It was January 1997; the Broncos had built a 13–3 team that would seemingly give Elway his last best shot at a ring. Then Denver lost unexpectedly in the wildcard round. Afterward Elway went home, and when his twin sister, Jana, called, her voice did something to him. He’d never cried in front of his four children. But he did then. Says Elway: “I knew I was running out of time.”
The dreams started six months ago. John has found himself jerking awake because suddenly Jana is right there. “I look back now,” Elway says, “and I realize how much I miss her.”
His sister was born 11 minutes after him, on June 28, 1960, and she came closer than anyone to knowing what it was like to be John Elway. It wasn’t just that, early on, they shared a “twin” language, or laughed constantly and never fought. It was that when John got in trouble in kindergarten, Jana would cry for him. “She was almost my conscience,” he says. She was also his match in competitive fury, nearly killing herself trying to beat John at everything.
Their college-football-coach dad, Jack, had always wanted a son, and John became his sidekick, best friend, and project. By the time the twins reached high school, Jana had shaped into a tennis prospect while John had emerged as one of the greatest football talents ever.
At Stanford, John was physical greatness personified: fast and durable, with a cannon arm. Because he was so gifted, people forgot that he’d grown up with a man who had helped invent the spread offense and had coached defensive secondaries. Jack would pick apart his son’s performances, and the practice continued when he joined the Broncos as a scout in 1993. The Denver QBs and the offensive line would hit a local bar, and Jack would be there, Skyy vodka in hand. “All of a sudden you’d ask, ‘Where’d John go?’ ” says Keith Kartz, Elway’s longtime center. “And he’d be over in the corner talking football with his dad.”
Elway’s last two NFL seasons inverted all the disappointment of his first 14. For years he had operated with a second-rate supporting cast; now he had running back Terrell Davis, great receivers, a defense with cojones. Elway didn’t even play that well when he finally won a Super Bowl, against the Packers: 11 of 22, no TDs, one interception. But the numbers didn’t matter, only the sight of the old QB scrambling, hurtling through the air, helicoptered by three defenders, lunging for the game’s key first down.
Until the 1998 season Elway had missed only nine games due to injury. Then it began: His hamstring, then his back, and he missed four starts. It irked him, but his critics had nothing to say now. Elway had a newfound sense of ease as he limped his way to MVP accolades in his second Super Bowl win.
The second title confirmed a worldview that would infuse how he approached business, celebrity, parenting his four kids, and, later, running a team: Life is a pendulum. “If you have three here,” Elway says, raising a hand over his head, “you’re going to have three here,” lowering it under his desktop. “I think we all end up back at zero. The true challenges come from when you face adversity. How do you handle that?”
The idea of buying an Arena Football League team bubbled up after Elway finished playing in 1999 (after selling his five car dealerships for $82.5 million). But the project was pushed aside as he explored bigger scores. And now the pendulum swung the other way. Elway’s attempt to open a chain of upscale laundromats failed, as did MVP.com (a sports-merchandise venture with Michael Jordan and Wayne Gretzky) and a bid (with Broncos owner Pat Bowlen) to buy the Avalanche, the Nuggets, and the Pepsi Center. “Three plus, three minus,” Elway says. “We all end up back at zero.”
Then, in 2001 and 2002, his dad and twin were gone: Jack from a heart attack; Jana, at 42, from lung cancer. While she was fighting the disease, John pulled strings at Stanford to get his sister into clinical trials and bought her a townhouse after her marriage fell apart. During all this he was scrambling to join Bowlen and billionaire Stan Kroenke to create an Arena League team. In June 2002, Elway appeared at a press conference announcing the birth of the Colorado Crush. That same month he and his wife publicly acknowledged they were separating. “It was the roughest period he’s ever been through,” says Elway’s mother, Jan.
On July 23, John was told to rush to Stanford Hospital. Jana could barely breathe. As John sat with her, she whispered, “I just want to live.” Around 10 p.m. nurses wheeled Jana out of the room for a scan. The family stood in the hallway. As she passed by, Jana fiddled with her mask, trying to speak. John wanted her to keep it on. She kept tugging. “Put that back on!” he kept saying until finally there was a moment when the illness fell away. As the bed was wheeled down the hall, Jana’s eyes lit up and she raised her middle finger.
John had to laugh. And that’s how it ended: a man and his fading conscience, staring at each other.
Running a team is work, the criticism constant, the paperwork numbingly dull. But if anyone thought that Elway would take Arena football lightly as a new CEO, that didn’t last. For all his swagger, Elway turned out to be anything but an egotist. “I’ve always fought to stay off the pedestal,” he says. “I’ve got to make [everyone else] feel like I’m one of them. When they know their opinion is important, you’re going to get the best out of those people.”
The Crush’s inaugural season, in 2003, was a reality check. With an eye toward training Elway for a role with the Broncos, Bowlen viewed the Arena League as an ideal place to master the rudiments of salary cap, staff management, league relations. Michael Young, a former Broncos receiver who served as a Crush vice president, says Elway “wanted to sit in on ticket-sales meetings, go on corporate sales calls, understand how merchandising worked.” He even folded team T-shirts when necessary.
The Crush were terrible that first year, and that led Elway to a moment of truth: He had to fire coaches—friends—and it hurt. “It was toughest because of the closeness,” he says, “but it was probably the best learning experience I went through. Two years later we won the championship. I followed my gut, and it ended up being right.”
Elway talks about his gut often. “When I was playing,” he says, “I got a gut about the type of guys I wanted to be around, the type of coaches I wanted to be coached by. Following that gut, I created the philosophy that I’m going to attack this thing with.”
That helps explain why Elway is a good bet to win NFL Executive of the Year and why he’s been on a run. But even before the loss to the Colts, he knew the pendulum would hurtle back. Bowlen resigned in July because of Alzheimer’s disease. And Elway’s 24-year-old son, Jack, was arrested for assault after his girlfriend accused him of dragging her out of a car by her hair. Jack pleaded guilty to a lesser charge and was sentenced to a year’s probation and counseling. Elway radiates equanimity when asked about such a loaded subject. “A kid made a bad decision,” he says, “but he’ll learn from that.”
How can Elway be so sure? Something in the gut, maybe. A feel for things his own father instilled. It’s strange: Until recently, John had kept thoughts about his dad and sister at bay. Then Jana started showing up in his dreams. Two months ago Elway fell asleep and found himself in a room with a smiling Jack. That vision was enough to keep John charged for hours—and hopeful. Jack didn’t come close enough to touch. He didn’t say a word. Maybe next time, though.
This story is from the February 2015 issue of Fortune.