All gamblers learn something sooner or later. No matter how well you hone your game, sometimes it’s just better to be lucky than good.

Wise guy gambler Ruby Goldstein, who died recently at age 80 after a long tenure as a member of what was once known as the “sporting crowd,” was pretty damn good -- and occasionally very lucky.

He spent his life chasing the numbers and gambling on just about anything that moved. Ball games and boxing matches, horse races and other men’s poker hands, he found it hard to get out of bed before noon without having a bet down.

At one time, his name surely conjured images of another Ruby Goldstein of that generation, a tough-as-barb wire Lower East Side lightweight known as the “Jewel of the Ghetto.” The other Goldstein eventually hung up the gloves and became a referee. The Las Vegas Goldstein, well, let’s just say he had an aversion to authority.

The gambling Goldstein would make a score and spend it, catch a break and take a tumble. Along with future Black Book members Marty Kane and Joey Boston, Goldstein lived in Las Vegas during the time in its history when being a close associate of Frank “Lefty” Rosenthal was a feather in a bookmaker’s cap. Goldstein stayed around long enough to get that cap knocked in the dirt.       Associates of Rosenthal, almost without exception, eventually found themselves punching a clock in the penitentiary or members of Nevada’s Black Book of persons banned from setting foot in a casino.

Goldstein jousted with law enforcement and served his share of prison time. He’s a noted character in several Las Vegas investigative books and prison memoirs.

From all appearances, he didn’t seem that thrilled with the idea of living a square life. He consistently took pinches because he was consistently on the wrong side of the law that made bookmaking a felony offense punishable by a prison sentence. Like his associates Kane, Boston and Frank Masterana, Goldstein understood the price of doing business on the street.

No matter how good you are, the luck only lasts so long.

Former Las Vegas mayor and mob lawyer Oscar Goodman remembers Goldstein fondly and recalls the time in the early 1970s he represented him in a bookmaking case headquartered in Las Vegas but prosecuted in Los Angeles. It was back at a time the use of court-authorized wiretaps was uncommon and controversial. When cantankerous U.S. District Judge Harry Pregerson learned of the amount of money the FBI spent listening to illegal bookmakers, he went ballistic and made the defendants an offer they couldn’t refuse.

“All the clients were called in and told, ‘Plead guilty right now and no one is going to jail,’” Goodman recalls. And they did.

It was a lucky break, one that wouldn’t come along often. The deal failed to turn Goldstein into a librarian. He went right on hustling.

For a short time the Vegas Goldstein held a legitimate job, at least on paper, as the manager of the Fremont sports book downtown. The luck didn’t last.

“They gave him the Fremont book, but he blew it,” longtime Las Vegas sports bettor Lem Banker remembers. Goldstein was one of the gambling fraternity’s insiders and was liked well enough, Banker said, but he was seen with all the wrong people. And Goldstein’s shadowy friends, constantly under police surveillance, wouldn’t have dreamed of doing anything legitimate.

Kane and Boston were behind the counter of the Stardust sports book in those days and were immediately suspected of pilfering the cash register. Hemingway didn’t rewrite his short stories as often as those two edited the sports book’s betting slips. It’s always been easier to win if you punch a time on a ticket before the event and then fill in the winner afterward.

Sooner or later, of course, someone notices such things. The authorities busted out the Stardust sports book on the way to cleaning out an Outfit skimming operation.

Goldstein was tight with Rosenthal, and Ruby’s luck held as long as Lefty had the juice. That juice ran dry one October night in 1982.

Rosenthal, Goldstein, Kane, and Steve Green had just finished eating dinner at Tony Roma’s restaurant on East Sahara Ave. and were heading to the parking lot. Goldstein remained in the popular rib joint to pay the check, as the story goes, and the next thing he heard was the roaring explosion of a bomb going off under Rosenthal’s Cadillac.

The car was outfitted with an iron plate installed for just such an occasion. (Rosenthal understood life’s odds better than most and preferred preparation to luck.)

Rosenthal suffered cuts and bruises and had his new hair implants singed, but was otherwise unharmed. The other fellows were wise enough to have driven to dinner in their own cars. Goldstein was in the restaurant instead of riding shotgun with Rosenthal.

Authorities were quick to blame Rosenthal’s volatile Chicago Outfit shadow Anthony Spilotro, but the blast was more likely the work of Midwestern mob bosses who were growing anxious about the egotistical Lefty’s lightning-rod personality.

 Rosenthal recovered and got the message. In a few years, the Chicago mob’s Las Vegas days would be over. A few years more, and Goodman had reinvented himself as a popular local politician.

Years passed, and Goldstein was sometimes spotted with friends at Bagelmania. He was rumored to have made friends in the Caribbean, a haven for illegal bookmakers.

Win or lose a bet, he’d already enjoyed the luckiest night of his life back in 1982. He picked up the check, and outlived most of his friends and enemies.

On the street, that made him a lucky man, indeed.

John L. Smith is a longtime Las Vegas journalist and author. Contact him at [email protected]. On twitter: @jlnevadasmith.

Feature photo: “No more bets” by KATH is licensed under CC BY 2.0