I think one of the big reasons they haven't been as successful is because they didn't really change the make up of their teams over the years. The only changes Edmonton really made was inserting the 1st overall pick into the lineup, handing them top minutes. And when one of your top, if not top player(s) are young guys who will obviously make mistakes as they learn the NHL, it almost becomes allowed to make mistakes and be okay with not always winning.
Burke with the leafs was constantly trying to improve the team. We had a chance to give up when we traded Kaberle for picks + futures. But instead we took one of the picks and traded for Liles, shows a vote of confidence in the team saying 'we aren't giving up yet'. We had a weakness (and still do
) down the middle, we could've folded and just try again later, but instead we went out and signed Connolly showing that the team is still trying to win. Same goes with other UFA signings such as Armstrong, Komisarek and Gustavsson. Did they work out with their play? No. But they did bring the attitude of we aren't giving up, we are going to go out there and try to win games. Another example of always trying was trading for Kessel. Nothing says I won't tolerate losing like giving up the next 2 years first round picks (we did still lose
but it brought the attitude that we are going to go down trying).
I look at Colorado as another example of this. They signed PAP. They traded their first for Varlamov (which was pretty ridiculed at the time because many thought it could end up being a lottery pick). They brought in Tanguay. And now they are one of the best teams in the league.
I like how a team like Edmonton is doing things now. Bringing in Bryzgalov. Signing Gordon. Putting lots of money on the table for Clarkson. Trading some futures for Perron. These are the kind of moves I think you need to make even during your losing years. I like a lot of the moves Edmonton has made recently. Only question, is it too late?