I wouldn't say that they're the worst drafting team at all. Almost no one won out of the '99 draft save St. Louis and Ottawa with Jackman and Havlat respectively in the 1st round. From 2000-2002 they had top 3 each time and since then they've only had 3 years in which to draft "smartly".
Although no one will believe me, I was saying that Phaneuf should've been the 1st defenceman to go in '03, but Coburn was a fine selection and should be a superb no. 2 for years to come. IMO it will be pretty hard to find a bad pick in the 1st round of '03 (although I think Carter will make a fine case in three years
) but they still came out winners. '04 and '05? There's no point in discussing it (though Wolski, Radulov and Meszy would have been better in '04 right now) becuase you can't determine boom/bust at this point.
Drafting "smart" sometimes has a lot to do with luck and willingness to take a risk. In Ottawa's case, Igor Mirnov could either become the next Brad Richards or the next Igor Radulov (in terms of NHL success NOT in style of play of course). Havlat could've easily become Mikhail Kuleshov. "Smart" drafting requires big
cajones and luck has a part in determining how a player will develop.