From the new lad at Bristol City to the iron man at Toronto FC, Brennan makes a statement wherever he plays. Put him in the back line, and he's a rock defensively. Throw him up front, and he's a menace on the left flank. Play him in the midfield, and his pinpoint passing dictates the game. Follow Jimmy's career across two countries, six clubs and hundreds of matches.
Jimmy holds a few firsts in Toronto FC's record books. Not only was he the club's first player, but he was also named the side's first captain. And in 2007, Brennan became the first Canadian to score for the club with a stunning free kick against the Columbus Crew.
Toronto's captain proved his versatility in the club's inaugural season. Despite playing out of position in central defence, he proved to be the most reliable man in the squad - starting all 27 league matches and playing through injury. He personified what it is to lead from the back.
Toronto built a deeper squad in the following seasons, allowing Jimmy to play on his favoured left side. With the extra freedom, he wreaks havoc all along the left touchline, tackling hard at the back and bombing forward to attack.
2007 -
2007 -
Brennan was made a Saint in early 2006 when he signed with Southampton. After half a season at St. Mary's and 14 appearances for the club, Jimmy made a trip home to Toronto.
2006 - 07
2006 - 07
After four seasons with Forest, Jimmy made the move south to fellow First Division side Norwich City on a Bosman transfer. Brennan battled injuries for much of his time with the Canaries and made fewer appearances than he would've liked.
Still, he managed to bag a pair of goals in 9 appearances during the 2003-2004 season. Norwich won the First Division title that same year and earned promotion to the Premiership.
2003 - 06
2003 - 06
Forest holds a special place for Jimmy. He racked up well over 100 appearances for the First Division club and loved every minute on the pitch. He truly felt part of a proud history. Not only was he playing in a skilled side, but Jimmy represented a club with European Cup glory to its name. Seeing the legendary Forest greats around The City Ground was a source of inspiration for him.
While at Forest, Jimmy played under the brilliant Paul Hart, a manager known for innovative tactics. Hart's diamond formation proved instrumental in Forest's success, and the club reached the First Division playoff semifinal in 2003. During this period, Jimmy was lucky enough to play alongside defender Des Walker, who helped hone his tackling.
Along with Toronto FC, Forest is Brennan's team. He's a lifelong Red.
1999 - 03
1999 - 03
Bristol City was where it all began for a then 16-year-old Brennan. His rise to the first team is the stuff every kid dreams about. Starting in the youth team, Jimmy worked hard and made it into the reserves. From there, he impressed enough to earn a place in the senior squad and eventually the starting 11.
Jimmy learned his trade in Bristol, thanks to coaches like Joe Jordan and veteran players like Brian Tinnion. These two looked after Brennan and taught him the ins and outs of the game. His Bristol career developed the technical skills and physical strength that made a name for him throughout the division.
He also netted his first professional goal at Ashton Gate after a slick one-two with Tinnion, who had the best left foot Jimmy has ever played with. After slotting it into the bottom corner, Brennan ran to the stadium's Dolman Stand and pointed to his name on the back of his jersey. He took some stick from his teammates, but the City fans knew exactly which name to shout.
After four seasons at City, Jimmy made the move to the Midlands and signed with Nottingham Forest.
1996 - 99
1996 - 99