The 2008-2009 NHL season was a historic one for the Montreal Canadiens. The team was celebrating its 100th season in the league. Many people around the hockey world were predicting that they would win the East after finishing first place the season before. If fans alike wanted to see a 25th Stanley Cup parade happen on Rue Saint-Catherine that year, they obviously needed to get bigger as they were clearly outplayed physically when they lost to the Flyers in the second round. Montrealers did not get the wish they wanted as they were eliminated in four straight games by arch-rival Boston. Even though the GM at the time Bob Gainey tried to address this need during the offseason, he should of thought of something else that would have greatly benefited them for the upcoming season.
That offseason, it was widely rumored that the Canadiens were going to land the aging yet productive big first line centre Mats Sundin as they had exclusive negotiating rights. Sundin decided to sit out for the beginning of the season and eventually join the Vancouver Canucks in late December. This led to Gainey having to go to Plan B and acquiring Robert Lang from the Blackhawks. Although he only played in 50 games, he proved to be a good fit as he managed to score 39 points in his role.
So if Bob Gainey did in fact sign Jaromir Jagr during that offseason, would it have made a difference? The simple answer is yes but at the same time no. The reason behind it is even though Jagr had the size and scoring touch, the Habs would have still not won the cup that year based on the fact that they were still a small team which made easier for teams like the Bruins, Flyers and Penguins to beat them based on playing a more physical style of hockey.