Derek started out competing in Powerlifting and progressed to become the Connecticut State Champion. He started competing in Strongman after finding an advertisement for a contest on the back of a Powerlifting flyer. After earning his Professional Strongman card from the ASC (American Strongman Corporation), Derek took two years off competing to enter the Police Academy and become a Police Officer. He returned to competing in Strongman, and placed 5th in the 2006 St. Patrick's Strongman National Qualifier.
Derek then went on to place 2nd to the current IFSA World Champion Zydrunas Savickas in the 2006 World Strongman Challenge contest in Tulsa, Oklahoma.
Next up, Derek placed 5th in the 2006 America's Strongest Man USA National Championship. This earned him an invite to the 2006 IFSA (International Federation of Strength Athletes) World Championship.
On October 26, 2006, two weeks before the World Championships, Derek severely injured his lumbar spine during training while attempting a maximum effort deadlift of 366 kg (805 lb). Derek had a lumbar disc herniation (L4/5) and a massive spinal cord hemorrhage. Doctors told him that he would never lift again due to the severity of the injury.