Corrupt law enforcement enables organized crime, as Whitey Bulger knew so well

Corrupt law enforcement enables organized crime, as Whitey Bulger knew so well
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James “Whitey” Bulger, the notorious head of the Winter Hill Gang in Boston, was recently found murdered in a West Virginia prison cell. The vicious beating, allegedly at the hands of mobsters, left Whitey unrecognizable. It seems the same brutality he practiced in life ushered him unceremoniously into the afterlife.

His death represents closure for many and the peeling-back of old wounds for others. Eventually… hopefully… for those in Boston, and for those impacted personally by the ravages of Whitey, the memory of him will completely fade into the oblivion in which he now resides.

But for those in the FBI, for those in law enforcement across all local, state and federal agencies – for those charged with the awesome responsibility of enforcing the laws, protecting the innocent, and upholding the constitution – they must never forget the story of Whitey Bulger and the corrupt FBI Agent John Connolly.


In 2012, while serving as the Acting Chief of the FBI’s Public Corruption Unit at FBIHQ, I was preparing with friends to attend the funeral of the mother of a college friend in Boston. I was aware of the connection the family had – through marriage – to one of the FBI’s former top ten Most Wanted fugitives, Whitey Bulger, but didn’t learn until the day before we were scheduled to leave that we were staying with family of the deceased at the family home of Stephen “the Rifleman” Flemmi, Whitey’s number two. Whitey had been arrested only months earlier and corrupt FBI Agent John Connolly had cast a dark and devious shadow over the city.

Under those circumstances, I had to consider: How might it look if the head of the FBI’s Public Corruption Unit stayed at the Flemmi family home? Not good.

So I skipped the funeral.

Billy Bulger, former state politician and Whitey’s brother, attended the wake.

Since then, I’ve had the unique opportunity to travel the world training law enforcement from four continents on the fundamentals of corruption investigations and the need for law enforcement to maintain the highest ethical standards. As a student of corruption, I have learned far more from those whom I have instructed than they from me.

It didn’t matter what part of the world I was in, the takeaway was often the same: Effective enforcement of the law requires community support, and that support is rooted in trust. Law enforcement cannot be successful without people in our communities providing information about illegal activity, supporting investigations, and facilitating change by refusing to participate in illegal activity.

Law enforcement corruption eats at the rule of law by destroying that trust which so many have worked tirelessly to build.

When communities stop trusting their law enforcement, everyone suffers.

Organized crime also relies heavily on the support of the community in which it operates – and that includes law enforcement, as evidenced by the relationship between John Connolly and Whitey Bulger. Not only does corruption facilitate organized crime, obstinate corruption is precisely what allows organized crime to thrive.

In the words of former Afghani parliamentarian Hossein Balkhi, “Corruption is the tree. Terrorism, destabilization, smuggling and poppy are its branches. If you cut down corruption, the rest will die.”


Whether it’s taking bribes in exchange for not writing a traffic ticket, waving a load of human smugglers into the country uncontested at a point of entry, protecting the transportation of dope across town, turning a blind eye to felonious activity, or tipping off Boston’s most notorious gangster that he’s about to be arrested (leading to a 16-year manhunt and multiple deaths), corruption of any kind tarnishes the badge for all the great men and women in law enforcement who remain vigilant.

Whitey Bulger engaged in horrific exploits during his life as a gangster. And for some, no amount of time will ever fully heal the wounds he’s inflicted.

But it was the actions of a corrupt FBI Agent by the name of John Connolly that sent Whitey on a nearly two decades long hiatus that ruined the reputation of the FBI in Boston, prevented the victims from receiving any semblance of timely justice, and allowed a deviant from Southie to soak in the sun in Santa Monica.

The FBI has put in place a number of protections to minimize the risk of another John Connolly making it through the ranks of the agency. But, in the end, it’s on every individual in law enforcement to hold themselves and each other accountable for who they are, how they act, and whether or not that badge on their chest shines.

Jeff Cortese, a financial crimes manager in the private sector, is the former acting chief of the FBI’s Public Corruption Unit. Before his 11-year career with the bureau, he worked as a dignitary protection agent with the U.S. Capitol Police and served on the security detail for the Speaker of the House. Follow him on Twitter @jeffreycortese.