Having been born into a musical family of nine, he began trumpet studies at age eight with his brother, Steve. Later he attended the Settlement Music School in Philadelphia and studied with Donald McComas of the Philadelphia Orchestra. He subsequently received a full scholarship to continue studies at Temple University. Upon graduation, he was named principal trumpet of the Media Theatre Orchestra. Strawley continued his study at the Manhattan School of Music with Vincent Penzarella of the New York Philharmonic.
In 1997, he accepted a position as Solo Cornet with the Naval Academy Band. He also served as principal trumpet with the Bay Street Brass Works, which won the New York Brass Conference Quintet Competition in 2003. Strawley also performed with the Pennsylvania Ballet Orchestra, Maryland Symphony, Annapolis Symphony and Mid Atlantic Symphony as principal trumpet. In 2006, he was appointed second trumpet with the Richmond Symphony and a member of the Mir Brass Quintet. He has been an adjunct instructor of trumpet at VCU since 2007.