The Gambler

"If you say that I am a gambler, you will be right. But I am an uncommon gambler. An uncommon gambler is a man who accommodates common gamblers."

Frank Costello to newspaperman Bob Considine

I once read an interview with Keith Richards where he explained he didn’t have a drug problem. He had access to, and could afford all of the drugs he wanted, so where was the problem? I view Costello’s considerable gambling habits in much the same way. He was a man who had a suitcase containing one million in cash stashed away in case of emergencies. Money was not an issue, so out of respect for the boss, let’s call his gambling a passion, not a problem. He bet big, and loved the element of risk that was involved. I believe this is what made him a successful business man, but also a successful criminal.

“I always gotta’ have some action.” he declared.

Upon entering his living room, one of the first things guests would notice was a slot machine. Frank would give each guests a nickel to play, and the machine would always pay out. When his guests handed back their winnings, he would refuse the gesture saying,

“What do I look like, some kind of punk? Nobody loses in my house.”

The next thing they noticed were several televisions, each tuned to a different game. Then the radio, probably tuned to a fight. Frank would keep track of all of these, having thousands of dollars at stake on each, as well as his constant chain of phone calls concerning the “action” he had going at numerous tracks at any given time.


His favorite thing to bet on was a special boxing match promoters would put on after the main event in what was then the mafia’s favorite retreat, Hot Springs, Arkansas. Five blindfolded men would enter the ring and punch it out until only one man was left standing. Frank loved the unpredictable nature of this bout and felt a certain sense of pride when he picked a winner. Nothing was off-limits when gambling was concerned, and he was also known to bet on such trivial things as where the first snow flakes would fall in the city.


Middleweight champion Sugar Ray Robinson sits across from Frank Costello and Genovese powerhouse Mike Miranda; ringside at Madison Square Garden, September 26, 1951.

Frank Costello and bookmaker Frank Erickson take in a fight, Madison Square Garden, May 16, 1967. Photograph by John Duprey.

When Costello went to the track (which was often), he carried his gambling money in one pocket, and his lending money in the other. If someone borrowed money from him, he always slipped in an extra one hundred dollar bill, then waited to see if the borrower brought it to his attention. If they did, they went up a notch in the boss’s opinion, if not, Frank figured he had learned a lesson cheap. 


For a brief period his pockets were not so deep. He had been tipped off that the cops were going to plant evidence on him so he had his tailor sew them up!

Most of his friends shared a similar, unpleasant experience when joining Costello at the track. This usually only happened once, as most of them were smart enough to learn their lesson.

People assumed Frank always had some inside knowledge on a race, so they would put down a heap of cash right alongside him. Costello, however, didn’t want the inside scoop. He was after all, a gambler, and wanted to win on his own accord. As a result, many of his friends suffered huge losses right along side him.

Frank Costello's horse "Palestral" in the winners circle, July 1974, one year after his death. Photograph courtesy of Gangland Legends.

His lawyer, George Wolfe, recalled one incident where Frank encountered another gambler at the Belmont race track. Frank was sure he had a winner, and suggested the man bet with him but he too insisted he had a winner and the two agreed to wager on the race. No sum had been decided on, and minutes before the event Frank turned to the gambler, sitting in his box some distance away.

Costello held up two fingers and the gambler nodded his head in agreement. Frank’s horse came out on top and he later joined the man to collect his winnings. The man pulled pulled two dollars from his wallet and handed them to a very unamused Costello. “It was two thousand!” Frank demanded, but the astonished man refused to pay. The boss had to be pulled away by friends, but not before accusing him of being a “welsher,” the worst thing you could be in Frank’s eyes. The mob boss was later asked not to return to the track.


Being banned from establishments became increasingly common for Costello as his notoriety grew.

He was asked to not come back to the Biltmore steam baths by the manager, when some of the customers had complained that a character like Frank was allowed to frequent the spa. Costello politely left, but received a frantic phone call from the manager the following day.

It seemed the entire staff had failed to show up for work and would, “Mr. Costello please come back?”


Golf was another passion of Frank’s. He often played with Babe Ruth, who was constantly borrowing money in an effort to solve his continual financial woes. During one round, Ruth asked for five thousand dollars, but Costello was hesitant to lend him the money, knowing he would never see it again. He suggested they bet the cash on the next hole, figuring Babe, the much better golfer, would win the money anyway. Frank made his first ever birdie and won. He still lent the five thousand to Ruth, but never saw it again.

The Prime Minister’s name became so synonymous with all things gambling, later in his retirement, the Yugoslavian government approached him to take charge of plans they had to build a Vegas style casino/resort. To everyone’s astonishment, Costello turned the offer down flat. “You can’t trust a government.” he explained. “One day the army might come in and take over. Then, not only are you out of business, you become part of the killing.” He recommended Meyer Lansky, stating he would be perfect for such a job.


Many believe the reason he turned the offer down was the agreement he had made with Don Vitone. In exchange for his life, Frank would retire for good.

After getting Teamster leader Jimmy Hoffa acquitted in court, lawyer Ed Williams complained to Costello who was both his friend and client. "I told you he was no gentleman.' Costello reminded him. The Mob Boss was pleased however; 


He had bet $1,000 at a hundred to one odds on an acquittal and used his $100,000 to pay his own legal fee to Williams.

Ever the boxing fan, here is Frank once again ringside at the Garden. Photograph John Duprey.

"Now they're running at Belmont because that was the track. They get the first call, and the horse they bet on is nowhere. Now everybody is angry looking. I'm standing studying all this. You could read their thoughts in their faces. Another stiff and everybody is thinking of killing the trainer or the jockey or whoever the hell gave them the tip. At the half mile pole, their horse gets a call-he's third. You could see a few smiles. Now they're at the three-quarter mark and he's second and moving up. Everybody gets up and starts to scream. They're screaming and yelling in Italian and whipping him home. So I start screaming and yelling in Italian and whipping too. He wins it by half a length, and now the dance goes on. Everybody singing, laughing, yelling. Just like 'The Godfather'-da-da-da-da-evrybody's dancing around the table. I'm dancing, Frank is giving me money, Willie Moore (Moretti) is giving me money. Johnny Caboose, Willie Moore's right hand is giving me money..."

Mickey "Cheesebox" Callahan, who Frank employed to sweep for wiretaps.

Finally we get to what had to be Costello’s strangest gambling habit of all.

Apparently, Frank was the champion at maintaining the longest, continual urine stream. He bet, and won, thousands of dollars proving it. I once visited Frank’s old haunt, the Waldorf Astoria in New York City. While using the restroom in the lobby I couldn’t get that story out of my head, for he had probably made wagers in that very restroom at one time. Fortunately I was alone, as I began to chuckle to myself recalling my favorite all time Costello quote:

“Most men I know, pissed away their fortunes. I’m the only one I know, that made a fortune pissin’.”

Background from the November 28, 1949 Time Magazine