Optimism abounded in Calgary that season after the Flames eliminated the two-time defending champion Edmonton Oilers in seven games in the Smythe Division Final after defenseman Steve Smith fired a pass from behind his net that banked off goaltender Grant Fuhr and into the Oilers net, clinching Game 7 for the Flames.
That Oilers team arguably is one of the best to not win a Cup and would go on to win it all the following two seasons. Despite that confidence-building victory against the rival Oilers, Otto said the young Flames just weren't ready to perform on the biggest stage imaginable in the Final against the Canadiens. Even worse, Otto believed his team might have wasted the last, best chance for well-liked veteran Lanny McDonald to win the Stanley Cup for the first time.
"We had a good team in '86, but I think we surprised a lot of people," said Otto, whose Flames lost to the Canadiens in five games. "Basically, beating Edmonton was the Stanley Cup that year. A lot of us were new to the Stanley Cup and for me as a young player and looking at Lanny when we did lose in '86 and how upset he was kind of really hit home. It was like, 'Man, you don't get many opportunities. Hopefully we didn't blow our one and only chance.'"
Three years later, Otto and the Flames got another chance against the Canadiens, and that time they made the most of it.
The Flames not only won the franchise's first Stanley Cup but also became the first visiting team to win the Cup in Montreal. McDonald scored in the clinching Game 6, his final game in the NHL before announcing his retirement after the season.
Despite there being signs that the 1989 Stanley Cup Final -- the last one that involved two Canadian franchises -- was going to be McDonald's swan song, there wasn't a "Win It For Lanny" attitude in the locker room. But it still was special to get the 36-year-old his first Cup.
"Lanny never made it public it was his last year," Otto said. "Some guys might've had an inkling. I was naïve back then. I just played. And Lanny being the professional that he is, he was just working as hard as he can with his chance to win the Cup.
"It was gratifying winning and we were happy for ourselves and each other, but to a man, everyone was almost more happy for Lanny."
Despite the historic victory, Otto said he wasn't swept up in the accomplishment of winning the Cup in the hallowed Montreal Forum. But over the years, he's grown to appreciate it.
"My dad was a Montreal Canadiens fan, so I was kind of brought into that mix and cheered for the Canadiens growing up. As soon as I started playing, he seemed to not like them as much," Otto said. "In hindsight, it is more special now, absolutely. Obviously, everyone wants to win it on home ice with everybody celebrating with you. But as you look back on it now, and even a few years after the fact, being the first team to win it on Montreal's home ice made it a bit more special for sure."
After Game 3 of that series, however, winning the Cup anywhere against the Canadiens seemed to be a monumental task.
The Flames and Habs split the first two games in Calgary, setting the stage for a pivotal Game 3 in Montreal. In the second overtime, the Flames' Joe Nieuwendyk had a chance to get the puck out of his zone, but he turned it over at the blue line. Montreal's Stephane Richer carried the puck down low before centering to Ryan Walter, who banged the puck past Mike Vernon to give the Habs a 4-3 win and a 2-1 series lead.
The Flames responded by winning the next three games, with Vernon holding the Canadiens to two goals in each game.
"Looking back on it now, losing Game 3 like we did and being able to come back after that was something we're very, very proud of," said Otto, who had 6 goals and 13 assists in 22 games during that playoff run. "It was a tough hole to get into and a very emotional Game 3. I remember it was quite physical and a few penalties late in the game. To come back after being crushed like that, we're pretty proud of that."
"By the time we got to '89, we added some pieces to the puzzle," Otto said. "There were a lot of pieces that certainly fit into the mix. It wasn't like we were going into '89 thinking we were the same team we were in '86 and had this mental block against Montreal."
These days, the 49-year-old assistant coach with the Western Hockey League's Calgary Hitmen is gearing up for a busy weekend at the 2011 Tim Hortons NHL Heritage Classic.
The Hitmen will face the Regina Pats on Monday at McMahon Stadium, but Otto also will take part in the Outdoor Alumni Game on Saturday, when members of the Flames and Habs who battled in those Cup Finals lace them up one more time.
"We got a good group of guys coming in," Otto said. "I'm having a blast just trying to get in shape for this thing, that's been part of the fun. Just being able to be involved … it's going to be a great weekend."
Follow Dave Lozo on Twitter: @DaveLozo