Among the highlights of his tenure with San Diego,
according to a Colts.com story, was his recommendation to bypass drafting Michael Vick with the first overall pick in the 2001 NFL draft and instead trade the pick. The Chargers ended up drafting Hall of Fame finalist LaDanian Tomlinson with the fifth overall pick and selecting, on Raye's recommendation, future Hall of Fame quarterback Drew Brees in the second round. Raye also is credited with leading the group that recommended the Chargers sign a basketball player named Antonio Gates.
In his time with the Colts, Raye became "the most trusted confidant" of Grigson
“I think anyone will tell you that Jimmy Raye is the furthest thing from a ‘Yes Man’ there is in this league, and that is critical for someone in my position,”
Grigson told Colts.com. “Quite frankly I don’t like to hear some of his opinions sometimes, because I may be leaning very hard in a certain way and express a passionate position in an animated way, but Jimmy is someone who can hit you right back between the eyes with a well thought-out alternative perspective in a very matter of fact way.
“After it all marinates, I forget that he initially ticked me off and I say to myself, ‘Dang, I’m glad I have him.’”
According to Colts.com, Raye counts undrafted free agents Zach Kerr and Jonotthan Harrison, as well as seventh-round pick Denzelle Good, among his proudest finds.