01/30/2014 01:25 pm ET Updated Apr 01, 2014

A Portrait of Two Pirates: Smuggler and Enforcer in the World of Drug Trafficking

Reading the New York Times last Sunday, I was mortified to discover the story of Ross Ulbricht, the alleged mastermind known as Dread Pirate Roberts who was behind the multimillion dollar online drug hub, Silk Road.

What's described as "an eBay for the illicit", Silk Road was an encrypted site that made drug deals through untraceable Bitcoins. By retaining between 8-15 percent of every transaction, the 29-year-old began profiting from the black market, with nary a footprint in the sand or blip on the map to reveal his identity, whereabouts, or methods to family, friends, and the Feds. As if this massive underground Internet trade was not enough, DPR also faces murder-for hire charges on five individuals who threatened to unveil Silk Road. While no incidents were reported, and one was in fact staged by federal officials, the alleged attempts were enough for Ulbricht to be denied bail.

What makes the story even more shocking is that this cyber drug lord is a former Eagle Scout who holds a master's degree in material sciences and engineering from Penn State. This handsome, all-American young man is the same person who ordered nine fake IDs which helped make him a "person of interest" for the FBI. While the details are not clear on how the FBI brought Ulbricht down, weeks after the ID package was found, the FBI located and copied the Silk Road's main servers. Along with Ulbricht's denial that he is the Dread Pirate Roberts, the methods in which the FBI used to acquire the servers will be at heart of his defense strategy. The contradictions in Ulbricht's story run deep. Beyond having an alleged double life, the New York Times columnist David Segal describes him as, "a humanitarian willing to kill, a criminal with a strict code of ethics."

Contrast this pirate with Jay Dobyns. Jay was an all-American boy with whom I went to high school and college. As quarterback of the football team, he played for the University of Arizona Wildcats. He was an upstanding and principled young man, someone who made our high school and our college proud. So imagine my complete surprise to see Jay at my ten-year high school reunion in 1990, sporting a skull cap and full-body tattoos like Ray Bradbury's Illustrated Man. Although Arizona is a landlocked state, I pictured Jay at the time as a pirate sailing around the open seas looking for, as in the song Born to be Wild, "adventure and whatever comes my way." In the sea of people that night, I didn't get to talk to Jay. I just marveled from afar that he looked most unlike the man I knew at graduation and least like the high school yearbook predictions of him.

Unbeknownst to me or anyone in 1991, Jay had created this persona as an agent for the Bureau of Alcohol, Tobacco, and Firearms (ATF) to infiltrate the hard-to-crack drug trafficking practices of the Hells Angels. In his 2009 memoir No Angel: My Harrowing Undercover Journey to the Inner Circle of the Hells Angels, Jay chronicles his escapades before and after his gun wound on the fourth day of his ATF job. Jay was shot in the back by a drug addict, the bullet entering Jay's lung and exiting his chest. Once an athlete with NFL dreams, Jay now lay bleeding to death. His life was saved by a skilled trauma surgeon and Jay decided to take the gun wound as a reason to deepen his resolve. "Being shot showed me that I wanted to be the guy that would stand up to the violence on behalf of my community," Jay shares.

Instead of the encrypted cyber-world where DPR sailed his ship, Jay rode a monkey bar Harley and wore a red bandana. Risking his own life and that of his family, Jay maintained an inner core of justice and integrity in the midst of unnerving, constant danger. Following his 17 years as an undercover agent, Jay needed to restore his faith in humanity. He traveled to and still works with an African-based non-profit that provides clean water systems and medical care to orphans in Ghana, West Africa.

While DPR's black market put billions of dollars of drugs in the hands of dealers and addicts, he was motivated by something much bigger; he wanted to change the world. With a political manifesto that demanded less government, he created a place where he could bring in millions that the government couldn't touch. Jay also demanded change. He set out on his bike to end drug trafficking and to protect his community. Though the operation was successful, his choice came at the high price of putting himself and his family in danger. Both of these men were faced with unconventional choices that came with no guarantees, no matter if the execution and intentions were for good.

It behooves students beginning college, or young adults with a hankering for the high life of danger and riches, to think about the risks and rewards inherent in the lives of these two metaphorical pirates -- one a drug lord of sorts and one a law enforcer. Whom would you most like to emulate? Whose courage will improve the world? What choices do you want to make?

You can read more about Jay and many other college and career role models in the KEYS TO SUCCESS 7th edition by Carol Carter and Sarah Kravits, published by Pearson Education. Watch for other role models for college and career success in the coming days.