Jim Brennan was plucked from Bristol City in October 1999 in a startling piece of good business by David Platt. He went on to make 146 appearances and flourished under Paul Hart as his exciting young team charged towards the play-offs.
Born in Ontario, he also made 49 appearances for his country.
Despite a healthy amount of appearances, he scored only one goal but a belter it was too. On a rare foray forward, he exchanged passes with Marlon Harewood on the edge of the box and drove a low, precise shot into the bottom corner of the Trent End goal. This effort saw off a hapless Norwich City who were impressed enough to snap him up when his contract came to an end. Maybe they thought he was a free-scoring full back. He wasn't.
He was though a fine player in a position which the club have consistently struggled to fill over the years.
More recently, he was coaching at Toronto FC, no doubt passing on his wisdom to Robbie Findley.
Here he is bagging a beauty for Toronto. Look out for a fleeting appearance from Danny Dichio too: