Dean was born in Memphis, Tennessee. His family attended a small Methodist Church, where he served as the assistant organist. He graduated from Princeton and attended law school and graduate school at Yale. He also spent a year at Cambridge. In the Yale library, he met Elizabeth Dante Cohen of New Haven, whom he married in 1971. They moved to Richmond when he joined Hunton & Williams, practicing public finance law. He was received into the Episcopal Church by Fletcher Lowe at the Church of the Holy Comforter. When the Popes moved to the far West End, Dean joined St. Mary’s, attracted by its services and sermons. He delivered the 2009 Lenten Lectures on the origins of the Anglican Church and has served on the Legacy Committee. Elizabeth passed away in 2021 after 50 years of marriage. Dean spends lots of time in Farmville with his son, Justin, Chief of Staff at Longwood University, daughter-in-law Maria Almond, psychiatrist and public health official, and granddaughters Aliza and Emilia, who serve as acolytes at Johns Memorial Episcopal Church.