Debating the best of anything in sports is as old as sports itself.
A consensus will never be reached, but that doesn’t stop the debates from raging on.
If you ask recent Riders’ Plaza of Honour inductee Weston Dressler what generation of Saskatchewan Roughriders football is the best, he will not mince words.
“I might be biased,” Dressler said at his Plaza of Honour press conference this week. “But I feel like our era was one of the best.”
On the surface, that might be hard to believe but even if Dressler is admittedly biased, his era of Riders football might be the best in team history.
The Roughriders have won four Grey Cups and been to the championship game 19 times since their founding as the Regina Rugby Club in 1910. Saskatchewan did not win their first Grey Cup until 1966, their first trip to the title game since 1951, and did not win their second until 1989. Between 1966 and 2006, the Riders made the Grey Cup just six times in 40 years.
But things started to change in 2007, the year before Dressler arrived in Riderville.
The Riders won their first championship since 1989, beating the Winnipeg Blue Bombers 23-19 in the 95th Grey Cup in Toronto in 2007. That began a run of three championship game appearances in four years, with the team returning to the big game in back-to-back years in 2009 and 2010.
Those games didn’t end the way the team or its fans wanted — 2009 being especially heartbreaking — but there was no denying the team had become one of the premier franchises in the CFL after years of being a laughingstock.
A dip in 2011 came when head coach Ken Miller, one of Dressler’s fellow 2022 Plaza of Honour inductees, stepped aside and handed the head coaching reins over to long-time CFL assistant Greg Marshall.
The Riders got off to a horrible start that season, beginning the campaign 1-7 before Marshall was fired and replaced with the returning Miller, who was serving as vice president of football operations at the time. The change to Miller helped initially, but the Riders finished a dismal 5-13 the year after their second straight West Division crown and missed the playoffs for the first time since 2001.
The team bounced back in 2012, making the playoffs under first-year head coach Corey Chamblin but lost in the West Semi-Final to the Calgary Stampeders. Then came 2013.
After a fabulous 8-1 start, a late-season swoon saw the team lose six of their final nine games and slink into the playoffs at 11-7.
After a tight win in the West Semi-Final over the B.C. Lions, the Riders demolished the Stamps in the West Final and set themselves up to do something no other Riders team has ever done: win the Grey Cup on home soil.
Win they did, capturing the franchise’s fourth championship with a 45-23 pummelling of the Hamilton Tiger-Cats in front of their delirious hometown crowd.
After a fantastic start to the 2014 season, it looked like the party on the prairies was going to continue. The Riders looked poised to win back-to-back championships for the first time in team history before the wheels fell off during that year’s edition of the annual Banjo Bowl clash between themselves and the Blue Bombers.
Star quarterback Darian Durant was lost for the season in that game due to an elbow injury and the Riders managed to win just two of their final eight games in the regular season, before bowing out in the playoffs to Edmonton.
The following season was even worse. Durant ruptured his Achilles in Week 1, the team lost their first nine games and fired the coach that won them the Grey Cup just two years prior. The Riders would finish the 2015 season a league-worst 3-15.
Dressler’s final game in green and white came during that lost 2015 season, a meaningless Week 20 contest against the Montreal Alouettes. Despite being one of the team’s stars for close to a decade, Dressler finished his final game with just two catches for 13 yards. But he did find the end zone on both his receptions in Saskatchewan’s 30-24 overtime win, including the game-winner on the team’s first drive of overtime. One last little bit of Dressler magic for the Riders faithful.
Before the start of next season, new head coach Chris Jones released Dressler, who would go on to finish his career with a mostly unremarkable three-year stint in Winnipeg before retiring in the summer of 2019.
While Dressler’s time with the Riders ended ignominiously, the highs of his era were extremely high. While he wasn’t there in 2007, the Riders from that year until Durant’s injury midway through the 2014 season were perhaps the league’s best team.
While fans will always fondly reminisce about the days of Ron Lancaster and George Reed or Ray Elgaard and Dave Ridgeway, it is hard to argue with Dressler that his era of Riders football isn’t the best in team history.