Derek Gifford ’99 works the midnight shift

As a teenager, Derek Gifford ’99 developed two distinct interests: law enforcement and hip-hop music. Twenty years later, he has made his mark in both industries.

Derek Gifford ’99 works the midnight shift

Former Border Patrol agent Derek Gifford is now owner of the Chicago hip-hop night club D'Vine.

Derek Gifford ’99 works the midnight shift

As a teenager, Derek Gifford ’99 developed two distinct interests: law enforcement and hip-hop music. Twenty years later, he has made his mark in both industries.

When there is a disturbance at a nightclub, most owners keep their distance while the bouncers handle the matter. On the rare occasion when there is a problem at D’Vine, a hip-hop nightclub in Chicago, owner Derek Gifford admits his first instinct is to step in and restore order himself. It should come as no surprise. Most hip-hop nightclub owners don’t have ‘Border Patrol Agent’ on their resume.

Gifford’s unique career path started after he graduated college. With a degree in criminal justice and psychology in hand, he signed up with the United States Border Patrol.

“It seemed like a great way to pursue my interest in law enforcement and make a difference in a part of the country that I loved,” he says.

Before he could join the Border Patrol, Gifford completed a rigorous months-long training academy which covered topics like immigration law, Spanish, ethics and anti-terrorism techniques. He was then assigned to a station in Southern California.

Once on the front lines, Gifford — who had held no previous positions in law enforcement or the military — discovered the hard work was only beginning. The Border Patrol is responsible for monitoring thousands of miles of international land borders and coastal waters.

“The areas I was sent to patrol could change on a daily basis — rivers, the desert, the downtown area, you name it. I had to be ready for anything,” he says.

Despite the ever-changing assignments, one thing remained constant — the risk.

“I don’t think I am able to discuss the details, but I can say there were some interesting situations — usually involving car chases,” he says.

Life as a Border Patrol Agent also involved some long days and nights.

“We worked 40 hours a week, but we really had no control if certain situations happened that extended our day — like a standoff or a case pending in court,” he says.

Some incidents impacted the agents’ jobs more than others, but none more than the tragedies of September 11, 2001. The attacks on American soil led to a shift in the Border Patrol’s priorities — with an increased emphasis on the detection, apprehension and/or deterrence of terrorists and terrorist weapons.

The attacks impacted agents on a personal level, too.

“On the one hand, 9-11 reinforced the importance of what we were doing — protecting our country,” he says. “On the other hand, it got me thinking about spending more time with the people I love.”

After four years with the Border Patrol, Gifford moved back home to be closer to his family in Chicago’s northwest suburbs. When he arrived, some people assumed he would continue to pursue his career in law. Gifford had a slightly different idea.

“After giving it some thought, I decided I wanted to open my own hip-hop nightclub,” he says. “I have loved the music since I was little, listening to the likes of Doug E. Fresh and West Coast Rap.”

Of course, it is one thing to appreciate hip-hop music. It is quite another to own and operate a nightclub.

Gifford admits he did not have any idea what he would be getting into. “I just knew it was something I really wanted to do — so I went for it.”

In 2005, he bought a 1,700-square-foot club in the heart of Chicago called D’Vine. Not surprisingly, the first few months were a little overwhelming.

“Everything from the liquor license to staffing was all new to me,” he says. “There was a real learning curve.”

Without the benefit of any training to guide him, Gifford drew on his experience with the Border Patrol.

“I know it seems like two totally different worlds, but there were definitely things I learned while working for the Border Patrol that I put to good use when I started running D’Vine –— like how to stay cool under pressure,” he says. His late-night schedule as a Border Patrol Agent helped smooth the transition, too.

“The ‘midnight shift’ can wear on people who own nightclubs,” he says. “But I spent my last three years with the Border Patrol working from 10 p.m. to 6 a.m. five days a week, so I was already used to that kind of routine.”

As much as Gifford appreciated the unexpected ways his past pursuit helped prepare him for his current one, he has also reveled in their differences.

“When I was part of the Border Patrol, we didn’t have bouncers around, so we had to handle things ourselves,” he says. “I’ve learned that letting them handle the occasional problem that pops up here at the club makes my life a lot less stressful.”

He also discovered his new line of work offered him a level of autonomy he had never previously experienced.

“As long as the bank loan is continually paid off, I have total free rein at D’Vine,” he says. “The need for regiment and structure within the Border Patrol is understandable. But once I got a taste of that independence at D’Vine, I loved it. And I was determined to work as hard as I had to, to ensure I did not lose it.”

More than three years later, Gifford has continued to do just that — and he has shattered more than a few stereotypes along the way.

“I think the fact D’Vine remains open has probably defied conventional wisdom in an industry where clubs can go out of business quickly,” he says.

Gifford also breaks some common stereotypes about age, race and background. A hip-hop club may not seem to be the most typical spot for a self-described thirty-something white guy who grew up in the suburbs, but Gifford insists that is not a concern of his — or his clientele.

“At D’Vine, there is no real focus on race here — especially since the people who come here regularly know hip-hop music really is a lifelong love for me,” he says. “So more than anything, our guests care about things like Is the music good? Not the color of the skin of the guy who runs the place.”

Gifford does not fit the ‘hard-partying’ stereotypes frequently attached to the nightlife industry, either. Married earlier this year, he met his wife Ariele through church. Her father was his pastor for 20 years. He is also not a drinker, saying he has never tasted alcohol in his life.

“I did not get in the club business because I personally live a ‘fast’ life,” he says. “It was just a chance to work in an environment I have loved since I was little.”

It does not appear Gifford is in a rush to leave that environment any time soon. Still, given the man’s unlikely journey — from college student in Texas to Border Patrol Agent in California to hip-hop club owner in Chicago — and his penchant for taking his career in new and unexpected directions, one cannot help wondering what his next stop might be.

“Right now, I am happy where I am, running D’Vine,” he says. “In a few years, though, who knows? I have always had an interest in politics. I don’t have any actual experience running for office, but it is not like that kind of thing has stopped me before.”

Contact Gifford at