From 1998 to 2006, ten draft years, here are the first round goaltenders:

Patrick DesRochers
Mathieu Chouinard
Brian Finley
Maxime Ouellet
Ari Ahonen
Rick Dipietro
Brent Krahn
Pascal Leclaire
Dan Blackburn
Jason Bacashihua
Adam Munro
Kari Lehtonen
Cam Ward *** won Cup
Hannu Toivonen
MA Fleury *** won Cup
Al Montoya
Devan Dubnyk
Marek Schwarz
Cory Schneider ***  won Cup...just joking! 
Carey Price
Tuukka Rask
Jonathan Bernier
Riku Helenius
Semyon Varlamov
Leland Irving

10 years, 25 goalies, two Cups.

And before you cry that I was cherry picking, 10 years is a decent sample size.  I stopped in 2006 because anyone since then hasn't had a chance to make an impact.

This is a throw away pick for the Bruins and Chiarelli should be embarrassed about it.