As Simon sat in the Lions dressing room at the club's training facility Thursday, he was officially a member of the Saskatchewan Roughriders. Simon, the CFL's all-time receiving yards leader, was traded earlier in the day in exchange for receiver Justin Harper and a third-round pick in the 2014 Canadian college draft.
But as Simon said goodbye after 12 seasons in a Lions uniform, the longtime face of the franchise had trouble letting go.
"This has been the toughest decision I've ever had to make in my professional life," Simon said during a news conference. "This is a tough day. This is a very tough day. But in the end this is a decision we had to make."
Lions general manager Wally Buono said the decision to trade the popular slotback was mutually agreed upon by Simon and the club after the team indicated Simon's role with the team was likely going to change this upcoming season. Buono also wanted Simon to take a pay cut, the extent of which Simon was unwilling to accept.
In an unusual scene, Buono sat next to Simon after trading him. Noting the club did not give other former players such treatment, Buono said he had to separate his emotions from his personal feelings, but the trade was difficult for him.
"When I woke up this morning, I felt like I was going to a funeral," said Buono.
Buono said he sat down with Simon to discuss "the next step" for the receiver's role with the franchise, and the two sides agreed that a trade would be the best option.
"He has to fit in and he has to want to fit in," Buono said when asked of the decision to trade Simon.
"For us to part ways is not something we enjoy," Buono added. "But it's a part of the sport that you have to deal with."
A two-time Grey Cup champ and six-time CFL all-star, Simon has recorded 15,787 yards over his 14-year career.
Hamstring problems forced him to miss five games last year, limiting him to 54 catches for 700 yards and two touchdowns. It marked the first time in 10 seasons Simon hadn't cracked the 1,000-yard plateau.
The six-foot, 198-pound native of Johnstown, Pa., needs just 29 catches to break Ben Cahoon's CFL record of 1,017 career receptions.
"In order for me to exhaust my talent as a football player I felt I had to move forward," Simon said.
Once the Lions' season ended, Simon said he was open to restructuring his contract but if the team didn't want him back he'd look to continue playing elsewhere. Buono said Wednesday that he had given Simon and his camp permission to gauge interest in a potential trade.
"You have to separate the emotional side from the business side," said Simon, who has agreed to take a lower salary in Saskatchewan. "This is what is so tough, because emotionally I'm still a B.C. Lion."
Speaking at an availability in Regina, Riders GM Brendan Taman said Simon's talent and experience will help his team.
"Obviously, his on-field play speaks for itself," said Taman. "But the other thing he's going to bring is his leadership. His value to our team on and off the field is going to be immense. Geroy's got some points to prove to a lot of people he still can play. So I think there's a lot of bonuses to doing it.
"We know he's 37. We're aware of that, but (Baltimore Ravens linebacker) Ray Lewis is 37 and he's going to the Super Bowl."
Riders coach Corey Chamblin said Simon will complement Weston Dressler and be a "big veteran presence in the locker-room."
"We all know what he's done in this league, and he still has more to do," Chamblin told reporters.
"I guess everyone needs change. We all thought he would probably finish his career as a B.C. Lion, but he wanted change."
Simon began his CFL career with Winnipeg in 1999 before signing with B.C. as a free agent following the 2000 season. He received the league's outstanding player award in 2006 after registering 105 catches for 1,856 yards and 15 TDs, all career highs.
B.C. was 5-0 without Simon last year when it finished atop the West Division standings with a 13-5 record. The Lions dropped a 34-29 decision to the Calgary Stampeders in the conference final.
The deal gives the Lions a receiver with some professional experience, as well as the chance to stockpile some Canadian talent through the draft.
Harper, a 27-year-old native of Catawba, N.C., is entering his second CFL season. He had nine catches last year for 95 yards. Before joining the Roughriders last March, the Virginia Tech product spent three seasons in the NFL with Baltimore, receiving limited playing time.
"I wasn't big on giving as much as we did, but we had to get a deal done, because I wasn't going to let (Simon) go to free agency, because we wanted to get the guy," said Taman.
"So we had to do something. Harper's a good young player too and I think he'll do fine for them."
Buono said the deal was good for Taman because Simon, who is entering the option year of his two-year contract, was already signed.
"And for us, it's not worthy compensation, but it's the best compensation based on the situation that we're in," said Buono.
Simon has aspirations of becoming a coach after he retires. Buono, who does not know if he will be retired himself by then, indicated the Lions are open to hiring him.
"I might not be here when he comes back," said Buono, who is entering the second of a three-year contract. "But, I'm just saying, as an organization, they will — and they definitely should — respect what he's done."
Note: Buono indicated receiver Shawn Gore is exploring NFL options. The Lions are looking to re-sign him before he becomes a CFL free agent Feb. 15. Freeing up money to pay him more factored into the release of receiver Arland Bruce and defensive back Byron Parker last week.