The many faces of Jon Gruden

The man I knew, the man he became, and the shell of a man he is now

Today, I shall take a detour from the world of comic books with the topic du jour — but let’s say that the comic book industry can continue to grow and prosper by taking a hard look at what went down with disgraced NFL head coach, Jon Gruden.

Just before the turn of the century, I was a fresh-faced college kid, taking classes toward my journalism degree at a state school and waiting tables at a TGI Friday’s in Pleasanton, Calif. That’s the first time I encountered Oakland Raiders head coach, Jon Gruden. He came to the restaurant with his wife, Cindy, and two young boys, Deuce and Jayson. I brought food to his table, I helped him order some extra goodies for his little boys and we had a nice chat about my lifelong passion for all things Raiders. His wife complemented the Raiders buttons I wore on my ridiculous work uniform.

What struck me most about that first encounter was the way he greeted me on the way out of the restaurant. I held the door open for his family and he came right at me, smiled and thanked me, then he did what only a football coach would do to one of his players. He gave me a strong, stiff pat on my side, just below the ribs, just above my hip - a soft spot reserved for coaches and players to show affection in the manliest of ways. I knew this gesture so well, having played and coached organized football, and staying close to it as a young professional. He made me feel like a player again — I was energized and mesmerized, like Marcia Brady vowing never to wash her cheek again.

The next time I met Coach Gruden was at his first training camp at the helm of the legendary silver and black, held at the Napa Valley Marriott in the Northern California’s wine country. I was a cub reporter, filing a training camp special for my college TV station. Upon entering the walls of the practice field, Gruden’s voice boomed across the practice fields. “I need Charles Woodson on punt return!” “This isn’t the Peach Bowl now, this is the N-F-L!” My camera man and I were entranced by this Napoleonic figure dominating everything in his path.

After practice, he was gracious enough to grant me a 1:1 interview, which was a big deal, but I was so green I didn’t even know how coveted this was. He was kind and gracious, answered all of my questions in a very down-to-earth way. After we finished the interview, he looked me in the eye, shook my hand, and said “nice to meet you, Omar.” I didn’t dare tell him we’d met earlier that summer at TGI Friday’s.

My third encounter with Gruden during his first year with the Raiders was in the TV studios of KRON-TV 4 in San Francisco, where I was a sports intern, working a couple of shifts per week for school credit and parking money. Gruden was the guest of legendary sportscaster Gary Radnich, on his popular Sunday-night sports interview show. The rookie head coach was so new to the spotlight, he had a hard time looking at the right cameras at the right time under the glare of the studio lights. He was charismatic, but he was far from polished as a TV personality. Again, the coach was kind and warm me to me, an intern with no name and no pelts on the wall. In that setting I was reserved and professional, as it was frowned upon to ask for photos or autographs inside the hallowed walls of an NBC affiliate station.

This was the beginning of the end of Gruden, the approachable and affable young coach. He quickly became a media sensation, appearing on the cover of People magazine and sitting on Jay Leno’s couch on late-night TV.

By the time I returned to training camp in Napa a few years later, now a full-time reporter at a local cable TV station, I could see that the man had hardened. In the gang-bang style media interview session after practice where he was swarmed with microphones and cameras, I noticed a marked difference. The warmth and the light in his eyes was gone - they were lifeless and cold. He answered questions with disdain and impatience. I chalked this up to the wear and tear of being under the iron fist of Raiders owner, the late great Al Davis.

I started hearing rumors about a rift between him and Davis. A rift fueled by jealousy of Gruden’s popularity but also swirling gossip about a courtship from college teams like Notre Dame and Florida. There were also whispers that Gruden was carrying on an affair with a young Raiderette cheerleader at the Oakland Airport Hilton, a hotel where Davis roamed the halls like a nocturnal crypt keeper and where Davis ultimately died. This affair with the cheerleader was allegedly happening at the time his wife (a former college cheerleader) was pregnant with their third son, Michael.

Many years later, Tom Cable became the head coach of the Raiders and was publicly disgraced as someone who beats women. Davis held a press conference where he strongly hinted toward something about Gruden. Without naming him, he said he’d already dealt with this sort of issue before, with a previous head coach “who you all thought was great,” and who had a domestic disturbance involving the police at his home. Davis took the details of that innuendo to his grave in the Oakland hills.

By all accounts, Gruden became insufferable after he won the Super Bowl as head coach of the Tampa Bay Buccaneers in January of 2003. Now divorced from taskmaster Davis and the Raiders, he ran roughshod over the Tampa Bay ownership and general manager, Rich McKay. Gruden brazenly took his players to Hooters in the offseason and held court among the chicken wings, beer, and tank tops. Tampa Bay eventually fired Gruden after losing to Cable and the Raiders on the final game of the 2008 season.

Gruden started the “Fired Football Coach’s Association” near Tampa and it became a clinic, or lab of sorts, where players and coaches could break down game film with Gruden. That lab became a televised ESPN goldmine, with a series called Gruden’s QB Camp. That show propelled Gruden into the booth of ABC/ESPN’s legendary Monday Night Football broadcasts. Just like John Madden (another Pleasanton resident and former Raiders coach) before him, Gruden became a household name on prime time TV.

It was during his rise to super-stardom that Gruden wrote all of those infamous e-mails filled with racism, homophobia, and misogyny, as reported by The New York Times over this past week. By then, he was a lost cause, a cartoonish representation of the macho culture of football. I know this culture; I lived it as a teenager with coaches that I idolized and probably shouldn’t have. That football bug is still one that lives with me to this very day — I miss the discipline, the competition, and the camaraderie of a locker room. But with that brotherhood comes the dark side of football; the testosterone, the bullying, and the risk of permanent damage to the mind and body. I’ve had a football concussion; it was scary and no one should be critical of the NFL when it comes to player safety.

Gruden was already broken beyond repair by the time he came back to coach the Raiders in 2018. This is when I had my final encounter with a man I could barely recognize as the young, charming 34-year-old wunderkind coach back in the day. Gone were the days of my dad and brother bumping into Gruden at a Burger King in San Leandro, or at the aforementioned Hilton, where he was glad to shake hands and take pictures. Gruden 2.0 was a paranoid, political nightmare of a one-man media conglomerate.

He was a head coach, part-time offensive coordinator, defacto GM, and still a TV pitchman, with designs on owning part of the Raiders one day. He wanted it all - and believed that he could have it all. He was privileged and entitled.

My last brush with Gruden’s fame came at the legendary Ricky’s Sports Bar in San Leandro. Before the 2018 season, Gruden hosted a party for Raiders fans where he paid for everything: food, beverage, t-shirts, pre-autographed photos, and other swag. It was like Elvis had resurrected and re-entered the building. Gruden was mobbed.

The man was emotionally drunk and delirious from the power and adulation he commanded. I contributed to that — I was there as a fan, long-done with my days as a member of the media. I observed him closely and watched his every move. He was sweating profusely as he moved from room to room with his bodyguards desperately trying to keep hoards of fans off of him. He couldn’t keep his attention on anything, or anyone, his eyes were darting about all over the establishment. He was manic. As he would fling t-shirts into the crowd, he would pant and grunt; he looked twitchy, like a methhead. It was like watching a drug addict go through withdrawal and an overdose all at the same time.

Admittedly, I followed him around from room to room around the brick-walled establishment. I finally caught up to him and had him sign my throwback Oakland Raiders, New Era cap, with the small block-lettered “Oakland” and “Raiders” in large script font. That day, the hat may as well have been made of silver, but today it isn’t worth a lump of black coal.

When the Raiders re-hired Gruden it sent a jolt of euphoria through the Raider Nation that spread all the way around the world. it didn’t matter that the Raiders fired hometown hero Jack Del Rio in order to make room for the return of the man nicknamed Chucky. I had season tickets for that first season Gruden was back on the sidelines. I ended up going to only one game because I was so disillusioned with Gruden 2.0 as that 2018 team limped to an uninspired 4-12 finish. The man who received a 10-year, $100 million dollar deal to the return the Raiders to greatness did not get the job done. He once quipped that if he didn’t get it done, he would return the money to the Davis family. Now he leaves the franchise in chaos. He is disgraced and probably black-balled by the game he squeezes so tightly it has slipped through his greedy fingers.

The rise and fall of Gruden will be chronicled and analyzed to death until his name is no more than a cautionary tale. For me, it was important to chronicle my observations of a man who I used to identify with — an undersized man who loved playing the game, but with too many physical limitations to continue on as a player. He was a man that tried to stay close to the game by coaching it, broadcasting it, and ultimately trying to bend it to his will by criticizing a commissioner that took him down like a corporate mob boss. I was a man that tried to stay close to the game through TV journalism, but ultimately had to let go. I had to grow up and move on, something Gruden never did, even as a man approaching retirement age.

Long ago, I abandoned my obsession for football and TV news, and instead focused on my other passions: family, starting my own family, and creating comic books about virtuous characters who would never let me down as badly as Chucky did. I do find some of the same bro-culture being rooted out of the comics business, with public take-downs of bad actors that display the same entitled, racist and misogynistic behavior. It is for the best… be it football, comics, or any other fandom and community. I doubt I’ll ever run into Gruden again in my life, and it’s probably better that way. I pray I never encounter a tragic, Gruden-like person in the professional world of publishing and entertainment.

Thank you for reading and listening to me through this cathartic trip down memory lane. I close this chapter having learned from it, and I move on.

With pride and poise,