Growing up, DeKay enjoyed athletics, having played both varsity basketball and baseball, the latter of which is a generational tradition in his family.

DeKay attended Le Moyne College to study business and philosophy, where he also played baseball, eventually deciding to pursue a career in theater.

DeKay has guest-starred on several other TV series, including Friends, CSI, My Name Is Earl, NCIS, Scrubs, and Chuck.

[4] In June 2024, during Variety's TV Fest, DeKay confirmed his return as FBI Special Agent Peter Burke in the upcoming revival, "White Collar Renaissance".

DeKay also emphasized that the revival pays tribute to the late Willie Garson, who portrayed Mozzie in the original series.

[5] In May 2010, he returned to Le Moyne College as the commencement speaker and was awarded the degree of Doctor of Humane Letters honoris causa.