Caldwell was a 4-year starter at Defensive Back while with the Hawkeyes. He learned a lot from Bob Commings and became a graduate assistant in 1977 and that began his coaching career. He would then leave Iowa for Southern Illinois as their Wide Receiver Coach, a title he would hold for Colorado and Louisville. He also pit-stopped for a year at Northwestern as an Offensive Assistant and found his way to Penn State as a Wide Receiver Coach, only to take over the next year as Quarterbacks Coach under Joe Paterno. It was there that he coached Kerry Collins when he was named the best Quarterback in the country by winning the Davey O'Brien Award. He remained there for 7 years before being named the Head Coach of the Wake Forest Deamon Deacons. He remained there for 7 years as well, while giving the Deamon Deacons their first winning season in 6 seasons and being selected for a bowl game as well. Jim eventually made his way into the NFL in 2001 with the Tampa Bay Buccaneers as their Quarterbacks Coach, but followed Tony Dungy to Indianapolis in the same role. In 2005 he added the title of Assistant Head Coach and was a big part of the Colts winning the Super Bowl with his tutelage of Peyton Manning. In 2009 he took over as Head Coach for the Indianapolis Colts when Dungy retired after the season. He became the first ever rookie Head Coach to start a season 14-0 in 2009, before the Colts were beaten in Week 16 by the New York Jets. The game was considered controversial because Coach Caldwell decided to rest the majority of his starters to keep them healthy for the playoffs, thus not striving for the perfect season.
