Bugsy Siegel in Los Angeles Pt. II: Man About Town

Read Pt. I here.

As is now known, Benjamin “Bugsy” Siegel made a number of trips to Los Angeles in the early 1930s, often with his family in tow. This information comes not from secret gangster sources that can’t be revealed, but the plain old, dull documentary record.

In 1933, with Prohibition was coming to an end, first with the return of beer then full Repeal by the end of the year, California legalized pari-mutual betting again, and horse-racing was a big money-making industry. It was a gift to those who profited from illegal gambling also: bookmakers. According to an LAPD report complied for the State Crime Commission in 1951, the two biggest horse books in Los Angeles at the time were run by Tutor Scherer and former LAPD vice cop Guy McAfee, and that Jack Dragna muscled in on the action. The Crime Commission, organized shortly after (and largely because of) Siegel’s death in 1947, established that Siegel subsequently took over bookmaking, putting Dragna, now his subordinate, in charge the day-to-day operation.

In a 1940 affidavit asking the court for permission to leave the country on “business,” Siegel stated that he’d been a permanent resident of Los Angeles since 1935. He may have exaggerated in order to make himself appear less of a flight risk, but the claim is not inconsistent with the documentary recrod. In any case, he had definitely decided to put down roots here by October 1937.

A small item appeared in the LA Times real estate section on October 10, 1937, announcing that “Ben Siegel” was building an estate on North Delfern Drive in exclusive Holmby Hills.


Two weeks later, on October 1937, there was a second attempt on the life of gambler Les Bruneman, an associate of LA’s onetime bookmaker king Farmer Page, back in Page’s long forgotten bootlegging days. This time it was successful. Popular myth has it that Siegel, in a scene right out of a Hollywood Godfather movie, had organized all the gamblers in town and told them he was taking over. All supposedly went along with it except Bruneman. Ok. 

The Bruneman murder opened an investigation of the usual local gambling “big shots,” who scattered to the winds. At the same time, cafeteria owner and 1937 county grand jurist Clifford Clinton was wrapping up his citizen-led investigation into gambling and vice. Things came to a head in January 1938 with the attempted murder of former-PI-turned-LAPD-detective-turned-PI-again Harry Raymond in a crudely rigged car bombing, later traced back to an LAPD detective Earl Kynette, a contemporary of Raymond (and Guy McAfee). In the fallout from this scandal, LA voted to recall mayor Frank Shaw, and installed judge Fletcher Bowron in his place. Bowron set to work trying to- for real- clean up the LAPD and rid the city of vice. The “big shot” gamblers like McAfee made a huge show leaving town, and their exodus attributed to Bowron’s reform efforts.

But there were repeated hints in the press that there was a “new man” in town running gambling who was squeezing them out. After all, Bowron’s influence as mayor did not extend to unincorporated county territory, like the Sunset Strip, where McAfee, Page, and the others had run illegal gambling clubs through fronts.

Meanwhile, Siegel was ensconced in his estate at 250 North Delfern, with wife Esta, their two young daughters and a live-in staff of three (butler, cook and maid), and enjoying the life of a “Hollywood sportsman.”

The Law first came calling at 250 N. Delfern on January 19, 1939, when federal agents, acting on a tip from a man who claimed to be a former employee, raided the palatial home in search of smuggled perfume. They found nothing.

250 N. Delfern in 1940.

Law enforcement officers were again dispatched to the address in August 1940. This time the charge was murder. Siegel’s butler John Hood met them at the door. He left them waiting on the doorstep for two or three minutes, then returned and let them in. Searching the house, they discovered several secret panels, including a bookcase that pivoted, revealing a hiding place; a secret closet that contained filing cabinets; and two sliding panels that concealed safes. In one safe, detectives found canceled checks: $1k to Farmer Page $1k, $4k to Eddie Nealis, both affiliated with The Clover Club on Sunset Boulevard.

Upstairs they found a trapdoor inside a linen closet. It led to the attic where Siegel was discovered, hiding in his pajamas. (Los Angeles Times Aug 22, 1940 and Jan 31, 1942).

Delfern parlor. LAPL

The bar at Delfern, flanked by slot machines. LAPL

The pool and cabana/guest house at Delfern. LAPL

Siegel was a suspect in the gangland-style execution of eastern gangster Big Greenie in Hollywood back on November 22, 1939. While in custody, he told officers most of his income came from bets on horses.

8/22/1940 LAT

Siegel was able to beat the rap in the Big Greenie case after the corroborative witness against him, Abe Reles, went out of the window of the hotel in Coney Island New York where he was being held in protective custody.

In 1941, Nevada legalized off-track betting. Through fronts such as Moe Sedway and others, Siegel began running in Las Vegas horse betting parlors, and increasingly tried to gain control of West Coast race wire operations, state and national efforts by law enforcement to shut it down having failed.

In 1944, the Siegels decided to separate. Esta moved back to New York with the girls. Siegel put 250 N. Delfern on the market. He thereafter used his married sister and brother-in-law’s Beverly Hills address as his official residence, but lived in various rented abodes and hotels.

sunset-tower-8358 Sunset Streip-postcard view

On May 25, 1944, Siegel, whom the friendlier papers still referred to as a “sportsman,” was arrested on bookmaking charges at the Sunset Towers apartment of friend Aaron Smehoff, better known by his alias, which can be seen in the article below.

6/24/1944 LAT

Siegel in court, 1944 flanked by lawyers Max Solomon and Issac Pacht. UCLA

As Siegel was being charged with felony bookmaking, actress Loretta Young, whose husband Lt. Col Thomas Lewis, was serving overseas, bought 250 N. Delfern for $85,000, giving Siegel a down payment of $8500.

Then a pest report came back with bad news: Bugsy’s house was, well, infested with bugs. Termites, specifically. It was going to cost $350 to have them exterminated. Siegel, who contended that Young had already gotten a heck of a bargain, refused to pay. He. The best he would do was offer her a $250 credit toward the purchase price. Young wouldn’t deal and demanded her $8500 back.

Young with Alan Ladd on the set of And Now Tomorrow (1944).

On August 1, 1944, Young gave birth to a son. While she was still in the hospital, Bugsy sued her. The court decided in favor of Young in January 1945. In April 1945, 250 Delfern found a new buyer.

1/13/1945 LAT

By then, Siegel was increasingly shifting his operations to Las Vegas and the construction of the Flamingo hotel, a permanent LA resident no more. Or so he thought.


Re: Smehoff, see California Special Crime Study Commission on Organized Crime, Third Progress report, 1/31/1950.

$85,000 was about average for the neighborhood, actually. Actress Sonja Henie bought 243 Delfern (formerly home of director Norman Taurog) for a reported $90,000 in July 1943, for example. Dancers Fanchon & Marco sold a furnished 14-room Mediterranean-style home on 2.5 acres at 320 Delfern in September 1944 for $80,000.

Siegel was not too busy to appeal the 1945 decision, but in April 1946, the court again ruled in Young’s favor.

1944 for $80,000.

Siegel appealed, but in April 1946, the court again ruled in Young’s favor.


3 thoughts on “Bugsy Siegel in Los Angeles Pt. II: Man About Town

  1. We have all heard of Meyer Lansky -mafia tycoon born around 1902 died 1982Lansky, who had already had a run-in with Charles “Lucky” Luciano, saw a needed gang – first person he recruited for his gang was Siegel?Story about Virginia Hill ran away from home 17yr old to Chicago IL work restaurant World fair where she met mob guy Joseph Epstein? Epstein introduced her to Illinois mobsters Syndicate which rumors have it she lay in bed with all of them at one time or another & even Epstein told Lansky
    about Hill?Frank Nitti-Rocco Fischetti-Tony Accardo -Joe Adonis & Ben Bugsy Siegel to name a few?Virginia Hill mob mistress mole that bag Courier for mob (Frank Sinatra worked as a mafia courier and was nearly caught carrying a suitcase stuffed with $3.5m, according to the entertainer Jerry Lewis.)Hill supposedly never short changed the mob?Anyway,Virginia Hill have a hot romance with Bugsy Siegel which Siegel named his casino hotel after her nickname he called her Flamingo.But the casion was take much longer then expected and cost more than it was figured at the time in Nevada Las vegas desert which made mob upset think Siegel was skimming /cheat out of money?Siegel was excessively spending Mafia money, and after being warned many times by Meyer Lansky.On day that Siegel diedJun20,1947 ,Supposedly virginia Hill was in Europe -that MeyerLansky met her there to ask her to give him the money which supposedly she did ?(Hill died of an overdose of sleeping pills in Koppl, near Salzburg, Austria on March 24, 1966 at the age of 49.)
    One of her brothers, Chick Hill, had been at the house in Beverly Hills when Siegel was killed. In 1966, Virginia Hill died of an overdose of sleeping pills in Austria. She was 49.Rumor has it ,Hill’s family were involved in the situation. Sindler says he saw “Virginia Hill and her military brother in front of the Flamingo, arguing about Siegel beating her up” and that he “heard Virginia Hill’s brother say he was going to kill Siegel.”(footnote:Meyer Lansky and his daughter Sandra had dinner with Willie Moretti the night before he was slain/another Relative said he-Lansky went ride Las Vegas to investigate Siegel /Flamingo Hotel?According Stacher, Mathew “Moose” Pandza, would murder Siegel( lover of Sedway’s wife Bee, )for threatening Sedway’s life /Siegel wanted Sedway killed for reporting all the finances to Lansky&Moose later married Bee after Sedway died of multiple heart attacks in 1952?On jun20,1947Rumor has it ate at the JackBeach Ocean Park -then Notorious Gangster Allen Smiley sat next to Siegel on couch front of windowVirginia Hill’s Beverly Hills home, just south of Sunset Boulevard, Linden Drive& Smiley duck to the floor for cover while shots hit Bugsy2in eye’s ? Andy Edmonds Stated Smiley disappear in kitchen?
    -mobster, Alan Smiley-Upstairs, Chick Hill, Virginia’s brother, was romancing his girlfriend, Jerry Mason-
    after theSiegel hit, Lansky’s associates,David Berman including Gus Greenbaum and Moe Sedway, walked into theFlamingo and took control of the hotel.Jerri Mason (left) and Chick Hill (Virginia Hill’s brother) at Bugsy Siegel’s inquest June 25, 1947?Means Motive Opportunity payoff /benefit ?


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