Boschert was appointed by Governor Parris Glendening in 2000 as Executive Director of the Annapolis Regional Transportation Management Association.
In 2003, Boschert began a run for Congress in Maryland's 3rd Congressional District, but later withdrew to avoid a challenge by Bob Duckworth, who went on to be the Republican nominee.
Boschert subsequently chose to retire from the state House of Delegates and run for the Republican nomination for County Executive in 2006 to replace Janet Owens, who was term limited.
Later in his life, Boschert taught political science classes part-time at Anne Arundel Community College, located in Arnold, Maryland.
Later, Boschert returned to the good graces of the Republican Party in part by voting for the former Governor's proposals, including supporting the effort to install slots at racetracks.
Throughout his career, Boschert cultivated a moderate image, though he co-sponsored a Maryland state Constitutional Amendment banning gay marriage.