The absolute pinnacle of "drafting against the grain" is General Manager Doug Wilson of the San Jose Sharks. San Jose's strategy since the 2000 draft has been abundantly clear and abundantly strange. In the nine years between 2000 and 2008, San Jose drafted 12 goalies exclusively in the middle rounds or later. The earliest pick was Tyler Sexsmith in 2007 who was drafted early in the fourth round. To make matters even more strange, four of the 12 goalies were Germans playing in the Bundesliga. Thomas Greiss, a German, taken early in the fourth round in 2004, is the only goalie yet to pan out and it appears the Sharks have abandoned the practise and haven't taken a goaltender since 2008. Patterns like this are interesting and fun to follow, but other teams have patterns that have worked out better than San Jose's and it's worth examining what they were up to in the most recent drafts.
Most people are aware of Detroit's European Scouting (largely Hakan Andersson) so I'll touch on it briefly. Detroit has almost single handedly stolen Europeans from the mid and late rounds dating back to Tomas Holstrom (257 overall) in 1994. In 1998 Pavel Datsyuk was taken 171st overall and Henrik Zetterberg was taken 210th overall a year later. The most interesting selection was Jonathan Ericsson, the last player taken in the 2002 draft who has provided solid defense for Detroit for two seasons. Tomas Fleischmann and Valtteri Filppula were taken in the third and fourth rounds in the same draft. Add solid prospects Gustav Nyquist, 121st overall in 2008 and Teemu Pulkkinen, 111th in 2010 and it makes good sense to keep an eye on two of Detroit's later picks this season - Mattias Backman, 146th overall and 205th overall Alexei Marchenko.
Buffalo has also been successful at the draft mainly out of necessity. Sabre stars Daniel Briere, Chris Drury and Bryan Campbell have all left Buffalo at the peak of their careers for bigger paydays elsewhere. Buffalo's "against the grain" strategy has been to mine the QMJHL for prospects and have drafted more players from the "Q" than any team in the NHL. Between 2000-2010, Buffalo drafted 17 players from the "Q" whereas Montreal have drafted only 16 players from a league in their own back yard. The rewards have been veteran forward Jason Pominville, Marc-Andre Gragnani, their leading playoff scorer last season, and prospects Luke Adam, Paul Byron and T.J. Brennan.
Since Buffalo is the leading organization in scouting the QMJHL, you might want to take a second look at defenceman Jerome Gauthier-Leduc (68th overall in 2010), and winger Cedrick Henley (173rd overall in 2010) who may have been overlooked by other organizations.
The Montreal Canadiens take a similar approach to Detroit and are able to mine the later rounds for European talent. Like Detroit, Montreal has an elite scout leading the way. Trevor Timmins, Director of Procurement and Player Development, has overseen the last 10 drafts and has done wonders picking up Europeans in the later rounds. The biggest steal was Jaroslav Halak, taken 271st overall in 2003. Montreal also nabbed Tomas Plekanec 71st overall in 2001, Mikhail Grabovski 150th overall in 2004, and Sergei Kostitsyn, 200th overall in 2005.
In 2006, Pavel Valentenko was a steal at 139th overall but returned to Russia for family reasons. Prospects Alexander Avtsin (2009, 109th), Alexei Emelin (2004, 84th) and Joonas Nattinen (2009, 65th) are still considered blue chippers so a good look at Montreal's later rounds in the last draft is in order. Don't forget the names Magnus Nygren (113th overall) and Daniel Pribyl (168th overall). Timmins has done it before and he'll do it again.