A member of the Republican Party, Dwyer is known for his conservative positions on certain issues, including outspoken opposition to same-sex marriage in Maryland.

[8] On August 22, 2012, Dwyer was operating a motorboat on the Magothy River when he collided with another vessel, seriously injuring himself, John Moran IV, his companion and former police officer,[8] and five others.

[11] While he was appealing, early on the morning of August 20, 2013, Dwyer was pulled over by an Anne Arundel County sheriff's deputy in his 2001 Cadillac DeVille for suspected intoxication.

After showing signs of alcohol intoxication, failing field sobriety tests, and refusing a to submit to a breathalyzer examination, he was arrested and transported to the Eastern District for booking.

[13] Dwyer claimed his drinking that led to the boat accident was a result of marital problems and feeling betrayed by fellow lawmakers who supported legislation in favor of same-sex marriage in Maryland.