It was after the 2002 season when he joined Wally Buono in making the move from the Calgary Stampeders to the B.C. Lions. Two off-season decisions made by the new brass then were to acquire quarterback Dave Dickenson and deal 39-year-old veteran Damon Allen to the Toronto Argonauts.
But the move came back to haunt O'Billovich and Co., when Allen led Toronto past B.C. in the 2004 Grey Cup.
So age never was a consideration Tuesday when O'Billovich, now the Hamilton Tiger-Cats general manager, acquired quarterback Henry Burris from Calgary for veteran passer Kevin Glenn, offensive lineman Mark Dewit and a conditional draft pick.
Burris will be 37 by the time the 2012 season gets underway.
"Damon went to Toronto and made them better and ended up beating us in the Grey Cup," O'Billovich said with a chuckle. "Guys like Damon Allen and Henry Burris take care of their bodies and work hard in the off-season to stay in top shape.
"Those kind of guys when they get older have to think younger if they're going to be able to perform at a high level and Henry is one of those kind of guys. If he wasn't, I might not have been as excited about doing this as I was. He's ready to do what he has to do to help us win football games."
Then again, Montreal's Anthony Calvillo will turn 40 this year and is coming off a 2011 campaign that saw him lead the CFL in passing and become pro football's all-time passing leader.
Both Hamilton and Calgary confirmed the trade Tuesday but it was hardly a surprise. News broke of the transaction late Monday.
The move ends months of speculation regarding Burris' future in Calgary after he lost his starting job to backup Drew Tate late last season.
It became clear last week the six-foot-two, 219-pound Burris' days in Alberta were numbered after Calgary signed Tate to a long-term contract extension.
The move is a homecoming for Dewit, a Calgary native who played at the University of Calgary.
Calgary finished tied with B.C. and Edmonton for the CFL's best record at 11-7. But the Stampeders were relegated to third in the West Division after losing the season series to the Lions and Eskimos, then ended the campaign with a 33-19 semifinal loss to the Esks.
Burris, the CFL's outstanding player in 2010, was in his second stint with the Stampeders and spent a total of nine seasons there. He is Calgary's all-time leader in passing yards (32,171), touchdowns (233), attempts (3,677) and completions (2,167).
John Hufnagel, the Stampeders' head coach and GM, said it was tough to deal Burris.
"I'm a big fan of Henry Burris, he knows that," he said. "He knows sometimes things happen and people move on.
"This is a new lease on life for him and I wish him nothing but the best. It will be strange not seeing No. 1 on the football field in red and white.
A 13-year CFL veteran, Burris ranks seventh in all-time passing yards with 41,235. He has also rushed for 4,392 yards and 55 TDs and captured two Grey Cups, being named the MVP of Calgary's win over Montreal in 2008.
Burris remains one of the CFL's best when he's on his game. Not only does Burris have a strong throwing arm, but his mobility makes him a double threat to also run.
But what excites O'Billovich most is Burris working with a young Hamilton receiving corps anchored by Chris Williams, the CFL's top rookie last season.
"What Henry brings that gives us more optimism is he's more athletic, he's been there before and knows how to win," O'Billovich said. "But I know he's pretty excited about the prospect of teaming up with our young receivers and can see where it could be a mutual thing to really have some fun."
While he's solidified his quarterback corps, O'Billovich's off-season work isn't done. He still has to hire a head coach to replace Marcel Bellefeuille, who was fired in November.
O'Billovich has secured permission from the NFL's Buffalo Bills to speak with quarterbacks coach George Cortez, a former longtime CFL offensive co-ordinator. O'Billovich said he has yet to talk to Cortez, but intends to do so very soon.
Glenn, 32, opened the season as Hamilton's starter but ended up splitting the starting duties with late in the year with backup Quinton Porter as Hamilton finished third in the East Division standings with an 8-10 record. But the Ticats dispatched Montreal in the conference semifinal before losing to Winnipeg in the final.
Hufnagel said Tate will enter training camp as the starter but Glenn will be given the opportunity to compete for the No. 1 job.
"We do have a pecking order to start training camp as far as a depth chart," he said. "But then competition on the field is going to say who plays.
"I know the quarterback position is ultra sensitive and I'll take that into consideration."
Glenn said all he wants is the chance to compete.
"I don't think it will be similar to the situation in Hamilton where there's uncertainty of whether or not you're going to play or how long you're going to play but still be named the starter," he said. "That takes a toll on a player.
"I loved my stay in Hamilton, I had a great time there . . . but for (Calgary) to trade for me I've been accepted by the team already. Having the opportunity to go into camp to compete makes everybody better and that's all you can ask for."
Calgary will become Glenn's fourth CFL stop. He began his career in Saskatchewan before heading to Winnipeg, where he helped lead the Blue Bombers to the 2007 Grey Cup. But he didn't play in the title game after suffering a shoulder injury in the East Division final.
Over his 11-year CFL career, the five-foot-10, 205-pound Glenn has passed for 32,446 yards with 179 touchdowns and 128 interceptions.
The six-foot-three, 305-pound Dewit became Hamilton's starting centre late in the season after incumbent Marwan Hage suffered a knee injury. Dewit was a 2008 sixth-round draft pick of the Toronto Argonauts.