Whitey Bulger — sixteen years gone, undone by a daytime ad

In a rent-controlled apartment three blocks from the beach in Santa Monica, California, the FBI in June 2011 arrested James Joseph “Whitey” Bulger, the South Boston gang boss who had eluded a federal manhunt for sixteen years. He was eighty-one. His longtime companion, Catherine Greig, was taken with him. Inside the unit agents recovered more than thirty firearms, many hidden in holes cut into the walls, and roughly 822,000 dollars in cash. For more than a decade Bulger had lived under the name Charles “Charlie” Gasko, an unremarkable retiree among unremarkable retirees, while his face circulated on the FBI Ten Most Wanted list and a two-million-dollar reward stood unclaimed.

Bulger ran the Winter Hill Gang, the dominant Irish-American criminal organization in Boston, and for much of that reign he was also a paid FBI informant. The relationship was the engine of both his power and his escape. His handler, Special Agent John Connolly, fed him intelligence that helped him eliminate rivals and avoid prosecution, and in December 1994 Connolly tipped him that a sealed racketeering indictment was coming. Bulger left town before the arrests and did not surface again for sixteen years.

The trail did not break through brilliant detective work. It broke through advertising. In 2011, having concluded that the aging, disciplined Bulger was nearly invisible but his companion was not, the FBI ran a publicity campaign built around Greig — her manicures, her plastic surgery, her habits — and aimed it at the daytime television audience most likely to recognize her. A former neighbor in Santa Monica, a one-time Miss Iceland who had bonded with Greig over a stray cat, saw the coverage and called. Agents lured Bulger to the building’s garage and arrested him without a shot.

A federal jury convicted him in August 2013 on thirty-one of thirty-two counts, finding him responsible for eleven of the nineteen murders charged. He was sentenced to two consecutive life terms plus five years. On October 30, 2018, hours after being transferred to USP Hazelton in West Virginia, Bulger was beaten to death by other inmates. He was eighty-nine.