The NFL's Kingmaker

How did a Bay Area high school history teacher become the powerbroker for some of the NFL's top coaches? By thinking big while keeping his business small.

By Jason La Canfora /

The NFL's Kingmaker
How did a Bay Area high school history teacher become the powerbroker for some of the NFL's top coaches? By thinking big while keeping his business small.

The two friends, history teachers and emerging assistant high school football coaches by trade with growing young families, barely had a few extra quarters to scrape together before payday. It was a Thursday night, paychecks would come on Friday, and Bob LaMonte and Mike Holmgren were having their weekly get-together to discuss their team's upcoming games after another week of long hours teaching, conducting practices and dissecting film.

It was the late 1970s in the Bay Area, and a pitcher of beer would set you back a few bucks. This constituted a significant splurge for the buddies, who had distinguished themselves as high school athletes themselves in the region in an earlier time and were focused on their burgeoning high school coaching careers. The prospect of conquering the world of NFL football, as both would go on to do in their fields, wasn't even conceivable at the time. Instead, they dreamed on a much smaller scale of a world where the beer might flow more steadily, and perhaps even be accompanied by some munchies on occasion. Neither could have imagined the improbable football journey that awaited.

"We would go to a pub and pitchers were like $3, and we had a dollar each, so we could each get a beer," said LaMonte, speaking from what his family now affectionately calls "LaMonte's Pub," a beautiful man cave in his home about a par five from the Pacific Ocean in Half Moon Bay. "And I remember many times we'd sit back there and say, 'Wouldn't it be great if someway, somehow we could come in on any Thursday before Friday payday and each get a pitcher, buy some beer nuts and leave money for a tip?' And we looked at each other and said, 'That'll never happen.'"

Oh, but it did. And so much more.

The two near-lifelong friends can joke about it now, and often do, recalling their humble roots with joy and endearment. But when they do so these days, it's usually from an exclusive private residence or possibly off the coast of the Mediterranean or maybe from a suite at the Super Bowl. To say that they eclipsed their modest goals would be quite the understatement, with LaMonte going on to become one of the most powerful agents in the NFL, a true kingmaker, and a pioneer in the booming business of representing coaches and front office executives. And Holmgren, his first coaching client, only became one of the most successful offensive minds of his generation, a Lombardi Trophy-winning head coach in Green Bay and a possible future Hall of Famer whose robust coaching tree continues to bear fruit.

Not bad for a couple of high school teachers.

"It's just an absolute miracle," LaMonte said, "because if you would have ever said to us in the late '70s that we would be having any sort of discussion like this, I would have said it was impossible. And he would have said the same."

"It was a time in our lives where we were still trying to figure out what we wanted to do long-range," Holmgren said. "And looking back at how hard it was financially -- we were all teaching school and had young families -- to where we are now, and seeing our kids grow up, and where they are, and the experiences we've had, it's fun to look back on those days. And we do it every chance we have."

In reality, none of this was planned. No one could have predicted where this story was going.

LaMonte stumbled into the business organically, asked by players he had coached in amateur sports to serve as their representative. He never fathomed he would become a powerful agent. It remained a side-job for him and his wife, Lynn, for almost 20 years, until all of their children were college age, with business booming and culminating with Holmgren becoming a head coach with the Packers in 1992.

Mike Holmgren was the first of Bob LaMonte's clients to land a top NFL job. (Getty Images)

It was at that point that LaMonte walked away from teaching and coaching (and selling real estate and insurance on the side), stopped representing NFL players (his clients include former first-round picks, starting with Bay Area quarterback Rich Campbell, as well as a handful of ace starting pitchers, beginning with Dave Stieb (another Bay Area product), and made a salient decision to alter his business model. It was then that he shifted to the nascent field of coach/executive representation, unsuspectingly building an empire in the process.

In that time he has cultivated the careers for some of the winningest coaches of salary cap era, Andy Reid and Jon Gruden among them. He has serviced over 120 clients, negotiated over $1.6 billion in contracts and come to be recognized as one of the more influential powerbrokers in the league. He has also thrived representing college coaches, most notably securing a record contract for Charlie Weis with Notre Dame.

In the past few weeks alone, LaMonte placed clients in two of the more coveted jobs in the league, with Ben McAdoo assuming control of the Giants and Doug Pederson going the Eagles. It is not uncommon for the coach, coordinators, general manager and team president of some clubs to be part of LaMonte's Professional Sports Representation family, and at one point a decade ago he represented a quarter of the active head coaches in the NFL.

It is impossible to trace the history of Holmgren's branch of Bill Walsh's West Coast Offense tree without seeing LaMonte's imprint and at age 70 he and his wife are showing no signs of slowing down as they prepare to take in Super Bowl 50 in Santa Clara, very much in their backyard.

"It's been truly amazing," said Lynn LaMonte, who has been with Bob for 38 years and has played an integral role in growing the company, working with client's wives and family and helping them make strategic financial decisions. "Our company is a little bit different, too, because we're a bottom-up company -- so we build as we said organically and take a holistic approach. We take care of the whole versus a part, and it's just been great. We're blessed to work with our clients and we've had fabulous athletes and their wives, fabulous coaches and their wives and fabulous GMs and their wives, and we're truly are blessed and humbled by the people we work with."

Leaping out into the unknown

It began, humbly, of course.

The LaMontes have four children (Lisa, Lori, Valerie and Brian) and this is very much a family business, a true Ma and Pa shop. Education was in their blood -- Lynn was a speech pathologist before devoting herself entirely to PSR -- and sports was a constant in their lives. LaMonte was gaining a reputation as a top prep coach in the area and he had long known of Holmgren (they are separated by three years and grew up just 10 minutes apart), a top high school quarterback in the area who went on to USC and was drafted in the NFL's eighth round in 1970 before getting into teaching and coaching himself. LaMonte played nose tackle at Santa Clara, later earned his master's degree in U.S. Diplomatic History/Labor History from San Jose State and went on to teach history and coach varsity football at Oak Grove High School in San Jose.

Their paths dovetailed -- LaMonte left Oak Grove in 1973 to become the head of the social science department and to coach football at nearby Santa Teresa (where he would remain until 1992) while Holmgren was on his third coaching/teaching job by 1975, taking over as an assistant coach at Oak Grove (where he would remain through 1980). Their friendship blossomed during these years and they would go on forge an incredibly prosperous business partnership as well.

By this time LaMonte had coached some of the best local athletes during a rich time for Bay Area talent, including Campbell, the top quarterback in the area. He also got to know Stieb (Oak Grove class of 1975), who would go on to become one of the top pitchers of the 1980s with the Toronto Blue Jays and would eventually ask LaMonte to represent him as well. (LaMonte would later come to represent Cy Young award winners Pat Hentgen and Chris Carpenter, too, among others).

Longtime Blue Jays pitcher Dave Stieb was among LaMonte's first clients. (USATSI)

After LaMonte coached him at Santa Teresa, Campbell starred collegiately at Cal and was emerging as one of the top prospects in the 1981 NFL draft.

"The epiphany of this is so strange," LaMonte said, "because without Rich I would have never been able to represent players in the National Football League. And without Dave I'd have never represented players in Major League Baseball. And, definitely, without Mike Holmgren we wouldn't be having this conversation today, because he every bit launched our coaching career in representation … Having gone to Oak Grove High School and been in the same company with Rich Campbell and Dave Stieb and a Mike Holmgren was absolutely miraculous."

Campbell and his family had become fond of LaMonte from his time coaching and teaching, and were interested in working with him leading up to the draft. Meantime, Holmgren, who won a state section championship as an assistant coach and was gaining a reputation as an elite prep coach, was mulling an opportunity to make the leap to the college ranks at nearby San Francisco State. So around 1980 Holmgren asked LaMonte to meet him at the Jack Tar Hotel in San Francisco, where a high school coaching conference was taking place, to discuss his future.

"As you look back on it, it's the story of an adventure," Holmgren said. "We were both leaping out into something a little bit unknown. Being a high school history teacher -- and he taught history as well -- and coaching football, those were good jobs and we liked working with that level of young person and those kids. But then we wondered, maybe we can do this, maybe we should try this. And it's fun to dream. And I was fortunate to have him, and hopefully he feels like he was fortunate to have me to encourage each other into taking that next step to try to fulfill that dream."

LaMonte smiles next to his old friend as Holmgren is introduced as Seattle's coach. (Getty Images)

At the time, one had to have a physical education background to be a high school head coach, and Holmgren and LaMonte were both educated in the social sciences, so there wasn't any upward mobility for them there. LaMonte had started teaching at a junior college and dabbling in real estate and insurance to supplement the income. Holmgren was mulling the college game.

"I said, 'Mike, you're brilliant, you're as good as I've ever seen ever at the high school level,'" LaMonte recalls telling his colleague. "You're young enough -- he was in his late 20s, I was in my early 30s -- and I said, 'If you're ever going to do it, you need to do it now and you need to get a leave of absence.' And I would say that other than his wife, Kathy, and myself, no one else would have thought that was a very good idea, because most people would have come to that career change not at their late 20s."

As you look back on it, it's the story of an adventure -- Mike Holmgren

But San Francisco had a strong program in the region and its head coach, Vic Rowan, had a sterling reputation, and thus Holmgren's coaching star was to quickly ascend. At the same time, LaMonte needed some advice from his friend during their hotel gathering regarding the overture from Rich Campbell. "I said, 'Do you think I could become a sports agent?'" LaMonte added. "And he said, 'I don't see why you couldn't. You've taught, you've played, you've coached, you've counseled. I think you'd be great at it. You have a great business mind.' He said, 'I think you should do it.' And the rest is just history. Fifteen years later he's the Super Bowl winning coach with the Lombardi Trophy and I'm standing next to him."

As Holmgren recalls it: "At one of the breaks we're having a cup of coffee or something, and he goes, 'I think I want to be an agent.' And I said, 'Really?' And he said, 'What do you think?' And I said, 'I think you'd be a good one; you like to talk and you're good with a dollar.' And I said, 'You know what, I think I might try to get into college coaching, what do you think about that?' And he encouraged me. So we had this give and take encouraging each other at that early stage, I remember it distinctly, about maybe trying to do a little bit more in our careers."
A word-of-mouth business

In the early 1980s, any suggestion that either man would attain these heights still seemed to defy belief. A long, unique road remained ahead.

LaMonte and Holmgren had no business arrangement yet, but as LaMonte began navigating his way through the world of contract negotiations and Holmgren began moving up the coaching ladder, their careers were destined to more formally intertwine. After a year as a coordinator at San Francisco State Holmgren ended up as quarterbacks coach at BYU (with a future Hall of Fame pupil in quarterback Steve Young and a coaching graduate assistant named Andy Reid), and then it was on to Walsh's legendary staff with the 49ers in 1986, where LaMonte began officially representing the coach.

Representing coaches wasn't something that was done much, if at all, in the 1970s and 80s, and LaMonte was focused on players at the time, when he wasn't teaching and coaching and helping to raise his family. Campbell ended up selected sixth overall by Green Bay in 1981, and while his pro career fizzled -- he was out of the NFL by 1985 -- LaMonte's side job was taking off. He began meeting the major power players in the NFL business world, with Campbell such an elite prospect, and his education into the business was underway.

"I don't know how I would have had the legitimacy to be a high school history teacher -- and I taught at a junior college as well -- to go from that venue and become a sports agent, was, I think next to impossible," LaMonte said. "And I think that most people would have bet against it. Back in that day there were not a lot of agents to begin with, and that was definitely the launching pad."

Reid remembers how Holmgren would rave about his friend in the very early days, back at BYU. LaMonte, who has served on the Executive Board of the Tisch Center at NYU and is a distinguished lecturer, was kind of a mysterious figure back then, but Reid knew the would-be agent had Holmgren's complete trust.

"He was like the greatest history teacher in Northern California," Reid said, exaggerating a bit. "He's got like 15 awards for being a history teacher. That's where I knew him from."

Reid, too, could not have imagined how their lives would intersect forevermore. "I call him Coach, that's what he is," Reid said. "Right now he's a life coach, but before that he was a football coach, and a history teacher."

The next pivotal moment came when Stieb, who went on to junior college and then Southern Illinois after Oak Grove before being selected by Toronto in the fifth round of the 1978 amateur draft, was contemplating a change of representation. Stieb reached a contract impasse as an emerging force for the Blue Jays' rotation and salaries in baseball were starting to soar. The pitcher wanted someone he knew viewed him as more than merely a client.

Stieb was becoming less enthralled by his current full-time agents and LaMonte stressed to him that while he would gladly throw himself into the task, he was a part-time rep while teaching and raising the kids. He did not have the manpower and resources of some other agencies just yet.

"He said, 'Would you help me?'" LaMonte said, who remains close to the pitcher with his Reno office not far from where Stieb resides. "And we were blessed to be able to do it with a person of that caliber and basically went to Toronto and did what they called 'The Treaty of Toronto.' It was a situation whereby we all of a sudden found ourselves in the midst of being with one of the best pitchers in baseball in that period, and, once again, were blessed to have that opportunity."

The deal was somewhat revolutionary in the baseball world, and perhaps unprecedented as well, an 11-year pact completed prior to the 1985 season, worth a minimum of $16.6M and a maximum of $25M (significant totals for that era) and which Toronto eventually renegotiated in 1991, as the market had radically changed by then. LaMonte would go on to represent Hentgen, another top Blue Jays starter, and eventually World Series winner Chris Carpenter as well, among his top baseball clients. His football roster was expanding, quickly, too, which made for some unique office dynamics.

Take for instance when LaMonte was brokering a move for receiver Mervyn Fernandez (yet another Bay Area product) from the Canadian Football League to the NFL in 1997, he had one of those notorious run-ins with Raiders owner Al Davis, another Bay Area football fixture he would routinely encounter (particularly over Gruden's eventual extrication from Oakland to Tampa via a blockbuster trade). The deal was somewhat complex and Davis was accustomed to getting whomever he wanted on the phone, whenever he wanted him. That was a little difficult given LaMonte's teaching schedule.

As LaMonte put it: "You can't get a lecturer out of a lecture." Davis put the edict to the test, calling and occasionally badgering the secretaries at the junior college where LaMonte was teaching history, and refused to take any calls.

"I'm in the middle of a history lecture and I've got 150 people out there and I've got a microphone and I'm talking to them, and (Davis) went nuts," LaMonte said. "And I remember he called me afterwards and he said, 'What in the heck?'"

LaMonte went on to tell the bullish owner that it might be the illustrious Al Davis calling him, but he's not leaving a lecture for him.

"He said, 'I'm never going to deal with a history teacher again in my life in this business,'" LaMonte said, grinning a bit as the two would become regularly adversaries across the negotiating table until Davis passed away. LaMonte's client, Jack Del Rio, was hired by Davis's son, Mark, to coach the team in 2015.

The job would require LaMonte to jet around more, closing deals, meeting with clients, but they always kept it a referral business. It was word of mouth and, for the most part, they didn't come to you. You came to them. Lynn had to hold things up at home, but the priority remained on their family and their regular jobs through the 1980s. There was no master plan, so they went along for the ride, focusing on full-service client management including assistance in financial planning, marketing, whatever was necessary.

"One thing I think you find in this industry," LaMonte said, "which really, if we've been at least associated with pioneering it, the one thing I'm proudest of that Lynn and I have been able to accomplish is that very thing. When you have a family business, it's either a family business or it isn't. And in 38 years you can't fake it. We're an open book. I mean, everyone knows that and I think the biggest difference was that people understand that we got into for, I believe, the right reason: We were asked. Had we not been asked into the business we may never have evolved the way we did. But we were always concerned with that."

Taking up for coaches

The next step in that evolution revolved around Holmgren's ascent. LaMonte got to know Walsh and his staff quite well as Holmgren moved from the 49ers quarterbacks coach (1986-88) to their offensive coordinator (1989-1991). His friend was coaching nearby, and LaMonte also became well acquainted with the men he was coaching with and became increasingly intrigued by the possibilities of representing coaches and management types.

Holmgren turned down an opportunity to explore a head coaching opportunity with the Jets because he didn't want to move his family and uproot his kids from their school ("for very much the same reason we decided not to go full-time with our agency," LaMonte said) and he could see a that a market would eventually burgeon for his services.

"We had begun to notice as coaches would talk to us about what coaches got paid, and what the salaries were, that coaches really never had the opportunity to negotiate," LaMonte said. "You were given a contract, and signed it. That was it."

He knew there was clearly a pay imbalance going on, stifling wages, with coaches working ridiculous hours sans real fiduciary advancement. In the late 1980s, by LaMonte's calculations, head coaches were earning an average of $300,000 a season. It's now roughly $4M, with LaMonte's work helping drive that figure.

LaMonte knew that there would be longstanding opposition to anyone taking up their cause, with owners accustomed to quickly hashing out contract terms with head coaching candidates themselves, with agents used primarily to give a read or two over the final contract language. LaMonte still vividly recalls the time no less than Al Davis implied he would be "out of his mind" to go into the coaching business, invoking the "25/25 Rule," which revealed the long-held view that an NFL team could generally find no shortage of 25-year old coaches willing to work tirelessly as assistant coaches for $25,000 a year.

As a high school coach himself who would stay up until midnight splicing together eight-millimeter film for very little compensation, LaMonte could recognize a certain logic in Davis' sentiment, but, still, with the business of the NFL on the rise, something felt askew. Things crystallized after a frank conversation one day with esteemed offensive line coach Bobb McKittrick, a staple of Walsh's staffs.

This was a man who had taught his ridiculously productive techniques about blocking and run-game execution to guys like Mike Shanahan and Holmgren and even to Walsh -- to some extent. And in the early 1990s, at the height of San Francisco's dominance, LaMonte came to discover the coach had virtually no negotiating power. When LaMonte asked about how negotiations went on his last contract, he was told there was no negotiation.

"Bill (Walsh) slides a contract over to me, and then I sign it," McKittrick told the agent.

So LaMonte asked about benefits and pay raises and McKittrick gave him more or less a blank stare. LaMonte was a bit incredulous -- this was a dynasty in San Francisco, winning with stunning regularity -- which was when the coach explained he would get "a rollover" of his one-year contract the following year if the 49ers had done well the year before, and, if has lucky, a "bump." So, LaMonte, obviously, was compelled to explore what precisely a bump entailed.

LaMonte helped Mike Holmgren become one of the NFL's highest-paid assistants in short order. (USATSI)

"He said, 'Well, as an example, if I was making $85,000 -- and this is $85,000 in the Bay Area -- I might get a bump,'" LaMonte said of their conversation with the grizzled coach, a former Marine who took no crap from anyone, "and if I got a bump a bump would probably be to $87,500."

LaMonte did a double take.

"You get a "2,500 pay raise? And he said, 'Yeah."

So then LaMonte proceeded to ask about specific contract language, benefits, etc, getting a blank stare in response.

LaMonte asked, "Do you even read it?" and McKittrick, as expected by this point, did not. "So I said, 'It's safe to say, Bobb, that if they called for a lobotomy and castration, you'd have to do it?' And he said, '... Yeah, I think so.' That's when I knew Lynn and I had a niche, and if we could fill it we'd be successful."

Holmgren, his children grown, was just about to fly from Walsh's nest for Green Bay, bringing a talented staff with him, where he would reinvigorate that dormant-yet-historic franchise to the pinnacle of the league for the first time in 29 years. And his agent was about to build an empire.

Going all in

By the time Holmgren was ready to move to Green Bay, once again LaMonte was in lockstep. It was time, after 25 years in teaching, after sensing the seismic shift that would come to pass in coaching salaries (and the margins are much higher in the percentages coaches pay agents versus players), and with his eldest child heading to college, PSR went from part-time calling to full-time vocation. Coaches would be their focus moving forward, and it just so happened that Holmgren was putting together a star-studded staff of his own with the Packers, many of whom, and along with their brothers and sons, would go on to become future NFL coaches, guided by LaMonte.

"In those days assistant coaches, you didn't have agents, you didn't have representation," Holmgren said, "and almost everybody in the league worked on one-year contracts. And you were paid whatever they paid you, and you never really thought very much about it. And then I had a chance to become a head coach, in which case there was a whole different level you were talking about with salaries and different things. And at that point I asked Bob would you come over and talk to me about this."

Reid, who first worked with Holmgren back on that BYU staff in 1982, came over to Green Bay as tight ends coach, and even then he could tell there was something special about him. Things changed with their high-strung head coach when LaMonte was present.

"Really, when I first met Bob in person was at Green Bay," Reid said. "When we were there he would come in and hang out and we loved when he came in to training camp. it just calmed Mike right down. They'd go do their thing, go out to dinner, and Mike would be very relaxed and it was all good when Bob came in. I got to know him at that time, and Mike Holmgren has always taken care of me and he introduced him to me."

"I call him Coach, that's what he is," -- Andy Reid

Holmgren's offensive coordinator, Sherman Lewis, would become part of LaMonte's family as well, ending up logging 14 years as an NFL coordinator and a finalist for several head coaching jobs. Oh, and there was a quality control coach on board, a coach's son himself, named Jon Gruden. Gruden and Reid remain PSR mainstays, as was defensive coordinator Ray Rhodes, another future NFL head coach.

When Rhodes left to become head coach in Philadelphia in 1995, Fritz Shurmur took over as defensive coordinator in Green Bay. His nephew, Pat, remains a LaMonte client and was the head coach in Cleveland when Holmgren took over as team president there in 2011 and was a finalist for the Eagles head coach job this offseason.

When Rhodes was let go in Philadelphia he was replaced by … you guessed it … Reid, who would go on to reach five NFC Championship Games and one Super Bowl during his distinguished career there before going on to Kansas City in 2013. That Chiefs staff includes assistants like Doug Pederson (now the Eagles head coach) and former Vikings head coach Brad Childress (who remains a trusted assistant to Reid in Kansas City), both also represented by LaMonte.

Gruden, whom LaMonte has negotiated massive deals for with ESPN since leaving coaching, first worked under Holmgren as a special assistant to the quarterback coach in San Francisco in 1990. By age 28 he was coaching receivers for the 49ers. He was Rhodes's offensive coordinator with the Eagles from 1995-97 and in 1998, none other than Al Davis made history by naming him one of the youngest coaches in NFL history.

LaMonte continues to represent Jon Gruden in his work as an ESPN analyst. (USATSI)

Eventually, came the infamous trade to Tampa, with Gruden turning around the following year and beating Davis' Raiders in the Super Bowl. A photo of Gruden and LaMonte embracing on the field after that victory is displayed prominently among the bevy of memorabilia at "LaMonte's Pub" -- it the first thing you see upon heading up the stairs to the man cave, in fact. Gruden's younger brother, Jay, by the way, is the head coach of Washington, with LaMonte responsible for the lucrative five-year deal he received from the team in 2014 despite being a rookie head coach.

That original Holmgren staff in Green Bay in 1992 also included Dick Jauron (defensive backs) and Steve Mariucci (quarterbacks) who would end up coaching multiple NFL teams as well, though represented by others. By 1995 Mike Reinfeldt, a LaMonte client, was on board as CFO in Green Bay (he would end up running other clubs and would join Holmgren in Seattle when he took over as head coach there). Marty Morninwheg (in the Oak Grove High School Hall of Fame for his years as a quarterback there) also became the new quality control coach of the Packers at that time (LaMonte would one day negotiate a deal for him as head coach in Detroit), and in 1997 Mike Sherman joined in the role Reid once held, as tight ends/assistant offensive line coach.

When Holmgren left for Seattle in 1999 (he would reach a Super Bowl there, too, losing a heartbreaker to Pittsburgh), Rhodes took over in Green Bay, and LaMonte brokered the deal in 2000 that resulted in Sherman becoming the Packers head coach (he was there through 2005), and Sherman would also have a successful stint leading Texas A&M. And on and on it goes.

Coach after coach. Family after family. Time after time. Generations entrusting their future with him.

"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. In a lot of ways, that's him. He can talk about anything. He loves people. He brings energy every time you are around him. There's no negative to him at all. He's a tough negotiator. When you talk to people who have negotiated against him, he's tough. He can hang with the best of them …

"He's captured the whole picture. He'll give you that three-years-down-the-road plan which, is tough to do, because this is a win-today league. But he can give you a three-year plan, and he's pretty accurate with it, now. I've seen it over the years.

It has become, in every way, a family business, with the sons and brothers of clients now climbing the NFL ranks, with LaMonte their steward, and while LaMonte has worked with myriad clients in coaching and management with zero ties to Holmgren, so many roots of his business reach back to him as well.

Some in the league would joke about the sheer number of LaMonte's clients who were part of Holmgren's coaching staff and front office when he was in Cleveland and even now it's impossible to walk into some NFL headquarters -- the Chargers for instance -- and not see LaMonte's clients coaching position groups and serving as coordinators, with head coach Mike McCoy and general manager Tom Telesco (who received recent contract extensions), and former Chargers coordinator Frank Reich represented by him as well.

"Believe me, you'll never see a successful agent who doesn't have brilliant talent (clients), and we were blessed to have fabulous people," LaMonte said. "You break in with a Mike Holmgren and you're going to have a hard time messing that up."

Keeping it in the family

Of course, juggling egos and managing expectations and dealing with often impetuous owners and navigating the terrain of an NFL that has become increasingly ruthless in regards to how quickly head coaches and their assistants can be tossed aside, is anything but easy. It requires a certain reputation and a fair amount of backbone and ample charisma to boot.

The staff around LaMonte has grown, but not by much, still running the crux of the business out of a modest office in Reno most of the year, and bringing in a new protégée of sorts, former Packers exec Mark Schiefelbein, in 2015 to oversee the office and help take the family business into the future and sustain its growth.

This past season, LaMonte represented five of the 32 NFL head coaches -- Reid (Kansas City), John Fox (Chicago), McCoy (San Diego), Del Rio (Oakland), Jay Gruden (Washington) -- while continuing to expand Jon Gruden's vast media reach in broadcasting. He added McAdoo (Giants) and Pederson (Philadelphia) to the head coaching ranks, putting him close to a quarter of the league again. He also represents seven of the NFL's general managers/chief of football operations: Steve Keim (Arizona), Mike Maccagnan (Jets), Jason Licht (Tampa Bay), Rick Smith (Houston), Rick Spielman (Minnesota), Howie Roseman (Philadelphia) and Telesco (San Diego). He had a host of hot coaching and general manager candidates as usual during the annual January overhaul that takes place in those ranks, including rising execs like Omar Khan (Pittsburgh) and Chris Ballard (Kansas City), and potential future coaching candidates like Sean McDermott (Carolina defensive coordinator), Sean McVay (Washington offensive coordinator) and Kyle Shanahan (Atlanta offensive coordinator).

Andy Reid, Jay Gruden, John Fox and Jack Del Rio are among the active NFL coaches on LaMonte's roster. (Getty Images)

And, if the coming months go as is normally the case, there will be a bevy of coaches and execs seeking to get time with him at the February scouting combine, hoping to join the ranks of PSR clients, while some established coaches may opt to switch over to hi as well, as was the case with Del Rio.

"In meeting with him, La Famiglia was enticing," Del Rio said of why he signed on with LaMonte later in his career. "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. Because even though he has a lot of guys he does a great job of touching base and making sure I have what I need. He's really done the best job in that capacity … The thing about Bob is you know he's always going to be in the conversation."

Each year the competition grows more intense, for what was once a cottage industry that LaMonte helped define, is now big business. With the rising costs of representing players -- who can be quite fickle -- to train them for the combine only to make often 1.5 percent of a contract and with rookie contracts essentially now slotted and not open to much actual negotiation, more and more agents are interested in representing as many coaches and executives as they can.

LaMonte will remain driven yet selective in his pursuits and is not close to ready to close the family business just yet. He's rebuffed countless inquires from mega-agencies or interested investors to sell and isn't slowing down at all.

"Somehow, he's not aging," Reid deadpanned. "I don't get it. I don't understand. There must be something in Ketel One that allows you to stay youthful, because he has not aged a bit."

Heck, LaMonte might not even be done working with his old buddy Holmgren just yet, as owners continue to mull him as a potential team president or "football czar." (LaMonte always has an ear out, as you well may have gleaned by now.) Of course, there are considerably more zeros at the end of such contracts now; they long ago stopped worrying about how much a pitcher of beer might set them back.

And there's a pretty good chance that one day the two men just might toss back a cocktail or two (Ketel One?) under a tent on a balmy night in Canton, Ohio, with Holmgren donning a mustard jacket and his buddy thinking back to how this whole unlikely story got started, and the dive bars and high school fields around San Jose that brought them together on this improbable journey.