He began his criminal justice career as a police officer in Milford, Connecticut. In 1982, he moved his family to Port St. Lucie in St. Lucie County, and joined the Port St. Lucie Police Department. He worked there in a variety of assignments and rose to the rank of Commander.

In 1996, the Palm Beach Post named him Law Enforcement Officer of the Year. That same year, he was named Port St. Lucie Citizen of the Year.

He holds a criminal justice degree from Indian River Community College. He is a 2002 graduate of the 27th Session of the Senior Management Institute for Police which is located in Boston, Massachusetts. He is a 2006 graduate of the 39th Class of the Florida Criminal Justice Executive Institute.

He is Past President of the Fraternal Order of Police Lodge 118, Past President of the Port St. Lucie Breakfast Rotary Club and Past Executive Director of the Port St. Lucie Police Athletic League.

Former Governor Lawton Chiles appointed Chief Deputy Wilson to the Children’s Services Council of St. Lucie County. In 2000 Governor Jeb Bush reappointed him to the Council for another four years, totaling eight years on the Children’s Services Council.

Currently, Chief Deputy Wilson serves as the secretary/treasurer for the Treasure Coast Chief’s of Police and Sheriff’s Association. He serves as member of the New Horizons of the Treasure Coast Inc., Board of Directors as well as a member of the Boys and Girls Club of St. Lucie County.

In November 2000, he retired after 18 years with the Port St. Lucie Police Department to serve as Chief Deputy in the administration of Sheriff Ken J. Mascara.