I should preface this by saying that I typically like Kevin Lowe as a general manager. The organization's scouting and player development have improved leaps and bounds since he was installed as general manager in the summer of 2000. He's added some nice, underrated pieces through free agency (Staios, Garon), and he's won more than his share of trades.
That said, he has a horrible tendency to make the occasional colossal mistake, the kind of mistake that undoes half a dozen good moves. The Sheldon Souray contract is frequently cited as Kevin Lowe's biggest error, but it wasn't. Neither were his transactions with Anaheim - the Pronger trade, the Penner offer sheet. No, in terms of absolute stupidity, Kevin Lowe's greatest error was one that had virtually no impact on the franchise.
The Thomas Vanek offer sheet.
The highly skilled Austrian is an easy character to forget about, given that the RFA offer sheet was matched by Buffalo GM Darcy Regier, but it really doesn't mean that Kevin Lowe should be let off the hook.
The dollar figure was the first ridiculous amount. 50 million dollars over 7 years was a big, upfront contract that was paying for potential, with little hope of being fair compensation for value received until years three or four of the deal. In fairness, Vanek is a young forward who has a good chance at being an upper echelon guy for some time to come. But the dollar figure alone wasn't the worst part of the deal.
Four 1st round draft picks would have been the compensation that Buffalo would have received from the Oilers, a compensation that would be too high, unless Sidney Crosby was the player coming the other way. We can't say who those players would have turned into, but looking back, we can see the guys Edmonton has selected. The last four 1st rounders that Edmonton selected were Jordan Eberle, Sam Gagner, Andrew Cogliano, and Devan Dubnyk. The other four selected under Kevin Lowe were Rob Schremp, Marc Pouliot, Jesse Niinimaki, and Ales Hemsky. In each group, at least one player (Gagner, Hemsky) turned out sufficiently that Lowe would have rued the exchange.
The problem, in my mind, stemmed from a palpable desperation coming from Lowe's office at the end of 2007. Spurned by a whole bunch of free agents, facing a backlash from fans after the Ryan Smyth trade, unable to do anything to address the nosedive the Oilers had gone into to finish the season, Lowe was in a bad situation. I think that he acted desperately, willing to take foolish risks to try and right a ship had capsized. The summer of 2007 is now clearly the low-water mark for Kevin Lowe as a general manager, a comedy of errors that could have turned out much worse. Sheldon Souray and Dustin Penner were not great, or arguable, even particularly good acquisitions, but the offers made to Nylander and Vanek would have been even more disastrous.