He had the last laugh. He would ride to the top of the gambling racket by taking advantage of the very reforms passed to crack down on guys like him.

IN BOSTON, as in other cities, large-scale bookmaking started as a sideline for bootleggers who trafficked in illegal liquor during Prohibition. After 1930, when the Depression had set in, it got much, much bigger. By the 1950s, a state crime commission found that Boston was among the five top “layoff” destinations in the country, meaning bookies nationwide would lay off wagers with gambling outfits here to spread their risk. The commission estimated that, in 1954, total gross sales from illegal gambling in Massachusetts came to $2 billion. That was more than people in the state spent on food.

Essential to the business in an era when communication was interminably slow were wire services that distributed and handicapped the game and race results. Bookmakers needed up-to-the-minute information, partly to encourage lots of betting, but also to prevent past-posting — betting on races whose outcome they didn’t know but bettors did. The need for fast-paced wire services was a vulnerability on which authorities capitalized when they imposed a federal wagering tax in 1951. Gamblers would have to buy a $50 federal tax stamp and be liable for an excise tax on winnings. Hardly anyone was expected to pay it, but when bettors didn’t, they could be charged with tax evasion.

The law put the national wire services out of business. But when it became obvious that the Internal Revenue Service had nowhere near enough manpower to enforce it, local entrepreneurs popped up to fill the profitable void.

The first was a man named Harry Maltzman, who rented offices at 260 Tremont Street in 1952 and installed a bank of 17 phones, a radio receiver, a telegraph set, and a ticker tape machine that coughed up the results of races all over the country to be sold to bookies.

The second? Uncle Arthur.

ON MARCH 9, 1953, around the start of the New England racing season, Uncle Arthur opened a purported cleaning supplies company in Quincy as a front for his new wire service operation. He had seven phones installed and went into business providing race and game results for $20 a week apiece to what the FBI would later report were 100 bookmakers and drops: shoeshine parlors, barbershops, and other places bets were taken.

Just under 6 feet tall and 145 pounds, Uncle Arthur cut a dapper figure. In the mornings, he would make the rounds to settle up with customers. Then he’d schmooze with the fraternity of fellow bookies who hung out at Gordon’s Deli before the races got underway at noon. He always picked up the check. Neighbors questioned by the FBI called him an “extremely gentle and kind man,” but he was careful. He paid $1,000 a month to New England crime boss Raymond Patriarca for protection, signed office leases under the aliases “Arthur Gordon” and “Arthur Ronson,” and kept track of clients in a notebook not by their names, but by the cities where they lived: Chelsea, Everett, Revere. Bookies who called in identified themselves only by number.

Uncle Arthur hid in plain sight. In 1955, he applied for the installation of 12 more phone lines in an office on Harvard Street in Brookline, which he acknowledged would be used to furnish sports results to gamblers. After the police objected and the telephone company refused, the state Department of Public Utilities rejected Uncle Arthur’s audacious appeal — even though a legislator was his lawyer and another testified on his behalf.

Because the pay phones inside the tracks were locked up when racing was underway, Uncle Arthur and the other line men hired peeks to plant themselves outside the tracks and watch the tote boards through binoculars. On foggy days, they’d use runners. The schemes were eventually uncovered and resulted in a bill proposed by the Massachusetts Racing Commission to prohibit anyone from transmitting the results within a mile of a track until 30 minutes after any race. It didn’t pass.