The double agent: Meet the power broker behind Jon Gruden’s $100M deal with Raiders

Around 4:30 p.m. last Sunday afternoon, when the Oakland Raiders were putting the finishing touches on their embarrassing 30-10 loss to the Los Angeles Chargers and owner Mark Davis was informing Jack Del Rio that he was no longer the head coach, Bob LaMonte’s phone wouldn’t stop buzzing.

Week 17 is about as busy as it gets for the most-powerful agent for football coaches. On the eve of Black Monday, the phone calls don’t stop.

“Somewhere in the neighborhood of probably about — on a bad night — 150 to 175,” LaMonte estimated.

Largely hidden from public sight, LaMonte is at the center of the Raiders’ latest saga in which Del Rio is out and Jon Gruden is in — at a reported price tag of $100 million over 10 years.

LaMonte represents both. It’s an arrangement, which, on the surface, appears awkward at best and problematic at worst. To draw such a conclusion is to misunderstand how the ecosystem operates and how wide LaMonte’s empire extends.

Beginning with a lone client, LaMonte has built Professional Sports Representation, Inc. into the premier agency for coaches and executives in the world of football. At one point, LaMonte repped a quarter of the coaches in the league

Currently, his sprawling roster of clients includes current, prospective and recently dismissed coaches like Del Rio, Gruden, John Fox, Jay Gruden, Ben McAdoo, Sean McDermott, Sean McVay, Doug Pederson and Andy Reid. His list of execs is equally impressive, counting the executive vice president or general manager of the Houston Texans, Indianapolis Colts, Kansas City Chiefs, Los Angeles Chargers, Minnesota Vikings, New York Jets, Philadelphia Eagles and Tampa Bay Buccaneers.

“We’ve been blessed to have great, great clients,” LaMonte said, when asked to explain how he keeps up with all the demands.

He also credits his wife, Lynn, the vice president of PSR.

“My wife and I started this business 40 years ago,” LaMonte continued. “This is our 40th year and we were just fortunate because we never had to recruit. We had these great clients. And if you have that, it makes it work, but we’re humbled by our chances and blessed to have the opportunities we’ve had.”

In the niche industry he pioneered and has gone on to dominate, LaMonte’s first client was Mike Holmgren — a lifelong friend who would connect him with so many other coaches, like Gruden and Reid.

Before Holmgren was the Super Bowl-winning head coach with the Green Bay Packers, both he and LaMonte had been high school teachers and coaches in San Jose. By 1986, Holmgren had risen to quarterbacks coach for the San Francisco 49ers. LaMonte was his agent and in 1990 Gruden was his special assistant.

At Holmgren’s next stop in Green Bay, Gruden and Reid were both on the staff. The trend of scooping up assistants has been a hallmark of LaMonte’s business. Greg Olson (not the tight end) and Paul Guenther — reported to be Gruden’s offensive and defensive coordinators, respectively — are also both under the PSR umbrella.

Reid referred to LaMonte as a regular renaissance man in a profile by CBS Sports.

“He’s brilliant, first of all,” Reid said. “And he’s a great people guy. There is nothing he can’t talk about. He’s like the Dos Equis guy — ‘Stay thirsty my friend’ — that’s Bob.”

LaMonte’s personable style is immediately apparent. He’s genuine and friendly. His skills as a negotiator are impossible to dispute. In his career, LaMonte has brokered over $1.7 billion in contracts. 

The client names and dollar figures are large, but that’s it. The slogan on the PSR website — which lists just five “team” members — explains it all.

“We are not a big-time sports agency, we just represent big-time people.”

PSR is headquartered out of an office in Reno. LaMonte also has a home in Half Moon Bay.

“We don’t have high-story buildings in New York, San Francisco and Chicago,” LaMonte said. “We were just a mom and pop store that opened up in the Bay Area and we were blessed that over time it grew into something quite dramatic.”

That family style is what initially brought Del Rio to LaMonte’s agency.

“In meeting with him, La Famiglia was enticing,” Del Rio told CBS Sports. “I’m happy to be with him. I think he did a great job … Honestly, that’s why I didn’t go with him at first, because he has so many people and you wondered if he could give you enough attention, but that couldn’t be further from the truth.”

In the coming days, LaMonte will have to provide that attention to the now out of work Del Rio, but first, he’ll be back in the Bay for Gruden’s introductory news conference on Tuesday, which reportedly will be “splashy.”

Then it will be back to the shadows for LaMonte who will continue to spin the coaching carousel and never reveal more than he has to.

“Well, one of our mottos is, ‘Omertà.’ I’m Irish and Italian. I’m Sicilian,” LaMonte said. “Omertà’s a code of silence. We don’t really talk to too many people too many times.”

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