By Michael Farber

The five-year plan ultimate didn't work any better for Bob Gainey than it did for Soviet wheat.

You see, this was how it was going to work in the city that still believes in hockey fairy tales. Gainey, with one Stanley Cup as a general manager in Dallas, would remake the once-proud Montreal Canadiens one year at a time with draft picks and judicious trades and signings. With the hockey gods' permission, in five seasons -- culminating in the team's centennial of 2008-09 -- the Canadiens would reaffirm their birthright by winning the Cup and throwing those fabulous made-in-Montreal parades.

And then everyone was going to live happily ever after (or at least until the power play went 0-for-16 the following season). The end.

Well, five seasons turned into six with almost nothing to show for it. There was a surprisingly strong run in 2007-08 when the Canadiens were the best team in the Eastern Conference during the regular season -- and seemingly poised to mount the next step the following year, right on schedule -- but they faltered in the 2008 playoffs and barely qualified in 2009. Considering how Boston brushed them aside last April like a man picking lint off his blue suit, you almost wonder why the Canadiens even bothered.

With the team now on the far side of the mountain after the failure of his first five-year plan, Gainey had no choice but to begin a new one. It included a stunning summer during which he did not re-sign any of his 10 unrestricted free agents and looked elsewhere to stockpile skilled but pint-sized forwards who are better suited to battling Gulliver than the elite teams in the conference. Montreal's financial flexibility vanished in the blink of an eye with the signings of Brian Gionta (five years for $25 million, as Gainey essentially outbid himself), Mike Cammalleri (five years, $31 million), and his taking the rest of Scott Gomez's absurd contract (another five years, $33.5 million) off the hands of the grateful New York Rangers.

Like the gift that keeps on giving, those astonishing contracts can now bedevil Gainey's interim successor, assistant Pierre Gauthier, who managed Ottawa and Anaheim in the pre-salary cap era.

The profligacy that took the Canadiens to the cap for 2009-10 (and the financial box for the next five years) ultimately might not have sat well with the new Montreal ownership fronted by Geoff Molson of the brewery family. Gainey already had saddled them with coach Jacques Martin, a safe but hardly inspired choice. The Molson group, which had not yet formally taken control of the Canadiens -- a franchise that had been part of its family business between 1957 and 1971, and again between 1978 and 2001 -- was essentially guaranteed a bubble playoff team for as far as the eye could reasonably see.

Still, the resignation on Monday was Gainey's choice. He said he didn't want to remain in the job after his contract expired following the season. After a difficult period of reflection, and with the trade deadline looming on March 3, he decided "to pass the torch" now. When asked what he will do with his time -- beyond his role as a special advisor to Gauthier -- Gainey said he wasn't quite sure. Maybe, he said with his inscrutable smile, he'd learn to play the piano.

Gainey's costly summer was just the landmark moment of a tenure that began in 2003. There were underlying and revelatory themes, constants that marked a tenure in which the franchise brand recovered -- book it: a sold-out 21,273 fans per game -- but the hockey team often seemed to be skating into a 20-mile-per-hour headwind.

Here are four:

Mediocre scouting.

While Montreal's amateur scouting has been constantly scrutinized because of the inability to hit a first-round home run -- the jury is still out on 22-year-old goalie Cary Price, drafted fifth overall in 2005 -- its pro scouting under Gainey was far more problematic. The Canadiens routinely erred in their evaluations of NHL players. Indeed in the past decade there might not have been a more lopsided player-for-player deal than Mike Ribeiro for Janne Niinimaa when Gainey settled for an end-of-the-line sixth defenseman in exchange for a player poised to become a No. 1 center in Dallas. (Although Ribeiro was viewed as a stray cat in Montreal, Gainey conceded last year that the trade truly was horrible.)