They don’t make them like this anymore
“Sailor Roberts’ two most favorite things in the world were women and drugs,” explained poker historian Johnny Hughes. “Both contributed to his downfall.”
Too many kids today try to emulate the baller lifestyle, but Sailor Roberts was the original baller. If Sailor had his own beer commercial, he’d be the guy who busted Dos Equis’ “Most Interesting Man in the World” in a card game and then stole all his women. Sailor epitomized old-school cool. He was a man’s man, and lived during a time when real men rolled their own cigarettes and casually referred to women as “broads.”
Sailor Roberts was a throwback to a time when anti-heroes were beloved and adored in an era dominated by Norman Rockwell’s picture-perfect landscape of post-war America. Sailor is the closest thing poker has to Don Draper, the whiskey-guzzling womanizer from the hit TV show “Mad Men.” Sailor would be vilified in today’s PC-driven modern times, when anything slightly controversial is scoffed upon. Too bad Sailor didn’t have a Twitter feed when he was living hard on the road in the 1960s because his Instagram galleries would be filled with pyramids of cash and blurry muff shots from random girls he picked up that afternoon.
If you look up Sailor Roberts’ statistics on different poker databases, you’ll find a few innocuous stats. Brian ‘Sailor’ Roberts won his first World Series of Poker bracelet in May 1974 when he took down the $5,000 NL Deuce to Seven title. Crandell Addington finished third in that event, and Sailor beat Larry Perkins heads-up for the championship. The next spring, Sailor won the 1975 WSOP Main Event, back when it was a “winner take all” format. Sailor earned $220,000 that night after successfully beating Bob Hooks heads-up for the bracelet. Depending on who you talk to, Sailor blew the majority of his winnings on his favorite vices — women and drugs.
In 1982 during the twilight of his career, Sailor made another remarkable run at Binion’s, but came up short. Sailor final tabled the Main Event that was eventually won by Jack “Tree Top” Strauss. For an eighth-place finish, Sailor essentially doubled up his $10,000 buy-in.
In a short recordable career, Sailor netted roughly $260,000 in career tournament earnings, although he supposedly racked up a couple of million in side games during a time when a million dollars actually meant something. Sailor’s minimalist stats are one-dimensional and barely scratch the surface of his legend and legacy. They’re a poor indicator of his overall skill at the poker table, nor do they demonstrate how he was one of the pioneers of professional poker as one of the original Texas Rounders. Somewhere in between lies the man behind the myth, which is why you’ll hear mostly gossip and half-truths about the latter stages of Sailor’s life. Most of what I grokked from the various stories I heard was that Sailor had become the personification of a downtrodden and self-indulgent gambler who had everything but pissed it all away embracing the Dionysian lifestyle.
First of all, let’s talk about Sailor’s nickname. Today’s pros are most known by their online screen names: Durrrr, Timex, and Isildur. Back in the ’50s and ’60s, grizzly card slingers had unique nicknames like Puggy, Amarillo Slim, Cadillac Jack, and Texas Dolly. Granted, Sailor’s nickname wasn’t extremely inventive. He had served in the Navy during the Korean War and had just gotten back to the States when he embarked on his career as a card player. His given name, Brian, seemed too pedestrian for the fringe lifestyle, so he embraced the obvious “Sailor” moniker bestowed upon him by the regulars in an underground game in San Angelo, Texas. “Sailor” gave Roberts a grittier edge.
“Don’t fuck with Sailor. Those Navy guys are crazy.”
Doyle Brunson once said that Sailor could have been the greatest card player of all time if it weren’t for his favorite pastimes — drugs and women. Brunson looked up to Sailor as his mentor, not just in poker, but in life. In Brunson’s autobiography, “The Godfather of Poker,” he told numerous stories involving the early days of the exceedingly dangerous, yet highly profitable Texas Circuit. Brunson and Sailor originally crossed paths in Fort Worth, where the two frequented a high-stakes game at the Diane Hotel, which doubled as a flophouse and part-time bordello.
The majority of Brunson’s Texas Circuit stories began with “Sailor, Slim, and I….” The triumvirate of Amarillo Slim, Sailor Roberts, and Doyle Brunson were partners and played out of a pooled bankroll. Those three were always getting themselves caught up in hijinks. Even when they weren’t looking for trouble, trouble found them like an unlucky, incorrigible deadbeat from a Johnny Cash song.
“Dull moments never existed,” wrote Brunson. “They were the two most colorful guys I ever met.”
The three became a Texas version of the Three Musketeers. Due to the occupational hazard of being a professional rounder, they often played in games on the “other side of the tracks” and always watched each other’s backs. They never knew if the game was going to get jacked by robbers or busted up by local law enforcement. They once played a game in Oklahoma that hired a machine gunner to sit on the roof as a deterrent to would-be thieves.
One of my favorite stories about Sailor Roberts the degenerate was the time one of their card games on Exchange Street in Fort Worth was raided. The cops entered the joint in the middle of a hand of Kansas City Lowball. Sailor asked the cops to let them finish the hand, which they surprisingly agreed to do. Sailor dealt the remainder of the hand and actually won the pot.
“I haven’t made a hand all night and then you guys pick this time to come barging in,” he bemoaned.
Of course, real cops wouldn’t have allowed Sailor to continue gambling. The group who raided the game was actually a gang of thieves cleverly dressed up as cops. They tied up all of the players and stole all of their money, watches, and jewelry.
Another one of my favorite stories involved the first time Brunson, Slim, and Sailor played Keno. This was the early 1960s during a trip to Vegas to play cards at the Golden Nugget. They were bored until Brunson’s curiosity for Keno gave them something else to help pass the time. The Texas boys had had never played Keno before, and one of Brunson’s friends described it as a crappy house game, which had the lowest odds in all of Vegas. Nevertheless, Brunson and his buddies bought half of a Keno ticket. They hit all eight numbers and won $25,000. They headed back to Texas with their jackpot, which they used to bankroll a bookmaking operation. Despite making a generous income as bookies, Sailor always blew his windfall on women, booze, and fast cars. But luckily, Brunson was there to bail him out of trouble.
Even though everyone knew about Sailor’s weaknesses for debilitating vices, Sailor always had Brunson to help get him back on his feet. These days, the self-righteous hard-asses on “Intervention” would single out Brunson as an enabler, but he was doing what best friends do — pick up your pals when they fall. As time grew on, Sailor fell harder and harder. It’s a testament to Brunson’s loyalty that he put up with Sailor’s antics for as long as he did. But sometimes that old adage fits, “You can’t teach an old dog new tricks.”
Speaking of dogs, Brunson once won Sailor’s dog. It happened in San Angelo, where Brunson and Sailor golfed for nine holes on a local municipal course. Sailor was down, so Brunson agreed to play the back nine to give him a chance to win some of it back. Unfortunately, when they finished up, Sailor was stuck almost $2,000. He didn’t have a cent to his name, so Brunson decided to take the only thing of value Sailor owned — his German shepherd named Flirty.
“If you can’t pay up, I’ll take your dog. He likes me better than you anyway,” said Brunson.
In addition to being a bookie, golf hustler, and poker player, Sailor was also an underrated contract bridge player. Although it was just one of his hobbies, his peers regarded him as one of the best bridge players around. Sailor loved to hustle out on the golf course which he had been around ever since he was a little kid growing up in San Angelo. Sailor looped at one of the local country clubs, which is where he got his first taste for gambling by shooting dice with the other caddies. During his two tours in Korea, Sailor routinely played poker and shot dice during his downtime. Upon his return to Texas after the war, he didn’t think twice about playing professionally. He eventually crossed paths with Brunson in Fort Worth, and the rest is history.
It was surprising that Sailor lived as long as he did. Along with Brunson and Slim, they all flirted with danger during the circuit days when you never knew if you were going to get hit by robbers or busted by cops. Living in Las Vegas for too long will drive anyone crazy. Sin City’s incredulous gambling gods have destroyed many a man’s soul, especially if you have proclivities to hard drugs and tempestuous women. But despite all of his defeats and setbacks — busto to robusto and busto again — Sailor survived the rough-and-tumble Texas circuit and vigorously raged in Vegas during epic multiple-day benders, before finally succumbing to sclerosis, which was brought on by hepatitis, a malingering souvenir he acquired from living life too hard and too close to the edge.
“Cocaine and heroin did him in,” explained Johnny Hughes. “Those drugs took ahold of him and he became a shell of his former self. It’s sad because everyone loved Sailor. Everyone. He also had the best women on his arm. He always had the most fun. Sailor was the life of the party.”