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That year, aged 42, he was commissioned a first lieutenant in the Army's motor transport and went abroad to serve nearly a year in France. In 1920 he returned to politics, beat out Abraham Kaplan for Tammany leadership of his district. The next year he braved Boss Murphy's wrath to run against the organization's candidate for Borough President. He lost narrowly but thereafter was a power to be reckoned with.
Soon Hines became known as a big spender, a heavy bettor at racetracks. His family lived in style. Yet his reported income was modest, its sources vague. He filed no tax returns for the period 1929-35 until the Government cracked down. Then the following items were revealed: $3,300 a year for "services" to the Sun & Surf Club at Atlantic Beach, L. I.; $2,400 to $6,550 a year for "services" to the New Hampshire Breeders (Rockingham Park racetrack company); $4,000 to $5,000 a year from Kenway Construction Co. for "services."
In 1925-29, Mrs. Jimmy Hines had a sizable brokerage account. In 1929 a bank lent her $88,487.70 to pay off the brokers, took over her securities. Between 1929 and 1937, her bankers received $62,000 from unidentified sources for Mrs. Hines. Only once did Jimmy Hines have a brokerage account in his own name. Then he gambled in $38,000 worth of Johns-Manville stock, lost $5,458 in twelve days, settled with the brokers for $4,000. He and some friends borrowed $132,559.59 from Lawyer Max Steuer to buy 850 shares of stock in the New York Giants (baseball), on a tip that it would pay $25 a share.
Steuer got back some of his money, but lent Mrs. Hines some more and is now owed $52,000.
Where did the money come from? Mrs. Hines paid Jimmy's gambling losses with her checks, but he collected and kept his winnings in cash. The Hines family formed two office equipment and furniture companies to sell goods to the city for new buildings in 1935-37. One made $69,000 for the family, the other about $42,000. The District Attorney said that in 1928 Hines got $7,500 from a man & woman sentenced to prison in a "numbers" racket case. Their sentences were reduced. He acted as intermediary with the Tenement House Commission for several Bronx property owners. They gave him $4,000.
The Commissioner of Markets said that racketeering in the poultry market was reputedly "protected" by Hines, but this could not be proved. Neither could the District Attorney prove that Hines got $500 a month for permitting professional gambling in his Monongahela Club (political headquarters) in Harlem, or that Charles ("Lucky") Luciano, head of the prostitute trust (since jailed), was more than a social acquaintance of Jimmy Hines. He did stay at the same hotel and play golf with Luciano on a junket to Hot Springs, Ark. Another Hot Springs habitue was 'Legger Owney Madden (beer).