[2] Caldwell was educated at Upper Canada College (UCC), a private high school, graduating in 1991.
[6] In 2002, Caldwell offered $150,000 in an unsuccessful bid to purchase Frank magazine hoping to change it into a "kinder and gentler" publication.
In August 2008, Theo Caldwell was recognized as the Canadian Institute for Jewish Research Golden Magen Davidhonoree for outstanding person of the year, for his support of Israel in the columns of Sun Media properties and in the National Post.
[18] Caldwell's short tenure at Sun received further notice in November 2011 when Sun News reprinted a group photo from its launch in which Caldwell's image was pasted over "with a discoloured, mildly out-of-proportion image of his replacement, Toronto radio host Michael Coren.
"[18] From 2014 until the fall of 2015, Caldwell hosted a weekly hourlong show, Saturday nights on CFRB radio, which was later cancelled.