Twenty years ago this month, the Senators made three decisions that helped derail the greatest team in franchise history.

The 2005-06 Senators were loaded.

They won 52 games, finished with 113 points and scored 314 goals, all franchise highs. Daniel Alfredsson, Dany Heatley and Jason Spezza were probably the best line in hockey. Wade Redden and Zdeno Chara anchored the D, and Martin Havlat provided another dynamic offensive weapon up front.

And in goal, Ottawa had one of the greatest of all time in Dominik Hasek.

Unfortunately, Hasek suffered an adductor injury while playing at the 2006 Olympics and never played another game for Ottawa.

Without him, the Senators were upset by Buffalo in the second round.

Beyond that, anything can happen in a short series, and it certainly did in that one as the Sabres won all three of the games that went to overtime. Sens fans still curse Jason Pominville, who became the first player in NHL history to score a short-handed overtime goal to end a series.

That disappointment was followed by a nine-day stretch in July when Hasek, Chara, and Havlat all left town.

The Senators reached the Stanley Cup Final the following spring anyway. But no one would ever compare the two rosters and suggest the Senators got better. 

General manager John Muckler's first major decision came on the opening day of 2006 free agency.

Rather than take another chance on the 41-year-old Hasek, who wanted to re-sign with the club, Muckler signed Martin Gerber to a three-year, $11-million contract.

At the time, the decision was understandable.

Hasek's Olympic injury (and the way it lingered) frustrated the Senators, who wanted more certainty in goal, and Muckler felt like Gerber would provide that. He had just played 60 games for the eventual Stanley Cup champion Carolina Hurricanes. 

As it turned out, despite being 10 years younger, Gerber was closer to the end than Hasek. There was a reason the 'Canes turned to rookie Cam Ward as their starter in that Cup run.

Hasek signed with Detroit and went 38-11-6 with a 2.05 goals-against average the following season, helping the Red Wings reach the Western Conference Final. One year later, he won another Stanley Cup.

Gerber, meanwhile, struggled early in Ottawa and almost immediately lost the starting job to Ray Emery.

Emery eventually helped the Sens reach the 2007 Stanley Cup Final, but it's difficult not to wonder what Hasek might have done for that team.

The same day Ottawa officially turned the page on Hasek, Chara left to sign a five-year, $37.5-million contract with the Boston Bruins.

The Senators wanted to keep both Chara and Redden, another unrestricted free agent who had just produced a career-high 50 points in 65 games. But with owner Eugene Melnyk signing the cheques, it's not hard to imagine why making both players happy was always going to be a challenge.

Ottawa retained Redden on a two-year, $13-million deal. Chara says his phone stopped ringing.

"I wanted to stay here," Chara told the Ottawa Sun that summer. "I'm very disappointed. I thought Ottawa would be really aggressive and they would really show it. In the last nine days before July 1st, we never received a phone call. Myself and (agent) Matt (Keator) were just sitting there and making all the calls. We told them, 'Let's talk and let's negotiate.' They said: 'Six million. You sign it, or we're going to go the other way.' They did.

Redden played two more seasons in Ottawa. Chara became Boston's captain, won a Norris Trophy and eventually led the Bruins to the 2011 Stanley Cup.

Knowing that the Sens would face a big, ornery Anaheim team in the upcoming season's Stanley Cup Final, it's especially difficult not to imagine what the 6-foot-9 Chara might have meant in that series.

Eight days into free agency, the Sens traded Havlat and Bryan Smolinski to Chicago in a three-team deal involving San Jose. 

The Senators wound up with Tom Preissing, Josh Hennessy, Michal Barinka and a 2008 second-round pick.

The speedy Havlat was a high-end offensive talent entering his prime. He immediately scored 25 goals and 57 points in just 56 games with Chicago.

While Smolinski was starting to fade, he had produced 48 points for Ottawa the previous season and provided valuable veteran depth. Both players would have bolstered the forward depth in that '07 Cup Final.

The Sens didn't become a bad team after losing those players. They were still an excellent club that went further in the playoffs than any other Sens team. But the fact remains they were a lesser team. You could start to see it during the regular season when they dropped from 113 points to 105 and from 314 goals to 288.

Would Ottawa have beaten Anaheim if Hasek, Chara, and Havlat were still around? We'll never know for sure, but they would have, unquestionably, had a better chance. 

20 years later, that's part of what makes July 2006 so fascinating... and maybe a bit haunting as well.

By Steve Warne
The Hockey News