Big Seymour Siskind: The Jewish Mobster Who Thrived as a Master Trickster

A devout lifelong criminal and hoodlum, Seymour Siskind was already committing crimes by the time he was a young teenager. He had originally started out as a burglar and sneak thief .

As the years passed, he graduated to policy numbers and bookmaking rackets as well. But his first love, his lifelong love, was stealing anything and everything worthwhile that he could get his hands on…and he simply excelled at it.

Seymour Siskind - aka “Seymour Siskin,” “Big Seymour” and “Sy the Jew” - was born in Brooklyn around 1913. During his early years, he generally resided in either Kings County or Manhattan. For many years, he listed his home address as 1478 E. 28th Street in Brooklyn.

Seymour Siskind

By the 1960s, he had relocated himself a bit further east to the Forest Hills and Jackson Heights sections of Queens County. This was another area rife with fellow Jewish hoods. For instance, during one particular arrest in 1968, he told the police he lived at 52-50 70th Street in Jackson Heights.

A Devout Criminal and Hoodlum

A devout lifelong criminal and hoodlum, Seymour Siskind was already committing crimes by the time he was a young teenager. He had originally started out as a burglar and sneak thief.

As the years passed, he graduated to policy numbers and bookmaking rackets as well. But his first love, his lifelong love, was stealing anything and everything worthwhile that he could get his hands on…and he simply excelled at it.

He fell in early on with other young Jewish hoodlums from Brooklyn who had gravitated to the notorious Brownsville-based Jewish underworld then operating under the auspices of Murder Inc. Seymour would later number several of these men among his lifelong friends and criminal partners.

Criminal Associates

The following known criminals were named as being among his closer associates.

They included top Jewish hoodlums and convicted burglars and thieves such as Maxwell (Little Max) Tannenbaum, Nathan (Nat) Heller, Joseph Ganz, Hyman (Little Hymie) Rosen, Maxwell Berner, Max Kamin, and his son Stuart Kamin, Jacob (Jack Mace) Maislich, Michael Parker, and a notorious Chicago hoodlum named Barney Auld.

<img src="https://thenewyorkmafia.com/wp-content/uploads/2020/06/siskind-bio-Seymour-Siskind-far-right-is-caught-by-news-cameras-with-rogue-detective-Jimmy-Fox-Max-Berner-and-Joe-Ganz.-All-were-arrested-in-a-long-running-theft-and-confidence-racket-ring.-1024x512.jpg" alt="Seymour Siskind (far right) is caught by news cameras with rogue detective Jimmy Fox, Max Berner, and Joe Ganz. All were arrested in a long-running theft and confidence racket ring." class="wp-image-62021" style="width:768px;height:384px" width="768" height="384"/> Seymour Siskind (far right) is caught by news cameras with rogue detective Jimmy Fox, Max Berner, and Joe Ganz. All were arrested in a long-running theft and confidence racket ring.

Although during his underworld career Siskind was known for typically operating with his Jewish brethren as racket partners, he did have at least several known direct connections to the Italian mob.

In 1960, a documented “soldier” of the Vito Genovese family named James (Jimmy Bates) Battaglia was nabbed along with Siskind and others in an elaborate “bust out” racket the men were operating. Several years after that he was also tied to a very notorious Genovese family power named Salvatore (Sally Burns) Granello. More will be discussed about them below.

Siskind and his gang were also known for collaborating with corrupt New York City Policemen over the years to further their criminal activities accordingly.

A Master Burglar and Thief

Big Seymour Siskind was an extremely larcenous hoodlum to his core. No scam or theft was beneath or above his dignity or ability. By the time Seymour came of age as a young criminal, he was already expanding into major thefts and heists.

Nobody knows exactly where or when he gained his vast knowledge of security locks and how to pick them, but the New York City Police Department once labeled Siskind the “number one premier burglar” of high-end valuables in The Big Apple. By the 1950s, the Miami Metropolitan Police Department of Dade County felt the exact same way.

In 1952, then New York City Police Commissioner Monaghan even went one step further when he labeled Siskind “the best lock-picker in the United States.”

Siskind was well known for “burglarizing” high-rise luxury apartments and swank hotels in Midtown Manhattan and in Brooklyn with his criminal cronies. But he wasn’t just some random thief.

Siskind is frisked by a detective while another plainclothes detective looks on.

He and his burglary gang would carefully target their victims beforehand, usually selecting top-level executives of various blue-chip companies or multimillionaire business owners for these thefts.

They usually sought out expensive jewelry, diamonds, gold, and other precious metals such as sterling silver, furs, cold cash, negotiable stock certificates, bearer bonds, etc, anything that could be easily “fenced” for a quick profit.

These quiet robberies often produced a plunder for his gang running into the hundreds of thousands of dollars a pop. Siskind operated in this manner for decades, quietly and efficiently often making his “earn” off the backs of unsuspecting socialites.

It's not that he was never arrested for his larcenous shenanigans. Quite the opposite, in fact. Through the years, starting from the late 1940s through at least the 1970s, Siskind was picked up by the authorities many times.

Thick Enough to Choke a Horse

He had an arrest record with the NYCPD a mile long. He also had a criminal record of arrests in Upstate New York and down in South Florida as well. He may have had arrests in other cities also.

The NYPD's “Safe & Loft Squad” located at 400 Broome Street in Downtown Manhattan had a file on Seymour Siskind thick enough to choke a horse.

On occasion, they also stored the various items and stolen loads he had pilfered by securing them inside their Property Clerk’s Room after having arrested him.

A burglary squad detective places Seymour Siskind under arrest and into a cop car for a ride to the lockup.

But Siskind was a very versatile hoodlum who was adept at modifying his methods and criminal activities as various opportunities presented themselves.

Over the years, he had been arrested for or connected to such rackets as ticket-scalping, horse and sports bookmaking, con games, extortion and blackmail, police bribery, criminally receiving and then “fencing” stolen goods back into mainstream commerce for other thieves, stock thefts and frauds, and elaborate bankruptcy fraud scams.

His police “yellow jacket” listed numerous arrests:

>> burglary (thrice) >> attempted burglary (twice) >> possession of burglar tools (twice) >> robbery >> ticket-scalping (twice) >> grand larceny (twice) >> possession of stolen property (thrice, six months on one conviction, one year on another) >> criminal conspiracy >> vagrancy >> violations of NYS traffic laws (6 days in jail) >> forgery and possessing forged papers >> petty larceny >> unlawful entry >> criminally receiving >> bankruptcy fraud and conspiracy >> attempted extortion and conspiracy (3 years in state prison) >> consorting with known criminals >> criminal possession of stolen securities

...and more

He was a notorious criminal among New York law enforcement and later with the FBI as well.

Bookmaking and Ticket Scalping

In the early 1950s, after a three-day investigation by the New York Police Department, Siskind was among seven Brooklyn men arrested for operating an elaborate illicit ticket-scalping business they were running out of Midtown Manhattan. The police had conducted physical surveillance and placed several court-ordered telephone wiretaps on the suspects.

Cracking down on what they described as an organization of “ticket speculating,” police authorities of Manhattan’s Third Division raided three business establishments.

Named as the nerve center of the racket was the Central Ticket Agency, 254 West 49th Street, where an undercover policeman had made repeated “buys,” including purchasing two $10 tickets for a fight at Madison Square Garden for $25 each.

<img src="https://thenewyorkmafia.com/wp-content/uploads/2020/06/siskind-bio-Seymour-Siskind-far-right-is-caught-by-news-cameras-with-rogue-detective-Jimmy-Fox-Max-Berner-and-Joe-Ganz.-All-were-arrested-in-a-long-running-theft-and-confidence-racket-ring.-1024x512.png" alt="Seymour Siskind (far right) is caught by news cameras with rogue detective Jimmy Fox, Max Berner, and Joe Ganz. All were arrested in a long-running theft and confidence racket ring." class="wp-image-62022" style="width:768px;height:384px" width="768" height="384"/> Seymour Siskind (far right) is caught by news cameras with rogue detective Jimmy Fox, Max Berner, and Joe Ganz. All were arrested in a long-running theft and confidence racket ring.

Taken into custody inside the ticket office raid were thirty-three-year-old Seymour Siskind and twenty-six-year-old Samuel Stewart. They were both charged with criminal conspiracy and illegal ticket-sale charges.

Police then raided an eight-floor apartment at 100 West 55th Street and arrested their accomplice Samuel Berger. The forty-two-year-old Berger was charged with the same criminal counts.

A Hotel Gambling Den

Next, a team of plainclothes detectives raided an affiliated gambling ring operating from the second-floor of the Hotel Markwell, located at 220 West 49th Street, directly around the corner from the ticket agency. The detectives arrested four more men who were identified as Bernard Brown (34), Harold Raymond (43), Abraham Diamond (32), and Michael (Mickey Jordan) Giorano (39).

Each suspect was charged with bookmaking and released on bail ranging from $500 to $1000 each. The gamblers were accused of accepting wagers on various Garden events and on horse races.

A seventh suspect, fifty-seven-year-old Sigmond (Sid) Silver, was also picked up inside Madison Square Garden and charged in this probe. All seven men arrested were later arraigned in Gamblers Court.

After he relocated down to Florida, Siskind’s codefendant Michael Giorano was later identified by the Miami Beach Police Department as one of the more active mob-connected bookmakers then operating in Dade County. They said that Giorano was believed connected to the Genovese crime family.

The Casino Scheme

By the mid-late 1960s, the FBI was taking a closer look at Seymour Siskind. Field Agents were starting to see Siskind show up on their radar screen more often during investigations of other known hoodlums, especially mafiosi.

Over the next few years, Siskind was tied to several major crime figures not the least of whom was Genovese family member Salvatore (Sally Burns) Granello. Granello was a notorious hoodlum from the Mulberry Street area of New York’s Little Italy neighborhood and one of the most active racketeers in the country.

In September 1970, while the FBI was conducting a deep probe of this versatile mafioso, the U.S. Assistant Attorney for the Southern District of New York tied Granello and Siskind to an attempted plot to purchase a gambling casino in San Juan, Puerto Rico, on behalf of the underworld.

To San Juan and Back

Under federal subpoena, a wealthy New Jersey industrialist named Thomas Granatell testified before a Federal Grand Jury that Granello was indeed currently employed by his company, Swing-A-Knit. The NYC garment firm then owned by Granatell.

Granatell subsequently also submitted to the AUSA a sworn letter requesting Granello be allowed to travel back and forth to both Miami and San Juan in furtherance of his garment business and a proposed casino venture. At that time, Granello was under indictment and under the terms of his bail package was generally being restricted from traveling outside New York’s Southern District.

Tom Granatell admitted that he was financially backing Granello in this purported gambling venture. Several months earlier in July of that same year, “Sally Burns” and Seymour Siskind had been tracked by federal agents boarding a flight en route to San Juan.

The pair were traveling to San Juan for business meetings to negotiate the purchase of the casino.

Complex Gambling Endeavors

During the late 1950s and 1960s era, authorities had connected Sally Granello to the operation of several lucrative off-shore casinos the Mafia operated in such places as Haiti; Nassau, Bahamas; and other Caribbean islands.

Granello was said to be very adept and trusted by his underworld associates at understanding the functions and machinations of these sorts of complex gambling endeavors.

On August 25, 1970, the San Juan office of the FBI advised their New York counterparts that Granello had arrived that day via Pam Am Flight #459 from Miami, Florida. Granello was in the company of one Seymour Siskind, a known hoodlum from New York.

Agents further advised that both Granello and Siskind checked into the Americana Hotel with the mafioso assigned Room #1506 and his Jewish partner in crime assigned the next suite over, Room #1508.

Over the next several days, federal agents watched as the two New York hoodlums made contact with J.J. Otero, the registered owner of both the El Miramar Hotel & Casino and Le Petite Hotel & Casino in Condado, Puerto Rico. Both hotels were closed at that time due to financial problems.

Granello and Siskind met Otero that same evening to discuss the possible purchase or long-term lease of the Le Petite Casino to reopen the gambling operation. Two days later on August 27, they departed San Juan on a flight back to Miami Airport.

A close aide and hoodlum associate of Granello’s named Dino Conte was observed meeting the two men at the airport on their return to Miami.

Somebody's Talkin'

Side Note: On September 2, 1970, a New York-based FBI informant operating under the code name NY T-2 told his federal handlers this:

“There were two hotels in San Juan, namely the Le Petite and the El Miramar, which were reportedly available on a lease basis. Seymour Siskind was primarily interested in the gambling casinos which were a part of the hotels.

Source learned through an individual named Gabe Canavas, who was a former assemblyman in San Juan, that the owners of these hotels were in financial difficulties and unable to meet their payrolls. Upon learning of these problems, Siskind approached Sally Granello to try and obtain the heavy financial backing required through a multimillionaire businessman named Thomas Granatell whom the mafioso was closely connected to.”

The two hoods were said to have traveled to Puerto Rico at Granatell’s expense to try and pursue the deal. The Le Petite was said to be a 96-room hotel, and the El Miramar was a 216 room hotel. The lease for the Le Petite called for $240,000 if the deal was consummated.

In addition, the informant stated that another $24,000 was required to purchase a government-issued license to operate the casino. Another $25,000 bankroll and a revolving $17,000 per month to meet payroll were also needed.

Nothing would ever materialize regarding the casino deal, but it served to help the feds understand Siskind’s mob connections and his place within the New York underworld’s hierarchy and pecking system.

A Stool Pigeon Surprise

Important Side Note: In 1970, an internal FBI #302 report which is required to be furnished by all field agents to FBI Headquarters in Washington, D.C. on a monthly basis confirmed that, in fact, informant NY T-2 was actually Seymour Siskind.

It is not known exactly why he decided to cooperate or when he was converted into a federal informer. But official FBI internal reports do confirm his steady cooperation by at least that point in time.

To protect his identity, Siskind was also assigned a dual Informant code number, NY-7446. This particular report documents that Siskind was providing the FBI with key evidence against his supposed buddy Salvatore Granello.

Tracking NY T-2 shows that he was instrumental in confirming the identities of numerous mob figures in all five New York crime families through the years for law enforcement.

His informant code number is placed next to the names of literally hundreds of mafiosi in #302 field reports submitted to FBI headquarters. So, it seems, he was both a prolific thief - and a prolific rat - all at the same time during his long criminal career.

The same report goes on to mention that because Genovese family bosses had approved the murder of Granellos’ son Michael, who was slain back in 1968, the FBI felt that a bitter Granello was himself a possible prime candidate for future FBI informant development tactics.

Both Hands in the Cookie Jar

Dating back to the 1940s and early 1950s, Siskind had participated in many other types of confidence schemes and swindles in towns and cities all along the eastern seaboard.

For instance, in 1949 in Upstate New York, he was once the “victim” of an alleged “armed robbery” by two men while he was up visiting Saratoga Race Track for some alleged leisurely horse-race betting.

He and two friends of his, convicted criminals Hyman Rosen and Max Tannenbaum, reported to the Saratoga County Police Department that they had been jumped by several unknown men.

They reported that the men robbed them after being accosted by gunmen in the parking lot of Smith’s Interlaken, a popular local nightclub located just 5 miles from the Saratoga Race Track.

The armed men allegedly shoved the victims into Siskind’s automobile and made them drive toward the racetrack at gunpoint while they were relieved of a $1,000 diamond ring and another $6,000 in cash they claimed to have had with them at the time.

(I suspect this claim was r eported to local authorities so that there would be an official police report so the conmen could later file fraudulent claims with insurance companies.)

On another occasion, Siskind was picked for attempted burglary after police in Baltimore, Maryland, arrested him and several accomplices mid-stream after they were about to gain entry inside a Baltimore City apartment. They were caught red-handed inside the high-rise residence looting it of valuables. In their possession were numerous burglars' tools.

Siskind was also picked up on similar charges in Miami Beach one winter season while attempting to do ‘his thing’ outside another luxury apartment by the Miami Police Department. He was charged with loitering, possession of burglar tools, and attempted illegal entry.

The "Bust-Out" Bust

In June 1960, in what is commonly known as a “Bust Out,” Siskind was among seven men that included Genovese family soldier James (Jimmy Bates) Battaglia arrested and later indicted for operating a massive bankruptcy fraud “bust out” ring.

The ring planned to defraud numerous manufacturers and wholesale supply houses of over $400,000 in merchandise by setting up three dummy corporations that obtained the goods on 30-days credit. They then planned to resell the merchandise and dissolve the dummy firms before payment to these supply houses was due.

But their scheme was thwarted by authorities who moved in and arrested the suspects before they could actually complete the gambit.

Accused of possessing stolen merchandise, grand larceny, bankruptcy fraud, and conspiracy, besides Siskind (47) and Jimmy Battaglia (47), who was listed as the president of Big City Shipping Company of Lower Manhattan; were Martin Teplin (35), and his brother Alvin Teplin (27); William Cooper (50); Herbert Oberman (35); and Morton (Morty) Rosenberg (47).

New York City Police said the scheme began the previous February when the Teplin brothers and Cooper first established three dummy corporations in Manhattan. In April, using printed stationary on the newly formed companies, the men placed at least 151 purchase orders for merchandise from various companies and supply houses from all over the United States.

Side Note: At a news conference after the arrests, one of the lead detectives said, “We were first tipped off to the fraud operation after receiving information from an informant that Siskind, a convicted burglar, had been seen spending money freely.”

So, the detectives then set up a watch on him and discovered his connection with the dummy firms. (yeah right! lol)

Playing Cat and Mouse

Eventually, after weeks of undercover surveillance and a game of ‘cat and mouse’ between the thieves and city detectives, police raided the warehouse where the hoods had stashed over $150,000 worth of the stolen loads.

After doing a full inventory of the stolen goods recovered, the police realized that only a partial portion of the loot had been recovered. The thieves had already ‘fenced’ a good portion of the stolen merchandise.

Law enforcement had also earlier raided a storefront used by the ring where they recovered over $200,000 more in stolen items. All told, over $380,000 worth of stolen merchandise from suppliers around the country had been recovered.

It was one of the largest stolen goods rings ever broken up in New York City. Never before had that amount of pilfered items ever been recovered by the Manhattan-West Burglary Squad.

The warehouse raid was conducted after the police had already grabbed the seven hoodlums in relation to the thefts. After faking more knowledge about the gang than the police actually knew, the authorities claimed they were tipped off by one of the gang to the warehouse cache after two anonymous telephone calls were received by one of the detectives working the case.

Several days later, two keys were mailed to Detective Jerry Mullane of the Burglary Squad along with a note directing him to the address where more goods were stashed and letting him know those two keys would give him access inside the stash house.

(This might have been Siskind again providing help to the cops to try and wiggle free of his own charges.)

Duping Suppliers

Detective Mullane later told newsmen the three companies opened up for the scheme had similar-sounding names to those of accredited reputable companies which helped to dupe suppliers into offering a line of credit to buy goods in wholesale lots from these legitimate manufacturers.

The merchandise largely consisted of sporting goods such as bowling bags, baseballs and bats, fishing reels and tackle boxes, sleeping blankets, axes, hunting gear, golf tees, and with some possible sense of foreboding, even judges gavels.

The ring then ordered the manufacturers to ship the goods to stores they rented in the Bronx. The suspects would then immediately move the merchandise to other secret locations and close the original storefronts.

Ever since the first set of arrests made that June with the aid of the FBI and U.S. Postal authorities, NYC detectives pretended to know a lot more about the operation than they actually did. Through the use of wiretaps and informants, the main stash warehouse was finally raided at 597 Academy Street in the Inwood section of Upper Manhattan.

Police say the place was piled high to the ceiling with thousands of crates of merchandise. It took 12 cops nearly eight hours to load all the stolen goods into multiple large tractor-trailers to cart them away. Authorities say that at least 29 manufacturers from all over the country had been gulled into sending merchandise.

Stolen Securities

In April of 1968, Manhattan District Attorney Frank Hogan’s Office made the announcement that his detectives had arrested Siskind once again, along with three other hoodlums after they attempted to peddle a stolen $100,000 U.S. Treasury bill.

The men were seized by undercover detectives after three of them attempted to sell the Treasury note to the fourth suspect. The bill was one of fifty reported missing with an aggregate value of $1,552,000 taken from the Hayden-Stone Investments Inc., located at 80 Pine Street in Lower Manhattan.

The Kamin’s, father and son, are seen here after their arrests for attempting to “fence” stolen securities.

Besides Siskind, the others arrested were identified as Max Kamin, his son Stuart Kamin, and Michael Parker. The detectives watched as Parker handed the younger Kamin $15,000 cash in exchange for the Treasury note during a sidewalk rendezvous.

Detectives then moved in and arrested the quartet. Authorities said the bill was in a brown envelope that was addressed to a doctor in Zurich, Switzerland.

Exit Stage Left

After these particular arrests and indictments, Siskind seems to have faded off from the scene. Perhaps his time was up.

Perhaps his prior cooperation with local and federal law enforcement was finally discovered, and he was fully exposed to his underworld brethren as a stone rat which forced him to flee the New York area and other former haunts once and for all.

Maybe he was swept up into the Witness Protection Program for his safety…Maybe he died.

But whatever the case may have been, after the late-1960s period, no more was ever publicly heard from Seymour Siskind.

I attempted to track his later movements and check for his date of death but both his first and last name is so common, especially in the New York and Florida areas, that tracking him down for a positive ID was virtually impossible.

Regardless of what finally became of him, during his lifetime, Seymour (Big Seymour) Siskind was one of the most prolific thieves and confidence men in the New York and South Florida underworld.

He may have also been one of its most slippery and slimy informants!

Until next time…”The Other Guy”

Big Seymour Siskind: The Jewish Mobster Who Thrived as a Master Trickster

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Big Seymour Siskind: The Jewish Mobster Who Thrived as a Master Trickster

Unlock The Door to the Underworld

Take the Journey!

You May Also Enjoy

Chicago Outfit Tycoon – Ross Prio – Pt. 1: “Treacherous Beginnings”

Portland, Maine’s Main Mafioso – “Mickey Naples” Napolitano

Meyer Lansky – “The Mob’s Accountant”

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