Makowsky has played his entire CFL career with the Saskatchewan Roughriders. He was drafted in the second fround of the 1995 CFL college draft from the University of Saskatchewan. In 2008, Makowsky became the first person to win three Oustanding Offensive Lineman awards, having won it previously in 2004 and 2005. Makowski has won five West All-Stars (2004-2008) and four CFL All-Stars (2004, 2005, 2006 and 2008). Makowski has most often played tackle, but thad moved to guard and even center when needed. Makowsky was a member of the Roughrider team that won the Grey Cup in 2007, the third in franchise history.
Makowsky had one pass reception for -3 in yards in 1999.