Even back in the late 80s, Jack Riley knew his job was about more than just drug busts. But he also found that a good bust was a thing to relish. In 1987 Chicago, like other American cities, was awash in cocaine from Central and South America, and sales of it had moved into the open. Residents of the west-side Austin neighborhood were complaining to the police that dealers had set up shop in and around the Washington Pines, a seven-story apartment hotel where men were seen hanging out in the lobby all day and night. Business was so brisk that neighbors had taken to calling the area “Crack City.”
Top Cat was an old acquaintance of the manager of the hotel, who happened to be an infamous police officer named Nedrick Miller. “He was the Outfit’s muscle in the black community,” Maloney says. “A lot of police officers liked him because if you had an issue on the west side he could fix it. You’d mention Rick Miller’s name [to cops], and if they hated him, they were straight. If they said, ‘Hey, Rick’s a good guy,’ you knew.”
It turned out that the men were underlings of a top mobster named Anthony “the Hat” Zizzo. One member of the operation was a Chicago police officer who made trips to Florida to pick up cocaine from a Colombian source. Others were also trafficking in stolen goods and overseeing gambling operations. Area business owners were told their legs would be broken if they didn’t cooperate.
The city of Chicago has led the country in murders for the last two years, outpacing its larger rivals, New York and Los Angeles. The daily bloodshed is fueled at least in part by a drug trade that’s replaced the legal economy in many neighborhoods where disputes are settled with guns.
Heroin use and overdoses were soaring nationally by the time Richard Nixon created the DEA in 1972 with a vow to fight traffickers as well as street distributors. Two years later, the top DEA official in the midwest told the Tribune that Chicago’s role as a transportation center had turned it into the nation’s “hub” for trafficking heroin.
There were relatively few regulations in place for DEA agents, meaning even rookies were given the latitude to improvise along the way. “We just were running by the seat of our pants half the time—we didn’t have much supervision back then,” recalls Maloney, who was Riley’s first DEA partner.
