Although Milwaukee’s Mafia family had multiple ties to Florida through Universal Builders, the Fazio brothers and Chicago’s many Miami outposts, we are going to look at a lesser known figure, Bobby Pick.
Bobby Pick
Bobby Pick, born in Milwaukee on January 10, 1914 as Robert George Pick, grew up under the tutelage of his father, Sam William Pick. Sam, in turn, had come up in the business as a tavern manager for Robert Lawler.
In 1920, Sam opened the Golden Pheasant tavern near Calvary Cemetery on Bluemound Road. And ten years later, he moved down the street to the Club Madrid in Brookfield, just across the county line from Milwaukee. The night club featured top entertainment, but was also a notorious gambling hangout.
Actress Hattie McDaniel worked as a waitress at the Club Madrid in 1929 and later performed there, before leaving for Hollywood in 1931 as the club took a beating in the depression.
Some people suspected Pick had connections to Capone, or some other Chicago gang figures, but nothing was ever proven. All anyone knew for sure was that a Chicago gangster identified as Thomas McGoorty fired on Pick in downtown Milwaukee on February 16, 1928, with Sam escaping death by hitting the floor. McGoorty ended up serving a life sentence in Illinois for shooting a deputy sheriff.
Bobby became a roulette wheel spinner in 1932, and was able to meet some of the club’s high class clientele, including actor Spencer Tracy. He left his father’s employ after a few years to sell football gambling cards — sometimes up to 30,000 a week — but lost money in this venture.
In March 1938, Sam and brother Joe were indicted for allowing gambling to be conducted in their club. Others rounded up were Garland “Gob” Buckeye, a former Milwaukee Brewer pitcher, and seventeen others, charged with either gambling or owning the slot machines that filled the establishment. Sam’s $2500 bond was paid for him by Steve Weber, a well-known Waukesha brewer. After a few months, the Picks pleaded guilty in June, and Sam and Joe were fined $1000 and $750, respectively.
Ironically, a year later, one of the grand jurors who indicted the Picks — Matthew J. Orth — teamed up with them to sponsor bingo games where 10% of the proceeds would go to the American Legion. He said despite being a gambler, Sam Pick was an honest man. Sheriff Alvin Redford saw it differently and pointed out that even bingo was considered illegal gambling under state law.
Bobby left Milwaukee during World War II to serve his country as a paratrooper. He was a true hero and distinguished himself by saving fifty men and single-handedly delievering ammunition to isolated troops in Carentan, Normandy. He was awarded a Purple Heart and was profiled in the Saturday Evening Post in September 1944.
When he got out of the service, Bobby worked on gambling boats off the coast of Florida. By the late 1940s, he was employed as a dealer in Las Vegas before the city had barely been built.
When he returned around 1950, he went back to work for his father, with the Club Madrid going strong through 1953, when the club burned to the ground. Joe died the same year. Sam decided to retire to Manitowish Waters (home of the notorious Little Bohemia Lodge), while Bobby remained in Milwaukee, living at 1917 North 34th Street. He also had a rented room at 1842 North 12th Street, where he set up Mafia associate Frank DeNicola with three telephones and various gambling paraphernalia. This would get both men evicted. (DeNicola was investigated in 1954 following the murder of mobster John DiTrapani.)
He opened a tavern on the corner of Reservoir Avenue and 12th Street. He played poker and had a horse book that he laid off with Frank Sansone. In the late 1950s, he took action from Sidney Brodson. In the early 1960s, Pick heard that gamblers in Milwaukee were being harassed by the Mafia.
One night at Gallagher’s, he was motioned into the bathroom by Steve DiSalvo. DiSalvo asked him if he had been pressured, and Pick said no and he would not pay if he was asked to. As Pick left the bathroom, a man with a pistol in his belt blocked the door, but DiSalvo waved him off.
Around this time, gamblers were having trouble paying Pick — one man who owed $6000 paid Pick instead with tropical fish. One of Pick’s bartenders was told by Vince and August Maniaci that Pick was to pay $100 a week, but Pick was never told to pay directly and never did. In the mid-1960s, Pick was sent to Sandstone Prison for gambling. He left his meager $5000 business with two men, and when he was out of prison six months later, they had lost it all. He started with a new partner, and within a few years, he lost $175,000 to the partner who embezzled it. Some of the money ended up with John Rizzo and a Racine attorney.
He moved to Marathon, Florida between 1968 and 1970, and began working for a sightseeing company as a boat captain. His Milwaukee ties stuck with him, though, when he was convicted of not paying taxes on $14,600 in gambling income for 1966. He was also charged with accepting bets from people over the phone in 1968. When the case came to trial in September 1972, defense attorney James Shellow convinced the jury that Pick was not guilty. He said gambler James Williamson was not a reliable witness when he said he placed bets with Pick, and the phone records did not prove Pick answered the phone. Housewife Grace Weber was arrested and charged with perjury after denying under oath she had placed bets with Pick: he went free while his clients took the fall.
Pick continued to provide the line to a friend in Milwaukee, who gave it to Halmo, who gave it to Brodson. Bobby claimed he only dealt with one bookmaker in Florida, a man in Islamorada.
Pick said he never regularly paid off the police, but on occasion he “threw them a bone”. He said Halmo once loaned a banker he met through Louis Fazio $50,000 but never got paid back; he did not know if Halmo was paying a share to the Mafia.
Super Bowl Sunday, January 13, 1974: Other raids were simultaneously made at the following residences: the home of Sidney Albert Brodson, 2420 East Stratford Court; Robert George Pick, 60, of Marathon, Florida; John Joseph Morn, 40, of Elm Grove; James G. Kops, 943 East Circle Drive; George Kermendy, 52, 3571 South 61st Street; Donald J. Danowski, 31, 1930 West Rogers Street; Richard I. Thoma, 36, 5419 North 83rd Street; and Russell J. Kent, 31, 614 South 63rd Street. No charges or arrests were made in these home raids, but information gathered was presented to a grand jury.
At Pick’s home in Marathon, Florida, the FBI (including Special Agent Sinecio Gutierrez) found eight sheets of paper in his guest bedroom tracking bets with names including “Bobby Pick” and “Halmo” written on them, 12 sheets of printed material in a living room desk drawer with football odds information from September through December, and eight more sheets of bets in the same desk. Taken were a telephone book and a “black telephone instrument”. Copies of Fans Weekly Sports Service and Weekly Sports Journal were found, as well as a couple of personal letters. Nothing was found on Pick’s person. During the search, two family friends (redacted) arrived at 3:25pm. A call came in at 3:35pm asking for “Bobby”. The caller would not identify himself or leave a message. The search ended at 5:15pm. (In my opinion, the evidence suggested that Pick was a much more minor player than Halmo, Brodson and Palmisano.) When told what the search was about, Pick said, “If that means telling (redacted) that Miami is 6 1/2 here, then I am guilty as hell.”
Bobby Pick voluntarily came in to the Milwaukee FBI office on January 24, 1974. He said he started gambling when he was 18 years old, working as a wheel roller for his father (Sam Pick) at the Club Madrid in Milwaukee on Bluemound Road, just over the county line. The Club Madrid had been a controversial gambling spot from the 1930s through the 1950s, and was a hangout for actor Spencer Tracy, but was not a Mafia-run business. Bobby Pick said he left his father’s employ but then went on to sell football gambling cards — sometimes up to 30,000 a week — but lost money in this venture. Pick then went into the Army, and when he got out worked on gambling boats off the coast of Florida.
On Wednesday, July 10, 1974, the Federal Grand Jury handed down gambling charges against 12 men: Steven John Halmo, 52, 716 South 7th Street; Robert George Pick, 60, of Marathon, Florida; Peter R. Marino, 42, 1924 West Clayton Crest; Sidney Albert Brodson, 65, 2420 East Stratford Court; August Palmisano, 45, 5358 North Kent Avenue; Eli Gukich, 48, of Waukesha; Raymond J. Dulski, 35, 4439 South 38th Street; Donald J. Danowski, 31, of Cudahy; Martin Azzolina, 32, 2419 North Cramer Street; Russell J. Kent, 31, 614 South 63rd Street; George F. Kermendy, 52, 3571 South 61st Street; and John J. Morn, 42, of Elm Grove. There were also 7 unindicted co-conspirators: James G. Kops, 39, 943 East Circle Drive; Richard I. Thoma, 39, 5419 North 83rd Street; Frank G. Spinella, 2832 North Summit Avenue; Michael R. Tullis of Las Vegas; James Spalding of Madison; Susan M. Werwinski of Las Vegas; and Theodore Cosmides of Madison. Brodson, Halmo, Azolina and Morn appeared in court and were released on $5000 signature bond. The others were given 24 hours to appear voluntarily in court before a warrant was issued for their arrest. Everyone turned themselves in on time.
Robert Pick appeared before Magistrate Peter Palermo in Miami on July 12, 1974 and was released on $5,000 personal recognizance bond.
On August 26, 1974, the FBI interviewed Edward J. Winslow in Hollywood, Florida concerning his knowledge of Milwaukee gambling. Winslow said he had previously lived in Milwaukee, but came to Florida almost twenty years ago and was employed in the security department of the Diplomat Hotel. He acknowledged knowing Steve Halmo and Sidney Brodson from the days when he owned a tavern in Milwaukee. He further said he knew Bobby Pick, and had been friends with him since childhood. Winslow said he occasionally talks to Halmo on the phone, and talks with Pick both on the phone and in person. He said Halmo and Brodson had notorious reputations as gamblers, though he had not heard that about Bobby Pick. Regardless, Winslow said he was in no way involved in any gambling activities.
Bobby Pick pleaded guilty to gambling charges (interstate transmission of wagering information) on November 26, 1974 under Rule 20. Judge Charles Fulton sentenced Pick to thirty days in jail and three years probation. He was expressly told to avoid gambling activities.
Steve Halmo made a voluntarily statement to the FBI on February 11, 1975. He said he was 53 years old, was born in Milwaukee, and knew Sidney Brodson as a professional gambler for the past ten years. They first met when Brodson wanted to bet with Halmo, but Halmo lost so much money in the first two weeks that he stopped letting Brodson bet. They soon teamed up together to bet with other bookies. About three years prior, Halmo learned that another gambler was getting his line through Bobby Pick in Florida, and Halmo and Brodson began making bets with Pick, too. Although Halmo makes Brodson’s bets for him (which allowed Halmo to keep part of the money), Brodson was aware that one line came from Bobby Pick and would ask about “Bobby’s line” or “the line from down south”.
Pick seems to have faded out of the law’s spotlight after the 1970s. He passed away in Monroe County, Florida on January 14, 1991.