For some people an ordinary and routine life just doesn't seem to have enough allure to have them settle down and grow roots. Notoriety is the order of the day for them. For various reasons be it financial, nationalistic, religious or simply thrill-seeking, certain individuals throw away the blanket of societal structure and embark upon a life of crime and being on the run. Not lucky enough to actually get away with it, these individuals resort to Plan B; get out of dodge as soon as possible and stay away as long as possible. Success in the fugitive lifestyle isn't gauged simply by how long a fugitive remains on the lam, there are other contributing factors that might bump up a fugitive's successful status; such as how openly he or she lives in their wanted status and the financial and material quality of the life they live.
5 James "Whitey" Bulger
James "Whitey" Bulger was the notorious leader of the South Boston based Winter Hill Gang. Born into a poor working class Irish Catholic family in the city of South Boston, Massachusetts, James Bulger did not take long to land himself in a life of crime. Some early juvenile criminal acts landed him in reform schools before being released again. After being discharged from the Air Force he started to move up in the criminal world, spending time behind bars in Atlanta Penitentiary and the infamous Alcatraz Prison. After his release and nine years in jail behind him, Bulger began his steady rise in his home town, setting up the Winter Hill Gang that saw its heyday in the 1980's with weekly shakedowns of local businesses, illegal gambling, loan sharking, drug and arms trafficking and various other racketeering activities. His profile was so elevated that his gang had even infiltrated the Police and the FBI. All this of course did not stop Bulger from becoming an FBI informant himself, virtually disowning the Omerta code of silence among criminals. Bulger's fortunes started to wane in the early 1990's, and in 1995 he was forced to go on the run when one of his FBI informants gave him a heads-up that a criminal task force was on its way to arrest him. For the next sixteen years, James "Whitey" Bulger went from safe location to safe location, even making it to number two on the FBI's most wanted list. Despite some confirmed and unconfirmed sightings in London, Italy, Uruguay and France he was finally apprehended in Santa Monica, USA of all places in 2011.
4 Ratko Mladic
The next individual on the list is Serbian Colonel General Ratko Mladic. Mladic was born in 1942 during the height of WWII in Yugoslavia. His father was killed in action fighting against the occupying Nazi forces and his mother was forced to raise three children on her own. After finishing high school Mladic enrolled into the Military Academy, and then went on to the Officers Academy. Over the years and decades he steadily rose through the ranks via his studious ways and good leadership skills. By the time the Former Yugoslavia started disintegrating in 1991, Mladic was a Lt. Colonel General. The conflict in the Former Yugoslavia took a very sectarian and ethnic turn right from the beginning, pitting Serbs against Croats and Bosniak Muslims. The worst of the fighting took place in the Republic of Bosnia, the most ethnically and religiously diverse of all the former Republics. Here Mladic's military tactics came to the forefront. He laid siege to the city of Sarajevo for four years, the longest siege in modern military history, cutting off supplies and reducing it to rubble via artillery strikes. The citizens and trapped soldiers of Sarajevo also had to contend with another harrowing tactic of Mladic. Near continuous sniping by Serb soldiers entrenched in the hills overlooking the city, paralyzing the people in fear of movement. Mladic's notoriety though is largely know for his orchestrated Srebenica massacre in 1995, where his troops executed 8,000 Bosniak Muslim men and boys in one day. For this he was branded a war criminal by The International Criminal Tribunal for the former Yugoslavia(ICTY) and was forced to go in hiding after the war ended in defeat for Serb forces. What made Mladic a successful fugitive was that he was virtually unafraid to live out in the open, being provided political protection by various elements within the Serb government. Allowing him to go to trendy restaurants and even weddings. Eventually though this protection ran out as a new, younger leadership in Serbia took over and decided to hand Mladic in 2011 to the Hague Criminal Court to account for his crimes.
3 Osama Bin Laden
Osama Bin Laden is arguably the best known contemporary fugitive, even if he no longer is one. Best known though does not always equate to most successful. Osama Bin Laden was born into a wealthy Saudi-Yemeni family. His father owned the Bin Laden construction consortium and was worth several billions of dollars. Suffice to say Bin laden never wanted for anything, living a princely life with a silver spoon in his mouth. But like all spoiled and pampered children he took the road of rebellion. Giving up on his life of riches he embarked on a journey to Afghanistan and wage Jihad or holy war against the Soviet Union that had invaded the nation in 1979. Though not one to do the dirty work himself, Bin Laden used daddy's money to finance the operations of the Mujahideen or holy warriors. After the Soviet's withdrew in defeat ten years later in 1989 Afghanistan's warlords turned on one another and Bin Laden was welcomed back as a hero in his native country. This honeymoon wouldn't last long as in 1991 Bin Laden was angered by the Saudi Monarchy's decision to station American troops during the Gulf War. He was eventually kicked out of Saudi Arabia, moving on to Sudan and then eventually back to Afghanistan. All the while planning and carrying out terrorist attacks against U.S. targets in 1996, 1998 and 2000. These attacks culminated with the 9/11 attacks in 2001 on American soil. This prompted the U.S. to launch an invasion of Afghanistan, overthrow the Taliban regime harboring Bin Laden and capturing the mastermind. Bin laden evaded capture when it seemed imminent and found refuge in Pakistan. It wouldn't be until 2011 almost a decade after 9/11 that he would be hunted down and killed in a covert raid by U.S. Navy SEALs in the affluent Pakistani city of Abbottabad.
2 Mullah Mohammed Omar
The next person on the list is the wily and obscure Mullah Mohammed Omar; the spiritual founder of the Taliban movement. A Pashtun dominated Islamic fundamentalist terror group. Very little is known about Mullah's Omar's background as he is known to be extremely secretive and paranoid. So secretive that there is only one short video recording of him from afar that has been considered an authentic image of him. Mullah Omar got his start in the Islamic extremist circles much like his ally Osama Bin Laden, mentioned above. After waging war against the Soviets for nearly a decade and losing an eye in the process, Mullah Omar turned to the daily problems of Afghanistan; warlords vying for power. Fed up with all the squabbling and infighting Mullah Omar created his own militia called Taliban, or students. In a relatively quick amount of time Omar's students had overrun the entire country and established de-facto control. They then set out to transform Afghanistan into one of the most puritanically religious nations on earth, banning a host of normal activities, like watching TV, listening to music and even flying kites. After 9/11 and the toppling of his regime, Omar fled like many of his peers to Pakistan, where he is reputed to stay in hiding to this day, possibly under the protection of the ISI, Pakistani intelligence services under a loose form of house arrest.
1 Semyon Mogilevich
And the winner of this contest is....Semyon Mogilevich. The reputed head of the Ukrainian Mafia. If its big, this guy has a share in it. If its illegal, he owns it. Semyon Mogilevich like all criminals started out small, but like his girth suggests success was not that far behind. He eventually climbed to the top position of head boss of several Eastern European crime syndicates and set about enriching himself via some of the most sophisticated schemes known to man. From wire fraud and money laundering to owning entire armaments factories to sell illegal weapons all over the world, Mogilevich has his fingers in all the pies. Despite the best efforts of the FBI and other law enforcement agencies to apprehend and bring him to justice, Mogilevich has simply insulated himself far too well with the protection of various governments, particularly Russia, from being captured and prosecuted. He lives openly and freely in Moscow, attending cultural and sporting events without fear and dining in some of the most posh restaurants of the city. Thus making him the most successful fugitive alive for having accomplished all the goals; evading the law, living in the open and free from apprehension and in the process, being filthy rich.