An era in Boston's history came to a close on Thursday as U.S. Federal Judge Denise Casper handed down a long-awaited sentence to James "Whitey" Bulger, the "Winter Hill Gang" boss who was convicted of 11 of 19 murders and 13 other crimes that included extortion,money-laundering, and weapons charges. He was sentenced to two life sentences plus five years and must pay restitution of $19,510,276.43. As an unnecessary addition, Bulger must undergo five years of supervised probation after his release.

During his long-delayed appointment with justice, Bulger was found guilty on a majority of the charges decades after the crimes were committed.

Before sentencing, Judge Casper spoke of the “unfathomable” crimes committed by the 84-year-old convicted Boston gangster as he stared emotionless and unresponding. Judge Casper started, “It is hard to know where to begin.” Then continued, “The scope, the callousness, the depravity of your crimes is almost unfathomable … it was all about money.”

Bulger began as an informant for the FBI in 1975 and the FBI turned a blind eye to Bulger’s ongoing criminal activities. Bulger would continue shaking down and killing his fellow criminals for almost two decades while he was under the FBI’s umbrella.

Bulger went on the lam for 16 years after being tipped off by his FBI handler, John Connolly, to the impending indictment under the RICO Act. It was in April of 1994 that unbeknownced to the FBI, a joint task force made up of the DEA, Massachusetts State Police and the Boston Police Department put together a probe of Bulger’s criminal activities. For 12 of those years, Bulger had a place on the FBI’s Most Wanted list.

Bulger disappeared with his long-time girlfriend Catherine Greig and there were many unconfirmed sightings of the famous fugitives throughout the years all around the globe. He had prepared well before-hand and had secreted money in numerous places and led a comfortable life on the run.

But, it all came to an end on June 22nd, 2011, when Bulger was apprehended by FBI agents and a Deputy U.S. Marshal in Santa Monica, California. The Task Force was tipped off by Anna Bjornsdottir, a former model and 1974 Miss Iceland living in that country. When apprehended, Bulger had over 30 firearms, as well as fake IDs and approximately $800,000 in cash in his apartment.

Bulger was arraigned in Federal Court in July, 2011, he pleaded not guilty to all charges.

In March of 2012, his girlfriend, Greig, pleaded Guilty to conspiracy to harbor a fugitive, identity fraud and conspiracy to commit identity fraud and was sentenced to eight years in federal prison.

In mid June of this year, Bulger himself would have his time in court, and when his trial ended in August, he was found guilty on 31 counts, including 11 murders.

Although sentenced to two life sentences, this may not be the end of Bulger’s life in court. He still faces indictments in Florida and Oklahoma.

In Florida, Bulger faces murder charges for the murder of John Callahan, the 45-year-old president of the World of Jai Alai, who was found filled full of bullet holes, and stuffed in the trunk of his Cadillac at the Miami International Airport.

In Oklahoma, Bulger faces charges for the death of 55-year-old Roger Wheeler, the former owner of the World of Jai Alai, who was murdered in his car following his weekly game of golf at the Southern Hills Country Club in Tulsa, Oklahoma. Wheeler had uncovered the embezzling operation at the World of Jai Alai. Bulger and another FBI informant, Steve Flemmi were told of the opportunity to skim funds there by former FBI agent turned Jai Alai Security Head H. Paul Rico. The Winter Hill gang would skim approximately $10,000 a week from the organization.

Wheeler’s investigation into the skimming operation would result in a half-dozen murders by the Winter Hill gang to cover up the scheme, and ultimately to Wheeler’s own death.

Bulger, Flemmi, and Johnny Martorano and two others would be indicted for Wheeler’s murder in 2001.

Two of the indicted died before being brought to justice, while Martorano would make a deal and confess to his part in Wheeler’s murder as well as to 20 other killings. He was sentenced to 15 years and served 6.

Flemmi is serving life in prison for his part in the murder.

Rico died of natural causes before he could be brought to trial.

Bulger may face the death penalty in those state cases.