Your quality of work is simply wonderful.
How Dennis Gilbert Went from the Dirt Fields of South-Central L.A. to the Best Seat in the House
By Larry Stewart
For once, Dennis Gilbert wasn’t wearing a suit and tie, or even a sports coat. Slacks, shirt and jacket fit the occasion. It was a weather-perfect Saturday in the fall of 2017, and a rare day off for him.
The man nicknamed "Go Go" has spent most of his adult life on the go, working nearly 24/7. And almost always immaculately dressed.
But on this day, he appeared relaxed and comfortable at his Holmby Hills home in the ritzy part of Los Angeles as he greeted this sportswriter, whom he had known since 1969, and photographer Rich Kee.
We were there to do a profile on Gilbert, something different than the many stories done on him during the ’80s and ’90s, when he was among the most prominent player agents in baseball. In 1993, USA Today, in a headline, called Dennis "THE MOST POWERFUL MAN IN BASEBALL." The Sporting News called him the 12th most powerful man in baseball, which is still impressive.
Our objective in this space, as we launch Ultimate Game Faces, was to find out how Dennis Gilbert became, well, Dennis Gilbert. Instead of rehashing some of the stories about his success selling life insurance to the rich and famous and negotiating historic baseball player contracts – such as the one in 1992 for the San Francisco Giants’ Barry Bonds that ended up paying more than $50 million over six years -- my plan was to ask Gilbert questions about his life’s journey.
I wanted to learn about his lean years, about how he got started in the life insurance business, about how he was able parley that success into his success as a baseball player agent. I also wanted to learn more about how Gilbert did an about-face and became an executive with the Chicago White Sox while continuing to live in Southern California.
I thought I knew Gilbert well, but during a two-hour interview and photo shoot at his home, I learned even more.
His story is one 19th century author Horatio Alger might have written about in one of his novels, which featured persons of meager backgrounds who, through hard work and ingenuity, rose to great heights.
When we arrived at the Gilberts’ home, Dennis’ wife Cindi, the perfect hostess, already had prepared a modest spread that included bagels, lox and cream cheese. And coffee had already been brewed. We met in the tennis house on the 1.3-acre estate, where we could look out over the tennis court at a pool where tropical fish were swimming. The pool for humans is further up on the property. We would have met in the main house, but it was in the middle of a major remodeling project.
The Gilberts moved to Holmby Hills in late 2012 to be closer to Dennis’ Beverly Hills life insurance office. Their previous home was a 12,000-square-foot, seven-bedroom, nine-bathroom, two-story mansion in Hidden Hills West near Calabasas. It served as part living quarters, part baseball museum, part entertainment complex.
It was a perfect place for parties, and the Gilberts had lots of them there. For Dennis’ 60th birthday in 2006, the Temptations performed on the tennis court. The "warmup act" was multi-talented sportscaster/entertainer Roy Firestone doing what he calls his "musical salute to sports and entertainment," which includes singing, impersonations, jokes and sports bloopers. Later in the evening, Stevie Wonder, who lived next door, came over and sang happy birthday.
These days, Gilbert, who as a youth envisioned becoming famous baseball player, is a famous baseball spectator.
During game telecasts at Dodger Stadium during the 2017 baseball playoffs, Gilbert may have been seen on camera more than any of the players on the field. Whenever Fox or TBS showed a batter at the plate from the usual camera angle from behind the pitcher’s mound, more often than not, there was Dennis’ face.
Viewers in Los Angeles who regularly watch Dodger games have gotten used to it. He’s the dark-haired man in glasses, usually dressed in a suit. He rarely misses a game. Around Dodger Stadium, and sometimes away from the ballpark too, Dennis gets stopped asked, "Hey, aren’t you the guy who sits right behind home plate?"
Initially, people would ask for a selfie or an autograph or both, then might ask, "Who are you?"
He would smile and say, "I’m Dennis Gilbert."
In more recent years, Gilbert usually doesn’t have to identify himself. Most people who approach him know his name.
But Dennis Gilbert is much more than "the man behind home plate" who, by our estimation, pays more than $250,000 a year for four front-row seats in the Dodgers’ exclusive Dugout Club. He generally uses the seats to entertain current and prospective clients, but sometimes his guests are just friends. And he has lots of friends.
Gilbert is also the man behind the Professional Baseball Scouts Foundation, which in its first 14 years of existence raised more than $2 million to help current and former baseball scouts in need. The foundation’s marquee event is its annual fundraiser gala, titled In the Spirit of the Game. It always draws a capacity crowd that includes many Hall of Famers and baseball dignitaries.
The 2018 edition, the 15th annual In the Spirit of the Game dinner, is scheduled for Saturday, Jan. 13, at the Beverly Hilton Hotel, the event’s original site. Among those receiving awards that night will be Bryce Harper, Ken Griffey Jr., Buster and Kristen Posey, Terry Francona and Thomas Tull, the legendary film producer who likely is future major league owner.
As for Gilbert, he is also the man behind Dennis Gilbert Field, a baseball diamond in South Central L.A. for inner-city youth that opened in January of 2002. Gilberts’ initial donation was nearly $400,000 and that grew to more than $1 million by the time what turned into a five-year project was completed.
Gilbert, from the L.A. suburb of Gardena, isn’t someone who was born on third base and thought he hit a triple. There were down times, plenty of them. He came from a loving family, but money was scarce, particularly after his father suffered a heart attack and became disabled when Dennis was in his late 20s. After that, his father only worked on Sundays at swap meets.
During our interview at his home, I asked Gilbert when was his lowest point.
"I think it was 1972," he said. "I was living in a tiny studio apartment at Fountain and Western and sleeping on a Murphy bed that pulled out from the wall. I had just started selling life insurance, and wasn’t very good at it.
"Things were tough. I was selling furniture – my own," he quipped, then added: "There were times when I was hungry. I remember one night there were two of us who had to pool our money to buy one taco, which we shared."
While attending Gardena High, Gilbert played baseball and ran track. He was good at both. In track, his personal best in the 100-yard dash was 9.6 seconds. But baseball is what he loved. An outfielder, he began playing the sport as a young boy in neighborhood dirt fields in Gardena and South-Central L.A. At one time or other, he played with the likes of future major leaguers Bob Watson, Willie Crawford, Bobby Tolan and Reggie Smith.
He was good enough in baseball to get signed by the Boston Red Sox at the age of 19 while he was attending Los Angeles City College. This was supposed to be the first step toward realizing his dream of becoming a major league ballplayer.
It never happened. Dennis played five years in the minors. He spent the 1969 season playing center field for the Visalia Mets of the Class-A California League, making $600 a month and getting $3 a day meal money. Visalia is where I first met Gilbert. Fresh out of college, I was working for the Visalia Times-Delta, and one facet of my job was covering the Visalia Mets.
I recall that Gilbert, a left-handed hitter, could fly to first base. He was clocked at 3.7 seconds. And he was a good hitter. But I recall on occasion him misjudging a routine fly ball, coming in when he should have been going out. He blames it on a vision problem. He has worn glasses most of his life.
The late Harry Minor, a major league scout most of his life, was Gilbert’s manager in Visalia.
Years later, Minor, who lived in Long Beach, told me: "Dennis could put a bat on the ball and he had great speed on the base paths. But I told him he’d make more money doing something else. I think that was pretty good advice."
Gilbert’s last season of playing ball was spent in the Mexican Leagues, where one ballpark had railroad tracks running through the outfield. Play was halted whenever a train came along.
Gilbert came home from Mexico, and that was it. His dream of being a major league ballplayer was over. He was a lost soul and had no idea what he was going to do.
He helped coach the baseball team at L.A. City College, but he needed a job – badly. He was living out of the back of his Dodge van and showering at public beaches.
"Our first baseman’s father would come to watch his son during practice and arrive in a shiny new Cadillac," Gilbert said. "One day I went over and introduced myself and asked him what he did for a living. He told me he sold life insurance. I asked him how would go about getting a job selling life insurance. He found me a job."
But Gilbert, trying to sell $2,500 or $5,000 polices door to door, wasn’t able to make enough money to rent a decent place to live or even afford his own taco. He was frustrated, and figured there had to be a better way.
Here’s where his ingenuity came into play. He decided to try another tact. He’d go to City Hall and stand outside the county clerk’s office where marriage licenses were issued.
"When I saw a young couple and one of them had an envelope in their hand, I knew that was a marriage license," Dennis said. "What I’m going to tell you is something I’ve never shared with anyone before. I went up to these couples and told them I was the L.A. County’s life insurance broker for newlyweds."
Suddenly, Gilbert’s business improved. But not without one unnerving moment. "One day a judge came up to me and asked: ‘Are you the guy selling life insurance and claiming to be with the county?’ I thought, oh boy, I’m in trouble," Gilbert said. "But he ended up offering me a non-paying job as a marriage witness. He said these young people would come in to get married and not bring a witness. I told him, sure, I’d help him out. I can’t tell you how many marriages I stood in for."
Gilbert’s next move was to hang around hospitals and sell more expensive policies to doctors and others working in the medical field. He soon was selling as many as 200 policies a year.
At the same time, he was attending classes to learn more about the business and eventually got approved to teach classes on estate planning. Through these classes he met accountants and business managers for Hollywood celebrities. Soon he had such clients as Lorne Green, Michael Landon, and Robin Williams. They were followed by many more big-time celebrities.
By the time Dennis was 31, he was making in excess of $100,000 a year, a more-than-decent salary for the late 1970s.
One of his mentors along the way was Jordan Olivar, who in 1962 retired after 19 seasons of coaching football at Villanova, Loyola Marymount and Yale and went into the life insurance business.
"Jordan was a very close friend of John Wooden," Gilbert said. "They’d play racquetball early in the morning, then I would meet them for breakfast. Jordan provided me with the technical skills to succeed in the business and get certified to teach insurance classes."
Despite his success in the life insurance world, Gilbert’s love for baseball never wavered. On the side, he worked as a scout. In 1975, he recommended to the Baltimore Orioles that they sign Eddie Murray, who was a bat boy when Dennis was playing in the dirt fields of South-Central L.A. Murray, from Locke High School, signed with the Orioles and spent 11 of his 21 years in the majors with them and had two stints with the Dodgers.
During our interview, Gilbert found a letter he received from the Orioles, along with a $75 check. The check and the letter were a thank you to Gilbert for recommending Murray. It was Gilbert’s first baseball deal. He made a little more than $75 on later ones.
Thoughts of becoming a baseball agent lingered with Gilbert. He finally took some action in 1982. He recruited two potential partners, friends he made in the minor leagues -- former Red Sox slugger Tony Conigliaro and Bobby Brett, a brother of Hall of Famer George Brett.
Before the agency was up and running, Conigliaro, who was beaned in 1967, suffered a massive heart attack that left him in a coma. (He died in 1990.) And Bobby Brett backed out because he wanted to own a minor league team, and one can’t be an owner and an agent at the same time.
But Gilbert didn’t give up the idea of becoming a baseball agent, and in 1984 he launched the Beverly Hills Sports Council and began bringing in associates. One was an insurance client, Mike Trope, who at the time was the generally regarded as the top football agent in the country. For a short period, Gilbert also dabbled in football. But baseball was his first love and what he knew best.
Gilbert and Trope parted ways but remained close friends. "Dennis Gilbert is a sensational salesman," Trope says. "There is no way I would have bought life insurance – you’re gambling against your life – but we had dinner and I bought life insurance from him the next day. He has this soft-sell technique where you get to know him, you become buddies, and you’re sold."
The Beverly Hills Sports Council had a modest start, but survived because of Gilbert’s success with life insurance. And in just a couple of years, the firm was bringing in $3 million a year.
If there is a secret to Dennis’ success in soliciting both life insurance and baseball clients it is this: "You have to show that you are successful if you want to convince someone you can make them successful," he says. When he was starting out as an agent, he drove a Rolls, had an office in Beverly Hills, lived in Beverly Hills and always dressed to impress. "Dennis wears a suit to the beach," his friends would say.
After he was established, he downgraded from a Rolls to a Mercedes, but still almost always wears a tailored suit.
When it came to entertaining current or prospective clients, Gilbert took them to the finest restaurants or, if it was a sporting event, concert or the like, the seats were always the best in the house. Nothing impresses quite as much as front row seats right behind home plate.
Gilbert had a good run as a baseball agent, but the pace was even too much for someone nicknamed Go Go. His exit from the agent business began in early 1998 and was completed by early 2000.
It wasn’t the workload that got to Gilbert. It was the late-night phone calls. One player called because a relative got arrested on drug charges. Another player called because he drove off and left his family at the ballpark after a night game. The calls weren’t always from clients. There were those from clients’ relatives and friends who were in need of a favor. The calls never stopped, 24 hours a day.
During the 2000 baseball playoffs, Chicago White Sox owner Jerry Reinsdorf invited Gilbert and his wife Cindi to be his guests at a game against the Seattle Mariners. It was at that game that Reinsdorf, who had been impressed by Gilbert’s negotiating skills, brought up the possibility of Gilbert going to work for the White Sox and negotiating player contracts from the other side of the table.
Details were soon worked out and Gilbert was named Reinsdorf’s special assistant. A key issue was that Reinsdorf allowed Gilbert to remain in Southern California.
Reinsdorf first met Gilbert in 1985 when he represented a young shortstop named Ozzie Guillen, who 20 years later was the manager of the White Sox when they swept the Houston Astros in the 2005 World Series.
"Dennis and I immediately became good friends," Reinsdorf told Doug Krikorian of the Long Beach Press-Telegram. "He has helped us in many ways. Dennis is such a nice guy. He reminds me of a Jewish mother, always concerned and worried about everything. He’s very caring, and very generous."
And Gilbert’s baseball knowledge figured heavily in putting together that 2005 White Sox team that went 11-1 in the postseason.
As for Gilbert being generous, during our interview, his barber, a man Gilbert called Little Joe, showed up with a friend to deliver a cheesecake specially made by his wife. It was a token of appreciation. Gilbert had given Joe tickets to the 2017 World Series. "Little Joe had never been to a World Series game," Gilbert explained. Said Roy Firestone: "Dennis is one of the most philanthropic people in Southern California and a big supporter of my charity (Westcoast Sports Associates) for 24 years."
When Gilbert was playing ball in Waterloo, Iowa, he was a fan favorite because of his speed on the base paths. There were banners on the fences down the line above the dugouts that read "Go Go Gilbert," and young fans would yell "Go, Go, Go," whenever Gilbert reached base. A teammate, future major league catcher Rick Demsey, started calling Gilbert "Go Go," and the nickname stuck.
It fit then, and has fit throughout Dennis Gilbert’s life.
