4. Nikolai Khabibulin (the second time)
Nikolai Khabibulin was a big free agent signing for the ’Hawks going into the 2005-06 season. He was just coming off of a Stanley Cup championship in 2004 with the Tampa Bay Lightning. He dealt with injuries and ineffectiveness during the latter days of the dark ages of the ’Hawks.
This signing would be a huge bust if he hadn’t helped lead the ’Hawks to the 2009 Western Conference Finals. So, basically Khabibulin came close to being on this list twice! After the 2009 season, Khabibulin signed with the Edmonton Oilers and watched his career hit the skids, with injuries and off-ice trouble.
After the 2012-13 season, Khabibulin was a 40-year-old free agent and was contacted by Bowman. Khabibulin signed a 1-year contract to be Corey Crawford‘s backup for the 2013-14 season, while Antti Raanta got familiar with North American hockey while playing for Rockford in the AHL.
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Things didn’t go exactly as planned …
Khabibulin played like a man in his fourth decade of life. After four disastrous games where Khabibulin complied an .811 save percentage and a 5.00 goals-against average, he was put on injured reserve, which wound up ending his career.
The ’Hawks would then prematurely call up Raanta, who played well, but clearly had his development stunted. He ultimately lost the backup goaltender job this past season to Scott Darling, which ended up working out very well in the first round of the 2015 playoffs, en route to the Stanley Cup. So, perhaps this was one lucky blessing in disguise.
Spoiler alert: This is the only Stan Bowman signing on this list.
Next: Third-Worst Free Agent Signing