Umm...
Shea Weber
Kevin Klein
Roman Josi
Nick Spaling
Magnus Hellberg
Adam Hall
Not bad at all, IMO. Much better lately too, he's improving.
I was referring to forwards, but since you mention it...1999 for example, yes, we drafted career fringe NHLer Adam Hall--but we had 5 second round picks that year. Aside from career AHLer Andrew Hutchinson, most never sniffed the NHL.
2000? Daniel Widing. "Talented" swedish forward never even played a complete season in north america.
2001 Timofei Shishkanov(bust) and Tomas Slovak(no NHL games)
2003- As you mentioned, Klein and Weber-- how about Glazachev over David Backes or Patrice Bergeron?
2006- a reach pick for a local, "feel good" story for Blake Geoffrion, who, even before his injury, was panning into a fringe NHL bottom six forward. Could have had Brad Marchand, who was rated higher at the time, but had to go off the board to grab the Brentwood kid.
2007- Jeremy Smith (AHL goaltender\possible NHL backup) and Nick Spaling (useful third liner) instead of Wayne Simmonds
2009- yes, a good draft for Nashville, though the second round is...surprise, iffy. Budish-- okay prospect, projects as a utility forward\bottom six. Charles Olivier Roussel - hasn't developed as expected, struggled to hold an AHL job this year. Passed on three players that are some of the top prospects in their respective systems--Richard Panik, Tomas Tatar, Jeremy Morin. We'll mention the first round-- Ryan Ellis is looking like an "okay" pick. Third pairing\PP specialist that has yet to put up points at the NHL level. Passed on Nick Leddy(established second pair d on the best team in the NHL) and Dmitri Kulikov(rising star).
2011- Yes, we took a goaltender that looks promising. He will also likely never play as a starter for us, given that Pekka is signed for six years. Passed on Brandon Saad to get him. Later in the round took a guy that Poile described as a "Jordin Tootoo" type in Miika Salomaki. Offensively limited checker...passed on one of Ottawa's top prospects in Shane Prince.
I can give credit where it's due...from rounds 4 on, David Poile and company are money...but as I said, when it comes to picking forwards in the second round, it's alarmingly rough. It was that way in Washington, too.