Sports

Can Jonathan Kraft Keep the Patriots’ Reign Alive?

Robert Kraft is the charming, free-spirited Patriots frontman whom players, coaches, and fans adore, while son Jonathan is the brainy, reclusive family enforcer. But as the Brady-Belichick era slowly draws to a close, could Jonathan be just the Kraft we need?


robert kraft jonathan kraft

Photos by Benjamen Purvis/AP Images

On a cold evening this past January in Kansas City, Robert Kraft watched the Patriots vie for a spot in Super Bowl LIII much in the way he has spent nearly every NFL Sunday for the past 25 years: seated in a luxury owner’s box next to his eldest son and heir apparent, Jonathan. As Pats running back Sony Michel made a short burst up the middle to cap off an 80-yard drive for the first touchdown of the night, father and son stood and cheered in unison. High above the stadium of fans, Robert and Jonathan couldn’t have cut more different figures.

Robert, 78, who has acquired a taste for designer duds of late, wore a hot-pink tie with a black half-zip sweater, black slacks, and black sneakers. The dark attire only served to accentuate the flowing white hair that tufted over his ears in the style of an aging rock star. Beside him, Jonathan—55, half bald, and bespectacled in a standard-issue navy suit that draped over his lean, greyhound frame—could easily have been mistaken for his accountant. Jonathan clapped, then gave a little fist pump, which is just about all anyone sees or hears these days from the intensely private scion. He’s cut back on his radio appearances and rarely, if ever, gives on-the-record interviews to journalists, myself included.

When Jonathan does appear on screen, he often seems to blend into the background, practically invisible. Later that same day, after the Patriots beat the Kansas City Chiefs for the AFC title, CBS commentator Jim Nantz and former Patriot Vince Wilfork lined up in front of the camera beside both Kraft men. A gushing Wilfork handed the Lamar Hunt trophy to Robert, calling him “my man.” Robert said a few words before Nantz took the trophy back, swiveled it right past Jonathan as if he were the least consequential man alive, and handed it to coach Bill Belichick and then to quarterback Tom Brady while Jonathan shuffled out of the way and eventually disappeared from view.

That night, while coaches and players popped bottles of champagne in the locker room after securing their shot at an unheard-of sixth Super Bowl championship in just two decades, none of them could have imagined that what had transpired over the past 48 hours was about to plunge their beloved patriarch into a humiliating and career-endangering scandal. The day before and more than 1,300 miles away in Florida, Robert had appeared on a different kind of screen, a dimly lit video feed, to an audience of just a few police officers who watched from a remote viewing room as the billionaire allegedly received sexual services at the Orchids of Asia day spa. They watched as he handed over multiple bills and hugged the women who had given him a massage before stepping out of the spa and into a Bentley that was waiting to whisk him away. He returned the very next day for a final visit before boarding a jet, flying to Kansas City, and joining his unsuspecting son in the luxury box.

The significance of those two days before the AFC title game, and of that grainy police video, became clear about a month later when Florida prosecutors accused Robert and 24 other men of soliciting prostitution. The allegations—splashed across hundreds of newspapers and news sites—became a national scandal within minutes, turning Robert into an overnight punch line. A wave of resignations among the suspected high-profile johns soon followed. Meanwhile, the question bubbling up in Boston was whether the scandal might mean the premature end of Robert’s run as king and the subsequent ascension of Jonathan to his father’s throne. At the Patriots’ opening game this month in Foxboro, would Robert even be in the owner’s box? Or, for the first time in memory, would Jonathan look down on the field alone?

In reality, family insiders say, the transfer of power has actually been long under way. The massage-parlor scandal, and Robert’s willingness to take that kind of risk, served less as a revelation and more as a reminder that Robert was not the only leader in Foxboro and that Jonathan’s prominence and stature in the family business have been growing steadily. “Jonathan’s responsibilities have increased very significantly,” says Marc Ganis, an NFL business consultant who knows the Krafts well. “There have been some changes because Jonathan is now as much of a visionary as Robert is.”

Part of the shift can be traced back to the death of the Kraft matriarch and moral compass, Myra, in 2011, an event that nearly shattered the soulful Robert and raised for the first time the question of how long he would remain in charge. Indeed, observers of the Kraft family talk about two epochs of Robert’s life: with Myra and after Myra. In both modes, Robert has been an extrovert drawn like a moth to the spotlight. But while he was married, he managed to project a personal image that, for the most part, was sober and reserved. Since 2011, though, he’s been acting more like a ’90s record-company impresario than a family man who made his fortune in the paper business. At nearly 80, he’s transformed into a jet-setting, Nike Air Force 1–wearing, floppy-haired playboy. For six years he dated Ricki Noel Lander, a model in her thirties, after meeting her at a glitzy L.A. party. In July he stepped out with a new woman, 45-year-old New York doctor Dana Blumberg. He’s been photographed sharing bottle service with Beyoncé and Jay-Z. In 2016, he rekindled his friendship with Donald Trump and has been seen at the president’s side several times since. Well before Massagegate, there was a sense among Kraft watchers that Robert’s third-act Rumspringa had lured him away from his senses and the team. In turn, insiders say, Jonathan has stepped in to fill the void.

In contrast to his father’s gregarious personality, Jonathan’s quiet, work-behind-the-scenes habits mean that Pats fans and outsiders generally see him as either a silent sentry standing by Robert’s side or as his loyal and fierce enforcer taking public shots at the team’s litany of sometime enemies, including the NFL, the media, and league rivals. As a result, many New Englanders have developed a skewed picture of Jonathan and view the prospect of his future reign with equal parts suspicion and dread. “The Jonathan I know is a whip-smart, passionate guy who has a good heart and who can also throw some haymakers,” says Tom Curran, a longtime Patriots beat reporter. “But the caricature is that he might be a tyrant prince.”

No one knows what Robert’s fate will be with the NFL as a result of the massage-parlor scandal, nor when he plans to step down. But one thing is certain: When Jonathan does finally take over, he will forever change the relationship between owner and team, and owner and fans. Not because he is a dilettante or a tyrant, neither of which is true, but simply because he isn’t Robert.

Jonathan on the field with his dad, Robert. / Photo by Icon Sportswire/Getty Images

In 1992, when the Patriots were the laughingstock of the NFL, Robert and Jonathan paid a visit to the team. The Pats’ record was 0–9. The inflatable bubble where they practiced smelled like manure. “There used to be a horse track down there,” says former quarterback Scott Zolak. “The stadium was a shithole.” At the invitation of the team’s general manager, the Kraft men ambled onto the field and Zolak left a huddle to meet them. At the time, Zolak recalls, Robert had brown hair and a chubby face, while Jonathan, then 28, was his father’s taller, slimmer, and quieter sidekick. They both shook Zolak’s hand. “I thought, ‘Who the hell are these guys?’” Zolak says. “You didn’t know who Robert was back then.” But the Krafts already had a sense of where they were going. Zolak remembers Robert telling him, “I’m going to own this football team one day.”

It might have sounded awfully ambitious, but to comprehend why it was even conceivable—and to understand who Jonathan really is—you have to know something about his father’s spectacular and improbable ascent. Robert grew up lower-middle-class in Brookline, the son of small-business owners who were active in their synagogue. In the early 1960s, Robert met Myra Hiatt, whose family ran in a tonier circle of Boston’s Jewish community and whose father ran a profitable, but not world-beating, packaging company. Robert asked her out and, as he’s told it, Myra popped the question to him on their very first date. After they married, Robert took over his father-in-law’s Worcester business and, through a series of shrewd and risky investments, grew the company into a vast multinational. Robert and Myra soon started donating money to schools and hospitals all over town, moved into a Chestnut Hill mansion, and in 1964 welcomed their first child. They named him Jonathan. Blessed with the combination of his mother’s generous spirit and his father’s ambition and business acumen, “he got the best from both his parents,” Ganis says.

Next came Daniel. Now president of the Kraft Group’s international operations and a subordinate to Jonathan, he is known as the most down-to-earth of Myra and Robert’s four sons. One source told me, with evident affection, that Daniel was the Kraft man you’d be most likely to mistake for a UPS driver. The Kraft’s third boy, Josh, president and CEO of the Boys & Girls Clubs of Boston and president of the New England Patriots Foundation, is the most like Myra, the philanthropist. “He is a kind soul,” says Mike Reiss, who worked for the Patriots in the 1990s and has covered the team as a journalist ever since. David, the youngest son and a one-time Kraft Group executive, is the rebel child who left the family business in 2012 and sued his father over access to the family’s trust.

Contrary to the stereotype of business titans of his generation, Robert was a present, engaged, and caring father. “I don’t ever remember my father, [when I was] a young boy, missing a birthday, missing a game, or not being home for dinner at 6 o’clock at night,” Jonathan once told the Harvard Crimson. He was supportive of his sons but not overbearing, and has said that he wanted the Kraft Group to remain in the family only if his children were eager to take the mantle. When Jonathan, who has always revered his father, showed an early interest in business, Robert patiently nurtured it.

To start, Robert put a teenage Jonathan to work in his Leominster paper factory, where his son could learn the family business from the ground up. But it was only after Jonathan earned degrees at Williams College and Harvard Business School and sharpened his skills at Bain & Company for two years that Robert welcomed his chosen son into his company’s executive suite. Brainy, ambitious, and armed with a singular understanding of the boss, Jonathan was a formidable addition to the family business. “From the early days, they fit together like a hand in a glove,” says Brian O’Donovan, the former general manager of Foxboro Stadium. “They were like one person.”

For the most part, people who have worked closely with the Krafts describe a virtual mind meld. But, like the two hemispheres of a brain, father and son have different proclivities and strengths. “Jonathan is very calculated in terms of how he views the world,” says Stephen Jones, the heir to Dallas Cowboys owner Jerry Jones and a senior executive with the team. “Bob is probably a little more prone to using his people skills and his relationships, where Jonathan’s going to use his pencil and his mind.”

Throughout the 1990s, they each helped the family business and the Patriots—which they bought, as promised, in 1994—according to their strengths. Robert, acting on instinct, hired a curmudgeonly coach with a losing record named Bill Belichick—and won the coach’s trust. Jonathan, meanwhile, set about revitalizing the black sheep of Boston sports franchises, negotiating a complex financing deal for a new stadium and transforming the team’s website into a state-of-the-art digital-media operation at a time when the Internet was just coming into existence. But even as father and son specialized, they didn’t separate. To this day they work in adjacent offices, frequently calling out to each other for counsel.

Meanwhile, Jonathan followed in Robert’s footsteps at home, creating his own tight-knit family. At Bain, he met Patti Lipoma, a star consultant and football-loving Texan, who went on to Harvard Law and now runs a home-goods store in Newton. They married at Robert and Myra’s home in 1995 and have three children. Like Robert, Jonathan has been a devoted and engaged parent, always leaping at the opportunity to coach youth sports and hardly ever missing an afterschool game or concert. Although he tends to work around the clock (friends and business associates alike report that he responds to emails seemingly instantly at all hours), “he always takes time to be at his family’s events,” Ganis says.

As Super Bowl trophies began to accumulate in the 2000s, Jonathan took on even more responsibility within the Kraft Group, overseeing the paper and packaging business (along with brother Daniel), the New England Revolution, the Krafts’ convention and events business, and Patriot Place, the vast commercial real estate development that sprang up around Gillette Stadium. He also made a name for himself in Boston’s tech scene, doling out millions in early-stage investments and whispering advice into the ears of the city’s entrepreneurial elite. “He’s one of the few people I met in the course of reporting on the NFL,” says Mark Leibovich, a New York Times Magazine journalist who wrote a book about the league, “who you think could just step in and be the CEO of some Silicon Valley company.”

The picture that emerges is not of a typical patriarch and successor, but rather of two coequal partners with complementary skills. The Krafts’ working relationship is not unusual, says Gerard Donnellan, a psychologist in Lexington who advises family businesses. Historically, in family-run businesses, there would be two partners, he says. “One was the inside guy and one was the outside guy. The outside guy goes to lunch, he’s known, he’s the face of the business. The inside guy crunches numbers, does the books, and worries about getting product out the door.” The two partners work as a unit, collaboratively and without hierarchy, each one indispensable to the other.

Or, as another source said of Robert and Jonathan, somewhat more colorfully: “They are a two-headed monster.”

Jonathan taking in the sights at Super Bowl LIII. / Photo by Simon Bruty/Getty Images

In March, the NFL’s billionaire owners and their extensive coteries descended upon Arizona for the annual league meeting. A procession of black SUVs and limousines delivered them to the Arizona Biltmore, their oasis home for the next three days. As the owners entered the five-star hotel, a sprawling ochre palace surrounded by emerald-green lawns improbably sprouting from the desert ground, it was a comfortable 78 degrees. The skies were clear. And the press was waiting. But they didn’t spot the owner of the league’s winningest team. Robert Kraft managed to check in and get to his room without even making a pass through the lobby.

It was an odd backstage entrance for the man who, year after year, has been the star of the show. “He holds court,” says Jarrett Bell, an NFL reporter for USA Today. “You know how he is, affable, quotable—he’ll talk about a variety of subjects.” But this year was different. The meeting came almost a month to the day after Robert was named in the massage-parlor scandal. The Patriots’ longtime PR man, Stacey James, had already warned journalists covering the event to keep their expectations low: Robert would not be talkative this year.

Jonathan always attends the retreat with his father and typically spends his days flitting from meeting to meeting, a tightly wound bundle of energy. “He is constantly busy,” Ganis says. “He comes out of owners’ meetings and invariably he has his phone to his ear. I don’t mean once or twice. I mean all the time. He is on the phone exiting the meeting room and going into the bathroom.”

This year, however, Jonathan had to assume his other long-standing role in the Krafts’ partnership—his father’s defender. When Tom Curran approached Robert in the hotel lobby and asked how he was doing, Jonathan leapt to action, pulling Curran aside and objecting to his television coverage of the scandal. “That’s Jonathan,” Curran says. “He’s going to defend his dad to the nth degree. If someone attacks his dad, he’s going to attack that person.”

Jonathan first showed his willingness to protect—and try to please—his father when the Krafts attempted to build a football stadium in South Boston. Almost from the start, the campaign was a calamity. Southie residents revolted against the project, and as momentum turned against Robert, he made comments that came off as a threat to move the team out of state. House Speaker Tom Finneran called Robert a “whining multimillionaire” and the press lampooned him. As Robert weathered attacks, Jonathan came forward as the family’s public face—and defender. But despite his best efforts, Jonathan did little to smooth things over. In his public remarks, Jonathan came off as someone unwilling to acknowledge any responsibility for the fury directed at him and his father. “I don’t know if it’s anti-Semitism, or anti-Kraftism, or anti-footballism, but it’s really strange,” he told a Globe reporter who wrote that tears welled in his eyes as he spoke. “If they knew my father and what he has accomplished—I mean he is a great man.” At other times, Jonathan came off as entitled: “From our perspective,” he said, “if you’re going to spend hundreds of millions of dollars of your own money, you’d think they’d cut you a little slack.”

When reporters went to see Jonathan in December 1998, after the project had failed, they found a scene that revealed a lot about what drives him. In the basement of a downtown Boston office, the Krafts had spent more than $1 million building a full-scale model of a luxury box like the ones they had planned to sell in the South Boston stadium. The model had a bar, plush leather chairs, mahogany floors, a patio with stadium seats, and a detailed mural simulating a view of the field. Standing in this little monument to Robert’s doomed vision, Jonathan, then 34, was dejected. “I’m personally disappointed because I really wanted this to happen for my dad,” he said. “I feel like I failed and I didn’t get it done.”

Jonathan reprised his role during the Spygate cheating scandal and again during Deflategate. It was Jonathan, for instance, who shaped the Patriots’ combative stance during Deflategate as the family tried to clear the good names of Tom Brady and the team. He was the face of the organization’s scorched-earth defense, publicly ridiculing coaches and other personnel employed by the teams that initially made a fuss about Brady’s allegedly underinflated footballs. He accused the NFL of maliciously leaking information about the ensuing investigation to reporters. He also gave approval to the Patriots’ communications staff to launch a website attacking the results of the NFL’s investigation.

Three years later, Jonathan was forced to confront the next crucible: his father’s massage-parlor scandal. According to a source familiar with the situation, Jonathan helped Robert write his first significant statement on the issue, honing a message that was at once contrite, defiant, and designed to jump-start his father’s redemption.

It’s a noble pursuit to protect your kin. But it can also turn absurd. Consider Jonathan’s life leading up to 2019: For three decades, he has gone to the mat to defend his father’s legacy, dignity, and good sense even though, in doing so, he has sacrificed his own public standing. He maintained Robert failed in Southie because the powers that be had it in for him. He argued Deflategate was a witch hunt. If that’s not enough, he’s running a multibillion-dollar conglomerate—for which his father gets all the credit—while Dad’s at a Florida strip mall on a police surveillance tape allegedly getting a happy ending. And now—you guessed it—Jonathan has to defend him over that, too.

On April 14, nearly four months after visiting the Florida day spa, Robert made a rare public appearance courtside at TD Garden to watch the Celtics’ first game of the playoffs. In the third quarter, his face appeared on the JumboTron—and the crowd lost it. Twenty thousand Bostonians leapt to their feet, screaming, whooping, and cheering for a full-throated 15 seconds. Robert drank it in, pumping his fist, clapping along with the crowd, and beaming.

While Jonathan can seem inscrutable in public, Robert is the least mysterious man in the world. Gregarious, glad-handing, and affectionate, he wears everything on his sleeve. He lets friends, fans, and strangers in. He has unashamedly wept, orated, bear-hugged, and basked in the adoring applause of a million demented Boston sports fans. Robert’s inner life is his outer life, and we have all been witness to it. “Robert has that David Ortiz effect,” Zolak says. “He lights up the room. He makes everybody feel important.”

Many former Patriots have a cherished story about receiving special treatment from Robert, and they love him for it. “The players look at Robert like a second dad,” says Dane Fletcher, a former Pats linebacker. “A guy you live and die for.” The devotion Robert inspires in his players also pays dividends, conferring on the Patriots a competitive advantage unique in the NFL. Fletcher, who played his first NFL seasons with the Pats, returned to New England later in his career even though, he says, another team had offered him more money. The reason? He wanted to play for Robert. When I asked if other players had also accepted pay cuts to play for Robert, he said, “Absolutely.”

Although Jonathan has inspired loyalty and admiration among many close associates, he also has earned a reputation, in some circles, for being more distant and severe than his father. “Jonathan’s a little closer to the chest, a little more serious,” says a former Patriots player. He’s also known to have more of a temper. “He definitely runs pretty hot,” says another former Patriot. In interactions with subordinates, he doesn’t hesitate to remind them who’s boss. Zolak, now a Patriots analyst and host on 98.5 The Sports Hub, recalls Jonathan putting him in his place after a screwup. Once, on his show, Zolak ridiculed a commercial aired by Budweiser, which happens to be the beer sponsor of Gillette Stadium. Budweiser complained, Zolak says, and, a few days later, Jonathan, who is around 5-foot-9, approached the former QB, who is 6-foot-5. Jonathan reached up, clapped Zolak on the cheek, and said, “Hey, sweetie, you know better than that.” Zolak was intimidated. Point made. It won’t happen again, he remembers thinking. “Jonathan won’t have a problem telling you if something’s wrong. He’s pretty demanding,” says Zolak, who likes Jonathan but acknowledges that he is a “get-in-your-face” kind of guy.

The differences between father and son are not lost on Jonathan. When asked during a television interview what it’s been like to work side by side with his dad, Jonathan launched into a reverie about why his father is such a great businessman. “He knows how to make people feel really good…to feel a connection to you beyond a paycheck,” he said. “He has a gift.” It’s hard not to notice in Jonathan’s praise an awareness of his own limitations and a recognition that competence, even brilliance, alone does not bring loyalty or love.

As a result, Robert’s and Jonathan’s contrasting styles have led to different relationships with some key Patriots employees, including Belichick. For 20 years, Robert has skillfully managed his relationship with the prickly man he brought to Foxboro, letting the occasional slight roll off his back and studiously staying out of Belichick’s way. But Jonathan, at times, has had a more confrontational relationship with the coach. Part of this stems from Jonathan’s role managing the business of the Patriots, which can conflict with the imperatives of the football team. Scott Pioli, formerly Belichick’s right-hand man in personnel matters, stresses that Jonathan was always patient and respectful in disagreements with him and Belichick. But he also says that Jonathan was “passionate,” a word people frequently use to describe how he advocates for his ideas. “Jonathan has a strong voice,” Pioli says, “and he could disagree strongly.”

Although Pioli now admires Jonathan and has affection for him, Belichick’s relationship with the boss’s son remains more strained, according to five sources with knowledge of internal Patriots dynamics. NFL insiders believe that Belichick doesn’t have a lot of respect for Jonathan and that the coach and his key staff members would not want to work for him. (Belichick, through a Patriots spokesperson, says the notion that he doesn’t respect Jonathan is “completely false.”) Still, people close to the team say that tensions have only gotten worse in recent years. “Especially since Myra’s passing, the more power Jonathan has had, the more Robert is on the West Coast and jet-setting around, the more Jonathan’s presence has become polarizing,” says one veteran NFL reporter. “This isn’t a well-kept secret. People go to [league events] and they talk. They say to their friends, ‘The day the old man is out of here, I’m out of here.’”

Jonathan Kraft speaks to the media in front of the team’s customized Boeing 767. / Photo by The Boston Globe/Getty Images

When Jonathan finally does get the chance to lead without his father by his side, he will have his work cut out for him. After all, the Pats seem on the brink of falling apart. On the 2019 season’s opening day, Brady will be 42 and Belichick will be 67. Meanwhile, Robert’s prostitution scandal has overshadowed what would otherwise be regarded as a five-alarm crisis in Patriots Nation. Key members of Belichick’s staff spent the off-season running for the exits in what the Globe dubbed “an unprecedented wave of departures.” As the team geared up for the new season, the Patriots lost their linebackers coach, character coach, wide receivers coach, cornerbacks coach, assistant quarterbacks coach, defensive line coach, and their brand-new defensive coordinator, who left after only a month. To top it off, director of player personnel Nick Caserio (a top Belichick lieutenant) tried to leave as well, before the Krafts invoked a clause in his contract and blocked the move.

Taken together, the thinning staff and the aging stars mean that Jonathan will preside over a team that bears virtually no resemblance to the ones that won six championships. He also stands to inherit a fan base that, partially through his own reluctance to join in the spotlight, has become something like a cult of personality to his father. At every Super Bowl victory parade, including the one on a frigid Tuesday last February, thousands of bundled-up fans hang on every one of Robert’s shouts and fist pumps. It’s hard to imagine Jonathan thrilling the crowds in the same way. After all, they don’t teach charisma at Bain and you don’t learn crazy at HBS.

Instead, Jonathan has pursued an inexplicable and catastrophic PR strategy, seemingly designed to ensure that his sharper edges are on full display while his most attractive qualities remain hidden from public view. He does not, for instance, tout his extensive philanthropy, which, more often than not, involves bringing his business skills to bear on good works. At Williams College, he helped oversee the investment of the school’s endowment. At Massachusetts General Hospital, the board of trustees recently elected him as chairman. At Boston Children’s, he has essentially served as a management consultant to the hospital’s pioneering stem-cell-research lab, drawing up a long-term plan to guide the lab’s hiring and equipment acquisitions. “In the academic world,” says Leonard Zon, the lab’s director, “this never happens.”

Even farther from public view, Jonathan has a habit of carrying out random acts of kindness. Pioli recalls that once, after he’d stopped working for the Patriots, Jonathan called and asked if his family would like tickets to see Taylor Swift at Gillette Stadium. Years later, he’d still remembered that Pioli’s young daughter was a fan. “This call came out of nowhere,” Pioli says. “Jonathan didn’t have anything to gain.” Behind the scenes, Jonathan has also made a quiet habit of helping strangers, from lining up much-needed college tuition aid to, in one case, arranging life-saving medical treatment at MGH for a woman who couldn’t afford it. “He doesn’t want recognition,” says a person familiar with Jonathan’s thinking who would only speak anonymously, citing Jonathan’s decision not to participate in this story. Whether it’s good works or business feats, this person says, “he never wants people to know.”

Some of this is surely due to Jonathan’s private nature. But it also true that for the past three decades he has strenuously avoided upstaging the father he still reveres. “He’s never going to try to step in front of his dad in any shape or form,” says Dean Spanos, the owner of the Los Angeles Chargers and a friend of the Krafts. “He’s letting his dad enjoy it.”

But at what cost? It’s possible to wonder whether Jonathan’s public abrasiveness reflects some level of resentment—if, after choosing to live in his father’s shadow, he has come to bristle at the inevitable consequences of that choice. As if he realizes that his fierce loyalty to his father has meant never receiving the praise he deserves. Curran thinks he’s seen something like that in Jonathan: “He’s not going to publicize [his achievements] on the radio and he’s not going to say it to you for an article, but still, he’s very much aware of ‘These are the things I’ve done and haven’t been credited for and nobody even likes me.’”

Viewing Jonathan’s circumstances in the most sympathetic light, it’s possible to perceive a kind of tragedy. By all accounts, he is a brilliant business tactician who, if he had set out on his own, almost surely would have succeeded, perhaps fabulously. Instead, though, he enlisted in the family business, choosing to become the silent, unloved operator who has helped his father achieve glory and adoration. And what thanks does Jonathan get? Well, the pay isn’t bad, but he also gets ridiculed, he gets misunderstood, and he gets reminded every day of who he is not. Jonathan may not have the magic touch that kept Belichick, Brady, and a million crazy fans in the Patriots’ corner, but Robert, as good as his instincts may be, arguably caught some lucky breaks, too. He benefited from a previously unsuccessful head coach who magically turned into a legendary inspiration for curmudgeons everywhere, and a sixth-round, second-string QB who only became a starter when Drew Bledsoe got hurt, then treated his body like a temple and somehow kept his impossible physique long after, in any rational world, his warranty should have expired. Those certainly aren’t things you can count on when writing a long-range business plan.

The inevitable work ahead when Brady and Belichick retire—the rebuilding of a once freakishly successful team—will be far harder than anything that has come before. It may call for smarts more than serendipity. It may call for someone more accustomed to putting their nose to the grindstone than someone who has a talent for making people happy. And maybe, just maybe, Jonathan will bring exactly what the times demand: fundamentals, discipline, and sound economics; less glitter and glamour, less eccentricity; and more stay-within-the-lines, strategic enterprise-building. It’s possible that we might never love him, but he might be just the Kraft we need.