2009 – Dylan Olsen
In Stan Bowman’s first year as the Blackhawks’ GM, he drafted Dylan Olsen with the ‘Hawks 28th overall draft pick in the 2009 NHL Draft. Olsen would go on to play 28 games with the Blackhawks in the 2011-12 season while registering just one assist with the team.
Bowman’s first pick with the team would go on to play 3 seasons with the Florida Panthers, ultimately deeming his first pick a dud. However, he did draft Marcus Kruger in the 5th round in 2009, so I guess things find a way of working themselves out.