The native of Johnstown, Pa., knew little about the CFL in 1999 when he joined the Winnipeg Blue Bombers as a rookie free agent. Fourteen years later, Simon is close to leaving his mark as the most prolific receiver in league history.
Simon, 38, already the CFL's all-time receiving yards later, needs just six catches to eclipse Ben Cahoon's career mark of 1,017. And the Saskatchewan Roughriders veteran slotback can break the record Sunday night against his former team, the B.C. Lions.
"I didn't know much about the CFL when I came up here, I had bounced around the NFL and felt like I wasn't getting a fair shot," Simon said Wednesday during a conference call. "I just wanted to go somewhere where I was going to have an opportunity to play and I know if I got a true opportunity that I would do well.
"Obviously I didn't think I'd be No. 1 in the history of a league that's over 100 years old . . . when I first got here and looked at the record book and saw Allen Pitts (at 14,891 career yards) I just hoped to have just one 1000-yard season. I just wanted to play football no matter if it was north or south of the border, I just wanted a true opportunity to be a professional and show I can do it and at a high level."
The six-foot-two, 198-pound Simon is just one of three players in league history to accumulate over 1,000 career catches — Cahoon and Terry Vaughn are the others — and has amassed 16,128 yards and 103 TDs over his illustrious 15-year CFL career.
"Ben and I have been friends for a long time," Simon said. "He was a great player in this league and I'm honoured to have an opportunity to break a record of such a legendary player."
And if Simon scores a touchdown against B.C., he'll strike his traditional Superman pose.
"Of course," he said. "I feel fans expect that and it's something I've done throughout my career.
"It won't change since I'm playing B.C."
Simon spent his first two CFL seasons with Winnipeg before signing with B.C. as a free agent following the 2000 campaign. Simon's career took off with the Lions with six league all-star nominations and two Grey Cup titles (2006, '11). Simon also captured the CFL's outstanding player honour in '06 after registering 105 catches for 1,856 yards and 15 TDs, all career highs.
Simon was a model of consistency with B.C., registering nine straight 1,000-yard seasons. But he missed five games with hamstring injuries last year and was limited to 54 catches for 700 yards and two TDs.
Once the 2012 campaign ended, Simon was open to restructuring his contract with B.C. but had said if the club didn't want him back he'd look at playing elsewhere. Lions GM Wally Buono gave Simon and his camp permission to gauge interest in a potential trade, and on Jan. 24 the veteran was dealt to Saskatchewan for receiver Justin Harper and a 2014 third-round draft pick.
An upper body injury forced Simon to miss Saskatchewan's first three regular-season games. But when he joined the starting lineup, Simon's role was to mentor and complement young guns Chris Getzlaf, Weston Dressler and Taj Smith while providing a veteran presence and leadership.
"I think I bring a presence in the locker-room and on the sideline," Simon said. "I think I have a voice a lot of people will listen to because of the success I've had in the past . . . a lot of younger players come to me for my leadership.
"I give my opinion when needed and I think it's been working out pretty well because I do it in subtle way at times that maybe people don't understand but the message gets through."
Simon has registered just one 100-yard game this season, recording five catches for 125 yards and a TD in a 32-20 road win over Hamilton on July 27. Three times Simon has finished with five receptions in a contest, but has had two or less in the other five.
On Saturday, Simon faces his former B.C. teammates for the first time since the trade. Simon, who turned 38 last week, had five catches for 69 yards in last weekend's 31-29 loss to Toronto and has 23 receptions for 341 yards and three TDs this season.
But Simon has nothing to prove against the Lions.
"I'm excited for the week, I get to see some guys I've not seen in a long time," he said. "As cliche as it sounds, I have to treat this as any other game once it gets going.
"I'll be excited and ready to go just because I'll be playing against guys I practised against the last 10-to-12 years and have the opportunity to play against and try to get a win."
There's certainly plenty on the line as Saskatchewan (8-3) and B.C. (7-4) chase front-running Calgary (9-2) in the West Division. It's also the first of three head-to-head meetings between the Riders — who've lost two straight — and Lions with that being the tie-breaker should they end the season tied in the standings.
"Any time you play a divisional opponent it's huge," Simon said. "I know B.C. gets stronger during the year and that's one thing we're trying to do.
"This is going to be a huge game and I'm really looking forward to it. It happens to be against my old team. I'm not worried about who the opponent is, I just want to go out and win."
Simon says he's enjoyed playing in Regina, a football-mad city with no shortage of diehard fans who are rabid in their support of the Riders.
"I wanted to play football in a place where football was king," he said. "At times you can't go anywhere and hide . . . but at the same time people give you your space here.
"This is one of the warmest places I've ever been with people willing to help and just doing things for you. It has been an amazing experience to this point."
And it seems Riders fans will see a lot more of Simon. He intends on playing through the 2014 season before sitting down and determining his football future.
"Coming into my professional career I was on a 10-year plan and would've been happy just to play 10 years," he said. "Once I got to 10, I felt I was just getting going and starting to hit that momentum.
"I think I've got a lot left in the tank and feel I still have a lot I can do in this league."