They have not been too bad in the first round, but mainly because of an abundance of top 5 picks. Since I started watching in 2002, they took:
2003 Pouliot
2004 Dybnyk and Schremp
2005 Cogliano
2007 Gagner
2008 Eberle
2009 Pajarvi-Svensson
2010 Hall
2011 RNH and Klefbom
2012 Yakupov
2013 Nurse
2014 Draisaitl
2015 McDavid
2016 JP
2017 Yamamoto
2018 Bouchard
2019 Broberg
2020 Holloway
2021 Bourgault
2022 Schaefer
In 20 years one
1 generational player (McDavid)
2 star players (Draisaitl, Bouchard)
4 impact players (Hall, RNH, Nurse, Klefbom).
4 solid NHLers (Dubnyk, Cogliano, Gagner, Eberle)
1 meh NHLer (Yamamoto)
2 showing considerable promise (Broberg, Holloway)
5 busts (Pouliot, Schremp, PS, Yakupov, JP)
2 remains to be seen (Bourgault, Schaefer)
I guess 5 busts in 20 years is not that much, but some really hurt this team.