The 17-year veteran quarterback signed with the Edmonton Eskimos on Monday. The CFL said that makes Glenn the only player in its history to have had his rights held by all nine franchises.
Glenn envisioned achieving the milestone by signing a one-day contract with Edmonton, then retiring. But the 38-year-old Detroit native will provide depth behind incumbent Mike Reilly, the CFL's outstanding player last season.
"I didn't think it would come about like this,'' Glenn said with a chuckle during a telephone interview. "But it's a much better feeling this way.
"The way I joked about it wasn't legit, it was to make the cycle complete. This is legit.''
Glenn hasn't played for every CFL team. He was with the Ottawa Redblacks and Toronto Argonauts but was traded by both clubs before ever suiting up.
He played three separate times with the Saskatchewan Roughriders (2001-03, 2015, 2017) and twice for the Winnipeg Blue Bombers (2004-08, 2016).
Glenn fills a need for Edmonton, which dealt the rights to backup James Franklin to Toronto earlier this off-season for a 2017 second-round pick and Canadian offensive lineman Mason Woods. Franklin later signed a two-year deal with the Grey Cup-champion Argonauts.
Edmonton (12-6-0) was third in the competitive West Division last year before downing Winnipeg 39-32 in the conference semifinal. But the 2015 Grey Cup champions' season ended with 32-28 loss to the Calgary Stampeders in the division final.
Glenn has never won a Grey Cup but has high hopes for the Eskimos.
"They're pretty good,'' Glenn said. "To be approached by a team like that says they're looking for a couple more pieces they think they need in order to get to that next point.
"I can help them get there.''
Reilly is firmly established as Edmonton's starter but Glenn said he doesn't have to be playing to contribute.
"You need more than one quarterback and I think everyone in this league understands that,'' Glenn said. "Sometimes people don't see or talk about it but behind the scenes, especially as a starter, being able to come to the sidelines and get insight on what's going is valuable because you don't know it all and don't always see it all.
"When you've got guys on your team who can help you do that, it just makes your life a lot easier.''
Glenn threw for 4,038 yards and 25 touchdowns last year with Saskatchewan, helping the Riders reach the East Division final. He has appeared in 268 career regular-season games and stands sixth in CFL passing yards (52,867) with 294 career TDs against 207 interceptions.
Saskatchewan released Glenn after acquiring Zach Collaros from the Hamilton Tiger-Cats. But the veteran quarterback didn't spend much time feeling bad - he was en route to Miami for a friend's 40th birthday party when he got the news.
"I didn't have time to sulk and dwell on what Saskatchewan did,'' he said. "But there is a silver lining when you make history and sign with a team you feel is pretty darn good and has a shot to go out and win it all this year.''
Glenn's historic achievement, though, could be short-lived. A group in Halifax is looking to bring a CFL expansion team to the Maritimes possibly by 2020.
"Now, we might have to be coming out of retirement to sign that contract if that happens,'' Glenn said. "If it's 2020 or 2021, my wife will have made me retire by then.''
(Canadian Press/Dan Ralph)