Surpassing Michael Jordan as ultimate GOAT is Tom Brady's last challenge

Does Brady believe he has surpassed Montana? (2:17)

Ian O'Connor discusses his recent conversation with Tom Brady, including whether Brady thinks he is the greatest quarterback of all time. (2:17)

Tom Brady is running dangerously low on challenges, on opponents to identify and conquer, and this is what happens when a man has five Super Bowl rings and no other quarterback has more than four. Brady is always on the hunt, right? So why shouldn't he celebrate his 40th birthday in August and then start taking on the Madden curse in September?

But the tests don't end there. In an interview with ESPN.com, the 39-year-old Brady said he might play into his late 40s, never mind his mid-40s, and there really will be nobody left for him to topple the next six, seven, eight seasons but Michael Jeffrey Jordan -- the presumed greatest American team-sport athlete ever. Brady has a better chance than LeBron James of seizing that crown. He holds a 5-3 lead over James in titles, and the New England Patriots won't have to face the Golden State Warriors over the balance of Brady's prime.

"I was in awe of Michael Jordan," Brady said, "and I still am in awe of what he was and what he meant. ... He was such an effortless player. He put a lot of effort in, but there's an art and a beauty to the way he played the game. That was a very inspiring thing."

Of course, Brady would never publicly declare himself a player in Jordan's league. But he knew what he was doing when he agreed to play cover boy for the "Madden NFL 18" game under the title "G.O.A.T. Edition." Brady was notarizing the idea that he's the greatest of all time at the most indispensable position in the most popular sport, a truth that puts him squarely in the broader GOAT conversation. Squarely in Jordan's league.

Despite the biblical plague of locusts that visited much younger Madden cover men, Brady's history says the 2017 NFL season will be to this curse what the 2004 American League Championship Series was to the Curse of the Bambino. His history also says he'll play at a higher level beyond his 40th birthday, on Aug. 3, than anyone before him in any contact sport. He maintained in the 45-minute phone interview that time is on his side.

"I always said my mid-40s," Brady said of the prospect of retirement, "and naturally that means around 45. If I get there and I still feel like I do today, I don't see why I wouldn't want to continue."

Continue until 46, 47, 48, who knows? Brady brought up his wife, Gisele Bundchen. You know her as a supermodel, and maybe as the woman who once wanted to deck that taunting New York Giants fan who advised her that Eli Manning owned her husband.

"My wife says lots of things sometimes," Brady continued through the faint trace of a chuckle. "She makes decisions for our family that I've got to deal with. Hopefully she never says, 'Look, this has to be it.' ... My wife and my kids, it's a big investment of their time and energy, too."

But Gisele has signed off on his mid-40s, right?

"She wants me to do that, too," Brady confirmed. "She also wants me to take good care of myself and still have my energy. My kids have grown up faster than I thought."

Surely, any loving wife would want her loving husband to leave a hazardous profession with his body and mind intact, allowing their children to grow up with their father whole. Then again, if anyone knows what it means to get to the top of a profession and stay there for a long time, it's Gisele Bundchen. Forbes reported Bundchen has earned more money than any other model every year since 2002, and that last year she cleared $30 million -- or $20 million more than the second-highest earner, Adriana Lima.

Bundchen's dynasty is more impressive than Brady's, and frankly, it's easier to imagine her advising him to continue competing than it is to picture her telling him to hang it up.

Brady is Benjamin Button, after all. He looks more nimble in the pocket now than he did 10 years ago, and through fitness programs and plant-based diets that would make men half his age puke, he has inspired some otherwise crazy questions about his durability.

Like this one: Who says Tom Brady can't play in the NFL at age 50?

"That's a great question," he said. "If you said 50, then you can say 60, too, then 70. I think 45 is a pretty good number for right now. I know the effort it takes to be 40. ... My love for the sport will never go away. I don't think at 45 it will go away. At some point, everybody moves on. Some people don't do it on their terms. I feel I want it to be on my terms. I've got to make appropriate choices on how to do that, how to put myself in the best position to reach my long-term goals."

With private and distant superstars like Brady, it's useful to examine not what they say in the public arena, but what they don't say. The quarterback was asked if he could still be running New England's huddle at 50, and he didn't say, "You must be crazy." He didn't say, "What have you been smoking?"

He didn't say, "No."

Brady did say he wants to go out his way, which is another way of telling people he doesn't want to be traded or cut by coach Bill Belichick, or run out of town by the news media or the fans. But the dimpled leading man knows how this movie usually ends. Jordan and Babe Ruth, signature athletes of the 20th century, finished their careers as severely diminished icons in the unworthy colors of the Washington Wizards and Boston Braves before being forced out by their bosses, Abe Pollin and Emil Fuchs, respectively.

Joe Montana, Brady's boyhood idol, was dealt to the Kansas City Chiefs so the San Francisco 49ers could clear room for Steve Young. Montana had been motivated by Young's presence, and openly annoyed by it, too. Brady was asked if he is annoyed Belichick hasn't traded Jimmy Garoppolo, a second-round pick in 2014, keeping alive the possibility -- however remote -- that the Patriots might dispatch Brady in the not-too-distant future to make Garoppolo their Steve Young.

"When you're a member of a team sport, the best guy plays," Brady said. "So I always want to make sure I'm the best guy, and I give our team a great chance to win. But if you're ever not [the best guy], part of being a great teammate is letting the other guy do that, as well. Competition is what has always driven me. I've never been one that was hand selected, to be this particular player. ... In high school, college, professionally, I think the greater the competition, the more that it really allows me to dig deep and bring the best out of me."

Once again, Brady didn't say, "No."

For those old enough to remember, his response sounded like something that might've been said by Jordan, the self-described competition junkie who never met a real or imagined slight he wouldn't use to his advantage while winning six titles with the Chicago Bulls. And this is where Brady's last great challenge begins to take shape. His staggering comeback victory over the Atlanta Falcons in Super Bowl LI ended the debate over whether he's a better quarterback than Montana (5-4 in rings, 7-4 in conference championships, 208-133 in regular-season and postseason victories) and whether he's the best NFL player ever. Brady overwhelms Jim Brown with sheer volume (271 games played and counting to Brown's 122). Ditto for Lawrence Taylor (199 games played). If Jerry Rice wins on that front (332 games), Brady, the once-loyal Niners fan, could remind you (not that he would) that Montana had already won two rings before Rice was drafted.

So Brady was asked the following question: If you're not the best NFL player ever, who is? His pause was so long you could've counted one Miss-iss-ippi, two Miss-iss-ippi, three Miss-iss-ippi before he finally responded.

"I don't remember a lot of those guys like Jim Brown playing," Brady said. "I remember Lawrence Taylor, obviously; he terrorized the 49ers. ... I know that I haven't played against a lot of those guys, but I've also played against a lot of guys that when I think of Peyton Manning and Marvin Harrison and Dwight Freeney and Jason Taylor and Ray Lewis and Ed Reed and Darrelle Revis -- if those guys aren't the best, then whoever is better than them is only better by percentage points. It's not a big difference. So, like Deion Sanders, for example. I remember watching him play, how spectacular he was. But I can't imagine someone that much better than Revis. If there were, you couldn't complete a ball against Darrelle. So completing a ball against Deion is not much different than completing a ball against Darrelle."

Brady was asked if he'd at least concede what his Madden title stated -- that he has replaced Montana as the GOAT of quarterbacks.

"I don't agree with that," he said, "and I'll tell you why. I know myself as a player. I'm really a product of what I've been around, who I was coached by, what I played against, in the era I played in. I really believe if a lot of people were in my shoes they could accomplish the same kinds of things. So I've been very fortunate. ... I don't ever want to be the weak link."

The weak link? You're kidding, right?

"I was the backup quarterback on an 0-8 team in my freshman year of high school," Brady continued. "I got to Michigan, I was seventh [string], and I had a hard time getting to be No. 2, and when I finally got to No. 1 there was someone else [Drew Henson] they wanted to be No. 1. I got to be a sixth-round pick behind a great player, Drew Bledsoe, and then I got an opportunity, and I'm still trying to take advantage of it. Part of who I am now is very much who I was, and that was cultivated growing up."

Truth is Brady has already overtaken Jordan on this front -- the growing-up front. The backstory. Despite the mythology that he himself propagated, Jordan was never cut from his Laney High basketball team in Wilmington, North Carolina; he was merely kept on the junior varsity as a 5-foot-10 sophomore by a varsity coach who had a lot of returning seniors and who wanted Jordan to get a little seasoning by dominating the JV.

Brady? There's no mythology involved in his long-shot tale. The very first football coach to believe in him can attest to that.

Brady's humble beginnings

On Sept. 4, 1992, when Junipero Serra High School of San Mateo, California, played Pinole Valley High in a junior varsity scrimmage, a 15-year-old sophomore named Tommy Brady started at quarterback for the first time in his life. Thank heavens it was an informal, situational scrimmage and they didn't keep score.

"It was a disaster," recalled Serra's JV coach Joe Hession. "Tommy must've been sacked 15 times. ... We didn't score a touchdown and they ran all over us. It was the worst beating of my life, and it made you want to walk off and go to a bar and quit."

Hession didn't quit, and neither did Brady. They made it to the West Catholic Athletic League championship game that year at Bellarmine College Preparatory, and they were driving late for the winning touchdown when suddenly the automatic sprinkler system turned on -- twice -- causing a delay and leading to a Brady fumble of a wet football that cost Serra the title.

It's hard to believe Brady even made it to that sophomore year with a chance to be a starting quarterback. As a freshman on Joe O'Connor's winless team, he sat behind his close friend Kevin Krystofiak, who was a faster, superior athlete. Serra scored two touchdowns all year, and Brady still couldn't take the first-string job.

"I don't think we were ever in competition," Krystofiak recalled. "The job was mine. Even though we were struggling mightily, it was not a question that I would be removed from the position."

Brady got his first big break when Krystofiak quit football to focus on basketball. But when Tommy showed up for JV practice as a sophomore, standing at about 6-1 and cutting a pear-shaped figure, Hession looked up him up and down and figured he would make a good offensive tackle.

"We were looking for a quarterback," Hession said, "and he volunteered to give it a try. We had four or five other guys we were looking at, but as soon as you saw him throw the ball, you could tell he had something."

And then Pinole Valley beat the hell out of him, and the JV coaches walked off the field wondering if they'd duplicate the freshmen's winless season the previous year. Only one positive development stuck with Hession that day: Every time Brady got drilled, he quickly rose to his feet and returned to the huddle. "So we really never thought about anyone else," Hession said. "We were going to win or lose with Tom."

He kept getting better and better, and Hession was blown away by the detailed questions Brady would forever ask about technique and schemes, questions the coach often couldn't answer. Brady would go on to win only half of his 10 games as a senior, but constant footwork and jump-rope drills made him a Division I player. So did his unyielding quest for knowledge. The team would watch film on Saturdays after their Friday night games, and the next morning Brady would invite fellow receivers John Kirby and Giovanni Toccagino to his home for a closer look at every pass play in an attempt to improve their chemistry. "Nobody was doing that back then," Kirby said.

"If I get [to age 45] and I still feel like I do today, I don't see why I wouldn't want to continue."
Patriots QB Tom Brady, on his desire to keep competing

Brady was still considered a better baseball player -- as a left-handed-hitting catcher with power, he would be drafted by the Montreal Expos in the 18th round. When he decided to play football at Michigan, some of the Serra coaches were worried. They thought he'd have a better chance to move up the depth chart quickly at California or San Jose State. Brady assured everyone he would work his way into the lineup in Ann Arbor one way or another. "I remember talking to Tom about it," Hession said, "and I was thinking, 'Is he overconfident about this whole thing?' "

Done coaching football and golf, Hession, 62, remains at Serra as an English teacher, and he said he has tried to lay low nationally over the years because Brady "just fell into my lap." But the first head football coach to ever start Brady has some insight into why the quarterback survived his maddening experience at Michigan, why he nearly transferred but didn't and why he finally outdueled Drew Henson and won over Lloyd Carr and shredded Alabama in the Orange Bowl in his last collegiate game. Hession played golf with Brady and taught him how to surf the Pacific waves.

"And he comes off as a mellow guy where you don't see that drive, that competitiveness, until you get him on the field," Hession said. "He'd say when we golfed, 'Yeah, let's go hit a few balls,' and then once you start playing, he's trying to win every hole. Same thing with surfing. We'd pull up and he'd start asking questions. 'Where's the swell coming from? How do you catch the biggest wave?' He's 15 years old and I'm teaching him to surf and I'm like, 'Tom, just get on your wet suit.'

"He became a good surfer, but he got pummeled a few times by those waves. I could've ruined the greatest quarterback of all time, but he survived those lessons. And every time he got knocked off, Tom got right back on. He was never afraid. He had that look in his eyes that said he couldn't wait to catch another one of those big waves."

'Football is more than just what I do. It consumes me'

The last time Tom Brady was seen in a locker room, he was frantically searching for his jersey. He'd just erased a 28-3 deficit, and the memory of his brutal pick-six, to steal Super Bowl LI from the Falcons before realizing someone had the audacity to steal his stained jersey out of his bag. Someone had violated the perfectionist's perfect night.

Authorities in Mexico eventually recovered the jersey and another Brady jersey from Super Bowl XLIX in the possession of a credentialed journalist, Martin Mauricio Ortega, who reportedly wasn't charged with a crime. Brady was asked if he would like to see the man punished.

"I really don't like anyone to ever get in trouble," he said. "To me, I'm just happy I was able to get it back. ... My reaction then wasn't heartbroken. I thought, at the end of the day, it was a jersey."

Brady mentioned he'd like to find time at some point to "give something back" to the authorities who worked so diligently to retrieve his property. He was asked again if he'd like to see Ortega jailed.

"No, absolutely not," Brady said. "I don't like conflict. It's just inherent in who I am."

It's possible Brady was too emotionally drained to engage in another fight. He'd just played the longest and shortest season of his NFL life at the same time, his schedule reduced by his four-game Deflategate suspension and yet his stress level dramatically increased by his mother's fight with cancer. Tommy is the baby of his family, and his three older sisters are terrific athletes. Galynn Brady and Tom Brady Sr. spent their lives shuttling their kids from gym to field to practice to game. They even traveled to Michigan games when Tommy had as much chance of getting under center as his old man did.

Only there were no Patriots games to attend this season. "It was the first year in all the years I've played sports," Brady said, "where it really wasn't their choice to come or not come. ... I kept saying, 'Mom, you've got to take care of yourself. Dad, you've got to take care of yourself.' They should be taken care of. I was happy they were able to be at home and not deal with flights and not deal with a lot of stress from the games. They wanted to come at different times. I said, 'Don't worry, Mom, we're going to get you to Houston.' She really set her sights on that as her treatment was coming to an end."

Brady said he greatly appreciated his owner, Robert Kraft, and his receiver Julian Edelman telling him they needed to win it all for his mother. After leaving NRG Stadium the night of the Super Bowl, Brady found a corner room at the Patriots' massive postgame party -- "Away from all the chaos," he said -- to share a private moment with his parents, his sisters and his wife. Brady had his first meaningful postgame conversation with his mother in that room. "I don't remember exactly what we said, but it was very emotional," Brady said. "It was a great night, just for her to be there."

The whole scene in Houston felt like the culmination of an epic career. Brady took the Lombardi and MVP trophies from the commissioner (Roger Goodell) who suspended him, wrapping a beautiful bow around a season that started in Week 5 in Cleveland, where he was running wind sprints with a resistance band wrapped around his waist outside the Patriots' locker room an hour before kickoff. Only Brady.

So what possibly could be left to accomplish? Brady still has his medicine man, Alex Guerrero, by his side, keeping him young with his famously fun-free workouts, sleep schedules and meal plans. (Brady said he does eat the occasional cheeseburger. "I'm just not going to do that five nights a week," he said, "not if I want to keep playing football at a high level.")

He still has Belichick, 65, as hungry as his quarterback. He still has a stacked roster that was just made more dynamic with the addition of Brandin Cooks, whom the quarterback was careful not to anoint as his next Randy Moss. ("Your role is whatever you make of it," Brady said, quoting Belichick. "The more you do to help the team win, the more of a role you'll have.") More than anything, Brady still has that maniacal desire to compete.

"I think there are many more players blessed with more ability," he said. "I've worked hard with what I've been given ... and I've had to go about making improvements in different ways. If I was doing the things everyone else is doing, I wouldn't have the same results.

"I'm still 100 percent invested in helping this team win. I never want to let my teammates down. My lifestyle choices got me to this point. ... Football is more than just what I do. It consumes me."

This is where Brady sounds like Jordan more than ever. They have a lot in common, you know, starting with that assassin's approach to the opposition, whether it's the conference championship or a basement pingpong game between friends. Jordan was investigated by his commissioner, too -- twice, in fact, for high-stakes gambling, before temporarily retiring in 1993 and conceding he might return "if David Stern lets me back in the league." Jordan returned to the Bulls in 1995, retired again, and made the ill-fated final comeback with the Wizards that started five weeks after Brady took over for the injured Bledsoe in the fall of 2001.

A lot of special, modern-day athletes won five rings but couldn't match Jordan's six: Magic Johnson. Kobe Bryant. Tim Duncan. Derek Jeter.

"The great part is the next one for me is No. 6," Brady said, "and I'm not on No. 1. I'm trying to reach No. 6 and I'm on No. 5. If I got to No. 6, that would have great meaning to me. It's not trying to keep up with my idols. It's not Magic, Jeter, Mariano [Rivera], Kobe, Duncan, guys more my age who I always admired. I just want to win because I owe it to my teammates. I'm working this year like I have none, and hopefully it results in a magical season."

At 39, playing a position that requires far less from the body parts (legs) most compromised by age, Brady carried his team like a 39-year-old Jordan could not. If Brady defies the long history of quarterbacks who crumbled after they turned 40, and wins one or two more titles, he can make his case as the tortoise who outran the hare. He can make sure, decades down the road, that Michael Jordan is remembered as the Tom Brady of 2-guards.

The final word on this cross-generational class of titans goes to, of all things, a Prudential financial advisor in the San Francisco area. Kevin Krystofiak, the freshman quarterback at Serra, swung open the door on Brady's career by leaving football to work on his point guard skills. His favorite NBA player, of course, was Jordan. Krystofiak says he believes the Bulls would've won eight consecutive titles had Jordan not retired that first time to take up minor league baseball.

As a student at the University of San Diego, Krystofiak visited Ann Arbor for five or six Michigan games and stayed in Brady's dorm room. They talked late at night about Brady's plans to transfer to Cal or about the girls they'd dated or about the time Krystofiak helped lead the Serra basketball team to the sectional finals. When Brady arrived in New England and started informing his friends he would take Bledsoe's job, Krystofiak tried to keep it real. "We were like, 'Dude, you're a sixth-round pick and Drew is a borderline Hall of Famer. You're out of your mind.' "

But everything is different now, even Brady's mobility. "It's not a grand piano on his back anymore," Krystofiak said. "More like a baby piano."

He laughed. The quarterback who couldn't get on the field for an 0-8 freshman team that scored two touchdowns all season is really going to be the one to fly higher than Michael Jordan?

"I would never say never with Tom," Krystofiak said. "I've said it too many times, even as a friend. I'm sorry, but I'm done saying, 'You're crazy,' when it comes to Tom Brady."