We’re nearing the end in our countdown of former Detroit Red Wings general manager Ken Holland’s most regrettable free agent signings during his time in the Motor City. For those of you who haven’t gotten up to date on the list, here are the first three entries in the countdown:
No. 5 – Carlo Colaiacovo
No. 4 – Ray Whitney
No. 3 – Derian Hatcher
Number two on our countdown will go down not only as one of Holland’s worst free-agent signings, but perhaps one of the worst in recent memory by any general manager.
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Holland gave former Florida Panthers forward Stephen Weiss a rather hefty five-year contract in 2013 with the hopes that he’d be able to anchor the second line and offset the loss of Valtteri Filppula, who left to sign with Tampa Bay.
And things appeared to be off on the right track when Weiss tallied the overtime winning goal in Detroit’s second game of the season.
From then on, it was nothing short of a complete downfall. He only appeared in a total of 26 games in his first year in Detroit thanks to injuries, recording only four points. His nine goals with 16 assists in 52 games the following season were a bit better, but nowhere near the kind of production they signed him for.
The team bought out the final three years of his contract in 2015.
