He Can’t Lose

How sports agent Bob LaMonte ’68 wins—no matter who comes out on top in Super Bowl 50

It’s been a busy winter for Bob LaMonte ’68, NFL agent extraordinaire. After recent hires by the New York Giants and the Philadelphia Eagles, LaMonte again represents nearly a quarter of all head coaches in the National Football League, not to mention dozens of football executives and coordinators.

But like in most years, LaMonte is taking a break from the flurry of winter contracts to attend the Super Bowl, by his count his 17th time seeing the game in person, although even he has a hard time justifying the price.

Super agent or not, LaMonte is a former high school history teacher who grew up sneaking into Kezar Stadium to watch Niners games he couldn’t afford—and who still blanches at $80 parking. “Bring money,” he says to anyone braving the event for the first time. “It’s a Circus Maximus. It’s become absolutely absurd.”


At least this year LaMonte can’t lose. He has one client with the Carolina Panthers, defensive coordinator Sean McDermott, and another with the Denver Broncos, Tom Heckert, director of player personnel.

The Super Bowl is a far more intense experience when he has a head coach in the game. That happened most recently with John Fox, who led the Broncos to the Super Bowl two years ago, when they were routed by the Seattle Seahawks. “If he wins, it’s phenomenal,” LaMonte says. “It’s like heaven on earth. If he loses, it’s hell. Because it’s all on him. His anguish is your anguish.”

Indeed, the old Santa Clara nose tackle says losing the Super Bowl is so devastating, it’s almost better not to make it at all than lose. No matter how close you get, there’s just one genius head coach at the end of the game—and 31 idiots.


Certainly LaMonte got an early education in just how elusive victory can be. In the early ’90s, before he began to focus exclusively on coaches and management, LaMonte represented players on the Buffalo Bills, the only team to go to four Super Bowls in a row, cruelly wining none of them.

While even the losing team has a party—they’re huge events planned long before the outcome—the end of the Bills’ run was so painful that it made any kind of celebrating difficult. “At the fourth one, there was no one there but the band playing,” LaMonte says.

LaMonte, though, has been on the winning side of the equation more than once. And he has no hesitation when it comes to naming his favorite Super Bowl moment: the Green Bay Packers’ win in Super Bowl XXXI under head coach Mike Holmgren, his longtime friend dating back to when both were high school coaches in San Jose.

“It’s like your first love,” LaMonte says. “Nothing will ever take the place of that game. It’s one of the top five moments of my life.”


LaMonte chanced into being a part-time agent in the early ’80s when a former student tapped him as his representative after a stellar collegiate career. But it was Holmgren’s ascent as an NFL coach that really paved the way for LaMonte, his agent, to carve his niche as the league’s preeminent representative of coaches.

After the Packers’ victory, LaMonte remembers the two of them sitting in the back of a limo sipping champagne as they cruised through New Orleans, pondering whether it was any better than the beers they shared after high school championships. Answer: Yes, but both are amazing.

The second-sweetest Super Bowl moment came in 2003 when Jon Gruden, now an ESPN broadcaster, coached the Tampa Bay Buccaneers to a resounding victory over the Oakland Raiders, the team he had acrimoniously left less than a year earlier.

Gruden’s exit from Oaktown marked the rare occasion that LaMonte aired his business publicly, forcing the coach’s release by telling the press that there was a “zero percent” chance Gruden would stay in Oakland past the end of his soon-expiring contract. The result was no love lost between coach and owners—and a major subplot to the Raiders-Buccaneers encounter in the following Super Bowl.

“Basically, it was an all-Jon Gruden Super Bowl—he had both teams,” LaMonte says. “It was storybook. That will never happen again.”

As for nevers: About the only way LaMonte can be sure he won’t attend a Super Bowl is if two of his head coaches face off, he says. That would be too difficult.

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