On June 22, 2011, after 16 years on the run from law enforcement, James “Whitey” Bulger, a violent Boston mob boss wanted for 19 murders, is arrested in Santa Monica, California. The 81-year-old Bulger, one of the FBI’s “10 Most Wanted” fugitives, was arrested with his longtime companion, 60-year-old Catherine Greig, who fled Massachusetts with the gangster in late 1994, shortly before he was to be indicted on federal criminal charges. At the time of his 2011 arrest, there was a $2 million reward for information leading to Bulger’s capture, the largest amount ever offered by the agency for a domestic fugitive.

Born in Massachusetts in 1929 and raised in a South Boston housing project, Bulger, who earned his nickname as a child for his light blond hair, served time in federal prison in the 1950s and early 1960s for bank robbery. Afterward, he returned to Boston, where he eventually built an organized-crime empire with partner Stephen Flemmi. At the time the two men were involved with drug trafficking, extortion, murder and other illegal activities, they were serving, since the mid-1970s, as FBI informants, providing information about rival mobsters in return from protection from prosecution.

After a rogue FBI agent tipped off Bulger that he would soon be arrested on racketeering charges, Bulger disappeared in December 1994. (John Connolly, the agent who tipped off Bulger, was later convicted on charges of racketeering, obstruction of justice and second-degree murder.) Despite an international manhunt, Bulger eluded authorities for over a decade and a half. Then, on June 20, 2011, the FBI employed a new tactic by airing a public service announcement focused on Greig, Bulger’s companion. The ad, which aired in cities across the U.S. where the mobster was thought to have once lived or have contacts, was aimed at female viewers who might have seen Greig, who underwent a variety of cosmetic surgeries, at a beauty parlor or doctor’s office. Based on one of the tips they received, FBI agents staked out Bulger and Greig, then going by the names Charles and Carol Gasko, and arrested them without incident at the modest, two-bedroom Southern California apartment building they had long called home.

Law enforcement officials found weapons, fake identification and more than $800,000 stashed in Bulger’s apartment. He later revealed to them that during his years on the lam he had traveled frequently to such places as Boston, Mexico and Las Vegas, armed and sometimes in disguise.

After their arrest, Bulger and Greig were returned to Boston. In June 2012, as part of a plea agreement, Greig was sentenced to eight years in prison for helping Bulger remain in hiding. The following summer, Bulger went on trial, and on August 12, 2013, he was convicted in a federal court in Boston of 31 of the 32 counts against him, including participating in 11 murders and other criminal acts.

On November 14, 2013, a federal judge sentenced Bulger to two life terms in prison plus five years. He died while incarcerated on October 30, 2018.