Simon, a Toronto native, became a prominent junior hockey player not far from Buffalo. He played two seasons with the Niagara Falls Thunder of the Ontario Hockey League. He put together back to back monstrous season.
In 1990-91, while often playing with future Buffalo Sabre Brad May, Simon put up 51 goals and 125 points. Then in 1991-92 he led all Canadian junior hockey players in scoring with 146 points thanks to 53 goals and an amazing 93 points. He then posted 17 goals and 41 points in 17 playoff games.
Despite his incredible offensive production, Simon attracted little interest from the NHL. A major reason for that was Simon didn't make the OHL until he was 19 and then starred as an overage junior. Most top NHL prospects make juniors by the age of 17 and then are drafted at 18, but Simon wasn't even drafted until he was 20. The Sabres used their 10th pick, 203rd overall, in the weak 1992 draft to select Simon, who was a tiny center not known for his defensive game. Simply put - the NHL didn't think his high powered offensive game could be implemented at the NHL level. But as we all know, diamonds in the rough are always uncovered late in NHL drafts - selected immediately after Todd was a goalie drafted by the Winnipeg Jets named Nikolai Khabibulin.
Todd immediately went about proving the NHL wrong. He had an incredible rookie season with the Sabres' farm team in Rochester in 1992-93. Todd set a Rochester record for assists by a rookie with 66, and added 27 goals for 93 points in 67 games.
Todd took his game to a higher level in 1993-94. He scored 33 times and assisted on 52 others for 85 points in 55 games before he got his shot at the NHL. The Sabres called him up in late January and despite not playing a lot he ended the season in Buffalo. In 15 regular season games he pick up only 1 assist (against Los Angeles in just his second NHL game). He also appeared in 5 playoff games for Buffalo that season, and notched his first and only NHL goal in game 1 of the opening round against New Jersey.
When reflecting back at his 20 game trial at the NHL, Todd is disappointed he wasn't given a real opportunity to prove he belonged.
"I don't think I got a fair shot in Buffalo...I was only up 15 games and I didn't get to play much...I need lots of ice time to show what I can do. When you play only a couple of shifts, it's hard."
The 1994-95 lock out shortened season was a telling season for Todd. He played the entire season in the AHL and was not effected by the work stoppage, but never got a shot to return to the NHL when the labor dispute was settled. The Sabres went with the experience of the veterans in the truncated 48 game season, and when injury problems presented themselves, higher rated prospects were brought into Buffalo rather than Todd. This despite another strong season with 90 points in 69 games. That brought his three year totals while with the Rochester Americans to 268 points in 192 games.
However Sabres boss John Muckler didn't take a liking to the diminutive center. Todd was released by the Sabres following that season, and he found no NHL offer to his liking. Instead he jumped to the International Hockey League - a minor league which featured mainly players who couldn't get a full time NHL contract. he signed on with the Las Vegas Thunder and had an incredible 74 points in 52 games but found himself playing out the year with the Detroit Vipers, where he added 19 goals and 35 points to finish the season. The following season he finished third in IHL scoring with 105 points in 81 games.
Todd joined the Cincinnati Cyclones organization in 1997, and played three years in the Ohio city. Even when he signed a free agent contract with the NHL's Carolina Hurricanes in the summer of 1999, he returned to Cincinnati to play the season once he was cut from the Hurricane's training camp. He was never given consideration as a call up for the 'Canes.
Up until that season Todd never gave up on his dream of playing in the National Hockey League. A big part of him had always hoped that he would get another shot, and even though he went literally years without NHL offers, his dream spurred him on to one of the finest minor league careers of players in the 1990s.
Following the 1999-2000 season Todd looked to extend his career. "Symes," as he was nicknamed, ventured to Europe where he continues his hockey career in Germany.