He won the CFL's Most Outstanding Player Award in 2006 while also winning three Grey Cup championships; with the BC Lions in 2006 and 2011 and with Saskatchewan in 2013.

[2] Following his playing career, Simon was an executive in the Canadian Football League and was the interim general manager of the Edmonton Elks in 2024.

Simon finished second on the University of Maryland's all-time charts for receptions (185) and receiving yards (2,059), and caught 10 career touchdown passes.

2001: Joined the BC Lions as a free agent and served as a backup at the slotback position, seeing time in 6 games.

He broke Darren Flutie's BC Lions team record for single season receiving with 1,750 yards.

Evidenced by his dominant play, Simon was named the CFL Offensive Player of the Month for both September and October.

However, it turned out that he had saved his best for last and caught 38 passes for 859 yards and six touchdowns in the final eight games, incidentally, all wins for the Lions.

He set a personal best 18.2-yard average per catch and claimed his second straight receiving title with a 211-yard performance in the final game of the season.

2012: On 29 June, while playing against the Winnipeg Blue Bombers and with the former record holder Milt Stegall in attendance, Simon became the all-time CFL career reception yards leader.

[11][12] Before ultimately choosing football as a career, Simon enjoyed great success as a basketball player at a young age.

Simon currently lives in Edmonton for the football season and spends the offseason in Arizona with his fianceé Taryn Dakha.

[15][16] After Simon ended his playing career in 2013, he remained with the Saskatchewan Roughriders in a front office role.

[19] On November 9, 2024, it was announced that Ed Hervey had been named general manager for the Elks and Simon was not retained.

[20] In 2012, in honour of the 100th Grey Cup, Canada Post used his image on a series of commemorative postage stamps.

The image was also used on presentation posters and other materials to promote the Grey Cup game and other celebrations associated with the centennial.