Dennis is the family lawyer of the Wagner family. He apparently had a close friendship with Maurice Wagner and appears to have known Holly since she was a child. Holly holds him great respect as a family member. Dennis didn’t appear to known about Dan Ferrell’s secret conspiracy with his Belgian friends to perform a gruesome ritual for Lady Luck. He met Holly’s new husband John Trick, however he was quick to show disdain for him. He considered John (Jack Horner) to be a golddigger and very untrustworthy. He then noted that this wasn’t the first time that Holly had gotten married, meaning he might have arranged it for her previous marriages to be annulled. However, despite how he distrusted Jack, the marriage seemed valid.
He would get a big shock when Holly and Maurice were killed in a horrible car bomb, made to look like an accident. He was distraught to know the people he loved as family were gone. Jack was the only survivor, trying to put things aside, given their loss, he told Jack that all of Maurice’s fortune went to him. Jack was obviously pleased. Its unknown why or when but Dennis was later getting tired of Jack having the fortune.
Most likely it was due to Jack’s actions after getting the inheritance such as spending it recklessly and also sleeping with other women, when he should have been grieving over Holly. Dennis did find a loophole in the will, Jack could lose his fortune if he did a horrible things, such as murder. Dennis framed Jack in the murder of Dan Ferrell, even though he did it. Possibly his own personal revenge. After Jack and Gary escaped the police, Dennis most likely got Maurice’s fortune.