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How Tom Brady’s Future Fits Into the History of Icons Leaving Their Forever Teams

Plenty of legends have played the twilights of their careers in unfamiliar jerseys, from Michael Jordan to Joe Montana to Brett Favre. None of those cases unfolded like Brady’s could, though—and what sets this apart is what could sting so much in New England.

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For all of the highlights of Tom Brady in a Patriots uniform, his final pass as a member of the franchise may have been a pick-six. With New England trailing the Titans late in the fourth quarter of their wild-card-round playoff game on January 4, Brady dropped back to throw just like he had 11,613 times prior over the past 20 seasons. Except this time things didn’t go as planned. The ball bounced off receiver Mohamed Sanu and into the arms of Tennessee cornerback Logan Ryan, who waltzed into the end zone for a touchdown. The score all but ended the Patriots’ comeback attempt, their run of three straight Super Bowl berths, and, possibly, the greatest dynasty the NFL has ever seen.

As fans streamed toward the Gillette Stadium exits, the CBS broadcast cut to a shot of Brady sitting on the sideline, scowling. The most decorated quarterback ever to play the game was left to contemplate how he could engineer another miraculous comeback—or perhaps to consider his impending free agency, as he’s about to hit the open market for the first time in his storied career. “I’m going to tell everybody right now that Tom Brady is coming back to play,” announcer Tony Romo said that night as rain dropped onto the QB’s head. “This is a guess. I think he’s coming back to play. What I saw out of him—not only today, but when I watched him this year—he is not done. He needs help around him. Now, where he’s going to play, is it here or is it somewhere …”

Romo never finished his thought. But since that game, fans, reporters, and talking heads alike have tirelessly tried to fill in the blank. The 42-year-old Brady has made clear in press conferences, Instagram posts, and Hulu commercials that he plans to return for his 21st NFL season. Yet where he’ll play has been the subject of intense speculation. He restructured his contract in August 2019 to void after the league year ends next week, but he’s said little publicly about his mind-set other than that he’s “open-minded about the process.” So will he return to the Patriots, the only franchise he’s ever known? Will he sign with the Raiders, who are moving to a new home in Las Vegas and reportedly willing to offer Brady a two-year, $60 million deal? Will he join the Titans, who ousted him from the playoffs? Or will he push his way to the 49ers, the team he rooted for growing up in Northern California? The list of potential landing spots also includes the Chargers, Colts, and more.

The conversation around these scenarios has played out loudest in New England. Tune in to drive-time Boston sports talk radio and you’re likely to hear callers playing private investigator (did Brady really buy a home in Greenwich, Connecticut?) or amateur GM. Some are angry at head coach Bill Belichick and owner Robert Kraft for letting the Brady standoff get to this point. Others feel that Brady is a product of Belichick’s system whose accolades have been carried by the coach’s genius. Since the Pats’ loss to the Titans, though, seemingly everyone wants to talk about something that once seemed impossible: a Patriots future without Tom Brady. “It’s just all we’ve been thinking about and talking about since that game ended,” says Michael Holley, an NBC Sports Boston analyst who has written three books about the Patriots. “It’s crazy. And there’s a new thought every day.”

If Brady were to move on, he would become the latest legendary athlete to spend the twilight of his career in an unfamiliar uniform. Michael Jordan played for the Wizards. Joe Montana suited up for the Chiefs. Joe Namath was on the Rams, Willie Mays was on the Mets, and Brett Favre did stints with both the Jets and Vikings. There are fewer John Elways, Derek Jeters, and Tim Duncans in sports—all-time greats who retire with the franchise that made them famous—than those who eventually go elsewhere.

But for as much as there’s precedent for Brady’s situation, his stalemate also stands alone. Brady is not playing the will-he-retire game, nor does he have a clear successor on the Patriots. He’s not recovering from a serious injury, and he isn’t being shopped around for future assets. While he’ll turn 43 years old in August, much of the debate surrounding his mediocre 2019 season centered on whether he had declined or the Pats had failed him. There’s never been a football marriage like the one between Brady and New England. And there’s never been a scenario like the one that will determine whether it will continue.

Super Bowl LIII - New England Patriots v Los Angeles Rams
Tom Brady
Al Bello/Getty Images

It’s impossible to overstate what Brady represents to the Patriots fan base. In September 2001, before an entire nation had grown sick of Boston championships, he took over a franchise long defined by losing. From 1971 to 2000, New England went a combined 215-243 with zero Super Bowl wins. After Brady stepped in for an injured Drew Bledsoe, the Patriots went on a Cinderella run to win Super Bowl XXXVI, and they’ve captured five more titles since. Brady has been named league MVP three times and helped to reinvent the modern game.

The onetime sixth-round pick’s career has spanned generations, allowing those who first watched a young Brady lead his team to glory to connect over the Patriots with their children, some of whom have never lived in a world where Brady isn’t a superstar. He’s become an avatar for the many triumphs Boston’s pro sports teams have experienced in the 21st century, supplanting all the greats before him—Larry Bird, Bill Russell, Ted Williams, Bobby Orr—as the region’s preeminent athlete. “When you factor in the success, and the longevity, and where the fan base was before, I’m not sure there’s any single athlete that has come to define a region’s fan base as much as him—anywhere,” says Tom E. Curran, NBC Sports Boston’s Patriots insider, who has followed the team since the mid-1970s.

The Patriots’ dynastic run has made the team a religion in the Northeast, surpassing even the Red Sox for sheer number of devotees. The fans have recited the prayers (“do your job,” “it is what it is”) and learned the tenets that Belichick has preached. Now, they’re reckoning with how one of the coach’s core teachings—never grant any player sacred-cow status—will apply to the greatest quarterback of all time. And because this is New England, people have ratcheted up that debate. “You know how it is up here,” Curran says. “People aren’t happy unless they’re arguing.”

On one side of that argument, Curran says, are the fans who have ridden the Patriots bandwagon for 20 years and “don’t know what the salary cap is, what a slot receiver or an X receiver is.” “Their only opinion is, ‘Don’t let it end—he can’t play someplace else,’” Curran says. “Finances, practicality of how the team will look in 2022, succession plans, they don’t give a fuck.” On the other side are the diehards who obsess over every ramification of the decision. Re-signing Brady—who in 2019 had his lowest passing yardage total since 2010, threw his fewest touchdowns in a full season since 2006, and looked every bit his age for much of the campaign—to a multiyear deal could hamstring the Patriots down the road. It could also deplete the roster in the near term, as the team has several key free agents and limited cap space with which to sign them.

“There’s a sophistication in Boston where people understand what it takes to win championships,” says Dave Brown, a Patriots beat writer for the Concord Monitor who hosts the Entitled Town podcast, which covers the team and local sports media. “Sometimes that means that the players that you’re most attached to emotionally aren’t going to come along for the ride, and that it’s the best path to winning.”

Then there’s the Brady camp’s side of things, and signs have emerged that emotional attachment there may be lacking. Brady and his wife, Gisele Bündchen, put their Brookline mansion on the market in August; in December, Brady stepped down from the Boston charity with which he had worked closely for 16 years. On the field, he often appeared upset with the Pats’ depleted receiving group—and potentially with his offensive line, too. Amid all of that, there were reports that the Chargers and Raiders could pursue him in 2020, and since the calendar turned to the offseason, other potential suitors have entered the mix. The Patriots remain the betting favorites to sign Brady, but a reunion is far from certain. Boston Herald reporter Karen Guregian said in February that the franchise’s chances of re-signing the QB are “not looking good,” and a call between Brady and Belichick last week reportedly wasn’t “particularly productive.” There’s a lot of static, and no one seems to know anything for certain … well, except for maybe Julian Edelman.

For Curran, none of the individual developments have been shocking—he’s written about the potential for a Brady-Patriots divorce since the 2017 season, when a massive rift between the two reportedly occurred. But Curran has been surprised by the recent reaction to his work. When he wrote about the salad days of the Pats dynasty, people enjoyed it, he says. Now that he’s writing what he’s hearing from sources and believes to be true—that Brady will likely land on another team at some point after free agency officially opens next Wednesday—that’s not the case.

“I’ve found people who said they liked my writing, who said they liked me, don’t like me anymore,” Curran says. “And it’s a revelation that if you’re not writing what people want to hear, they’re not going to fucking like you.”

Dolphins v 49ers
Montana with the 49ers
Focus on Sport via Getty Images

Carmen Policy also understands how quickly a fan base can turn when a legendary athlete heads out of town. He, after all, is the man who traded Joe Montana.

Speaking from his Napa County, California, home in early March, the retired 49ers president and general manager says his longtime franchise faced an “almost impossible” decision after learning in 1991 that Montana required surgery for an elbow injury that robbed him of most of the next two seasons. Backup Steve Young filled in and outperformed anyone’s wildest expectations, going 14-2 and winning MVP honors in 1992. With Montana about to turn 37, the obvious move seemed to be for the Niners to transition to the ascendant Young under center.

There was just one problem with that plan: Montana was not only the most popular player in franchise history, but also considered the greatest QB ever at that point. Like Brady, Montana inherited a woebegone franchise that had struggled throughout most of its history and then led it on a run of success the likes of which the NFL hadn’t seen. Four Super Bowls, two MVP awards, and a decade-plus of excellence—Montana’s Niners became the league’s model franchise.

Kansas City Chiefs v Los Angeles Raiders
Montana with the Chiefs
Focus on Sport/Getty Images

“It was Joe who was the leader of the team that brought us out of nothing, out of never having accomplished anything,” Policy says. “We were the kids who were afraid to bring our report card home every single report card period for years and years. And now, all of a sudden, he’s allowing us to walk through the door with the card in our right hand, waving it so our parents can grab and take a look at it immediately.”

In the spring of 1993, the 49ers’ internal strife went public, and after Montana said the team’s decision to name him the “designated starter” came too late, it became clear that San Francisco had to move on. Policy says the Niners seriously considered trades with the Cardinals and the Chiefs, and despite the Cardinals’ offer being superior, the Niners sent Montana to Kansas City because that’s where the QB preferred to play. On April 21, it became official: The three-time Super Bowl MVP and face of football in the ’80s was on his way to Missouri.

The reaction from the 49ers fan base was harsh and swift. “We were trading their god, their icon,” Policy says. The letters that poured into the team facility were so voluminous that they had to be taken to an off-site warehouse for sorting. The Niners’ office came to a virtual standstill, unable to process what had happened. For a brief time, Policy became a pariah in the region he’d helped put on the NFL map. “I had problems going out in some of the restaurants where I’m usually walking in after they lay the red carpet down,” Policy says.

Indianapolis Colts v Tennessee Titans
Peyton Manning with the Colts
Andy Lyons/Getty Images

A similar situation played out in Indianapolis when Peyton Manning left the team with whom he’d become synonymous. The Colts quarterback missed the entire 2011 season after undergoing a series of neck surgeries, and in his absence Indianapolis went 2-14, finishing with the worst record in the league and landing the no. 1 pick in the 2012 draft. That gave the team the opportunity to take Andrew Luck, the most heralded quarterback prospect since Manning in 1998. With Peyton set to turn 36 and reports suggesting that he had likely lost arm strength because of the procedures, the logical move seemed to be moving on from Manning’s $28 million option bonus and starting fresh with Luck.

But according to Bob Kravitz, a former Indianapolis Star writer now with The Athletic, Colts fans wouldn’t hear it. “In that moment they were trying to come up with every way possible, every scenario possible to keep Peyton Manning,” Kravitz says. “They said, ‘Well, you can draft Andrew Luck and make him sit for a year behind Peyton,’ which is about the most absurd thing I’ve ever heard. They said, ‘We’ll keep Peyton and trade Luck for a king’s ransom.’ Letting him go and drafting Andrew Luck was just not something they wanted to deal with on any type of intellectual level.”

San Francisco 49ers at Denver Broncos
Manning with the Broncos
Mark Reis/Colorado Springs Gazette/Tribune News Service via Getty Images

The Colts eventually cut the franchise icon and Super Bowl XLI MVP. (It was a “difficult day of shared pain,” Colts owner Jim Irsay said at the time.) Manning signed with Denver, and during the 2012 season Kravitz saw something strange at Lucas Oil Stadium: Indianapolis fans wearing half-Colts, half-Broncos Manning jerseys. It was a physical manifestation of how the faithful felt, with loyalties split between the Colts and the star who had become inextricably tied with their identity.

“Look, Indianapolis is flyover country,” Kravitz says. “We’re surrounded by Chicago and other big cities, we’re kind of an afterthought and sportswise, they really hadn’t enjoyed any glory since the 1970s ABA Pacers. The Colts were mostly lousy up until they drafted Peyton in ’98. Then he comes in here, he totally embraces the city. He does everything.”

If Brady leaves New England, the effect will approximate what Bay Area and Indianapolis fans experienced. But there are several key differences, and chief among them is Brady’s leverage. Neither Montana nor Manning left of his own volition, as it appears that Brady might do next week. Most all-time greats who changed cities late in their careers were dumped by their respective teams; in this case, it seems that Brady would be the one doing the dumping. And that crucial distinction is fueling a sense of unease and anxiety in New England.

Green Bay Packers vs Seattle Seahawks - November 27, 2006
Brett Favre with the Packers
Kevin Casey/NFLPhotoLibrary

While the annals of sports history are littered with examples of famous athletes playing out the string in new locales, no situation compares to the one currently involving Brady. Montana and Manning were pushed out because of injuries and promising young options waiting in the wings. Joe Namath was waived by the Jets in 1977 and signed with the Rams for one forgettable season. A broken-down Johnny Unitas started just four games for the Chargers after being traded to San Diego in 1973. Willie Mays was shipped to the Mets during his age-41 season because the San Francisco Giants were losing money. Given his GOAT status, Michael Jordan’s move to the Wizards in 2001 may seem the most germane to the Brady discussion, but even that doesn’t compare. Jordan had been retired for three full years before signing in Washington; Bulls fans had likely already mourned his departure. There are few, if any, examples in North American sports of a legendary athlete reaching free agency at this stage and walking away when re-signing was in the team’s best interest.

The closest comparison to Brady’s case may be the Brett Favre saga from 2008, but even that scenario wasn’t especially similar. After years of toying with retirement, Favre decided to hang up his cleats—or so we thought—at age 38. He made an official announcement in March fresh off a season in which he had contended for league MVP and led his team to the NFC title game. Yet as the Packers began their transition to Aaron Rodgers, whom they had selected in the first round of the 2005 draft, Favre voiced a desire to play again. Suddenly, the front office faced a difficult decision: Would it continue with Rodgers? Or would it reunite with Favre, who still had something left in the tank?

Football - NFL - Jets vs. Titans
Favre with the Jets
Anthony Causi/Icon SMI/Icon Sport Media via Getty Images

According to Tom Silverstein, who covers the team for the Milwaukee Journal Sentinel, the Packers would have been amenable to benching Rodgers for another season and paving the way for Favre to come back. But by 2008 there was a sense of “retirement fatigue” in the franchise—that it could no longer be subject to the quarterback’s whims, even if Favre had the support of the fan base. Green Bay traded him to the Jets in August and handed the keys to his immensely talented successor. “This was all fueled by Favre,” Silverstein says. “This was his decision to retire.”

The Patriots, of course, also had a succession plan in place for Brady. He simply outplayed it. New England picked Jimmy Garoppolo in the second round of the 2014 draft, when Brady was 36. That fall, after a Monday-night loss to the Chiefs dropped the team to 2-2, there was speculation that the Pats dynasty was dead. But Brady and New England roared back, winning Super Bowl XLIX and then Super Bowl LI two years later. In 2017, Brady told ESPN he planned to play until he was 45, and that October New England shipped Garoppolo to San Francisco for a future second-rounder. Brady was named MVP that season, reached the Super Bowl in February, and won another title the next season. But the compound effect has been obvious: The only other quarterback on the Patriots’ 2019 roster was fourth-round pick Jarrett Stidham.

Unless Jordan Palmer is right about Stidham, or unless Belichick wants to see whether he can win with Andy Dalton, New England now appears to have no blueprint for life after Brady. A franchise that’s achieved much of its success by planning for and adapting to any eventuality could be facing uncharted territory. Belichick has always believed it’s better to let star players walk a year early rather than a year late. The question with Brady is whether that time is now.

“There is no quarterback who’s played a full season after this age, and he’s coveted not only by the team he’s been playing for, for the last 20 years, but also by other teams,” says Brown of the Concord Monitor. “His team is in a position that no one has ever been in before except maybe the Packers, but they had a clear successor. The Patriots’ best option is 43-year-old Tom Brady. They don’t know if they can work out a deal that makes sense for any 43-year-old player. I think that’s why this one is different.”

AFC Wild Card: Tennesee Titans Vs. New England Patriots At Gillette Stadium
Brady with fans after a game
Stan Grossfeld/The Boston Globe via Getty Images

The first time Policy saw Montana wearing a Chiefs jersey, he could hardly believe his eyes. “You see this guy, and he’s always dressed in a Brioni suit with the best of Italian shoes and a good-looking shirt,” he says. “And then he comes walking in wearing jeans, an untucked shirt, and tennis shoes. This doesn’t look right. Is that him?” The feeling was similar in Indianapolis when pictures surfaced of Manning in a Broncos uniform—“really, really odd,” Kravitz says—and it was amplified in Green Bay when Packers fans watched Favre play two seasons in Vikings purple. “There was just a large contingent of fans who disowned him,” Silverstein says. “[They] wanted nothing to do with him and felt he was a traitor.”

The sight of Brady in another uniform would be no less jarring for Pats fans, but Brown believes the quarterback would avoid the brunt of their anger. Let’s say that Brady signs with a dark-horse team like the Tampa Bay Buccaneers. And let’s say that the Brady-led Bucs go on to make the conference title game while the Pats miss the playoffs. Brown thinks the New England fan base would be apoplectic, turning their ire toward the organization for letting Brady walk. He says that a faction of fans is still upset over the 2016 Chandler Jones trade even though the Patriots’ past two championships stem largely from it. And there’s an even more vocal contingent that points to the Niners’ Super Bowl LIV appearance as proof that Belichick should’ve held on to Garoppolo.

“Take what happened with Jimmy out in San Francisco, and then apply it,” Brown says. “It’s going to be the same overreaction to what Jimmy did with all of the anger focused on the Pats, but it’s going to be magnified to Tom Brady proportions.”

The Niners, Packers, and Colts all dealt with this anger to varying degrees. Montana made the AFC championship game in his debut season with the Chiefs. Favre’s Jets season was a bust, but then he retired and unretired again and led the Vikings to the NFC title game. After joining the Broncos, Manning orchestrated one of the greatest quarterback seasons ever and made two Super Bowls, winning one. These moments are as much a part of those players’ legacies as anything they did on the franchises with which we most closely associate them.

If negotiations stall, the Pats sputter, and Brady finds success elsewhere, things in New England will get ugly. “A lot of knives are sharpened for Bill Belichick that remain in people’s socks and will quickly be unsheathed if the Patriots don’t do better than Tom Brady does wherever Tom Brady goes,” Curran says. The only cure would be winning. In Green Bay, Silverstein says, mostly all was forgiven after the Packers won Super Bowl XLV in February 2011—coincidentally, just after Favre retired for the third and final time. There’s a parallel in San Francisco, Policy says: The Niners won Super Bowl XXIX behind Young in 1995, and three months later the city held a retirement ceremony for Montana in its financial district. “In [the fans’] minds, they said, ‘OK, we’ve got a pretty darn good organization running this franchise and we’re in good hands, and now it’s a new era,’” Policy said. “They respected Steve and admired him.”

Endings are rarely clean, but the most successful marriage in football history seemed destined to end with something better than a premature playoff loss to Tennessee. For a fan base that worries about things reverting to how they were before 2001, accepting that this relationship might really be over is the hardest part. The identity of the Patriots franchise—and in many ways, the identity of the region—has changed dramatically over the past 20 years, with Brady as a driving force. The next few days will reveal whether that identity will remain intact or a new era will begin.

“Every day in Boston is like a referendum on whether the four teams can win a championship,” Brown says. “That’s where everyone’s head is going to be with the Patriots if Tom moves on: What’s the chance of us winning a championship in 2020?

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