Former Detroit Red Wings general manager Ken Holland was once highly regarded as one of the top executives in the National Hockey League. Winning the Stanley Cup three times as GM with several division titles and Presidents Trophies as the NHL's top team are hard to argue.
But fans believe that he was soon exposed in the salary cap era when the open checkbook of Mr. Ilitch was a thing of the past. While he made several re-signings that later proved regrettable, we'll be counting down the top five free agents that he brought to the Motor City from elsewhere that – to put it nicely – just didn't work out. Here's number five on the countdown:
No. 5 – Carlo Colaiacovo
The oft-injured defenseman was brought aboard by Holland in 2012 with a two-year pact following the retirement of Nicklas Lidstrom and the subsequent striking out on prized-free agent Ryan Suter. While he was never considered to even coming close as a replacement for the greatest defenseman of all time, Colaiacovo was expected to bring a veteran presence to Detroit's blue line and provide some stability.
He suffered a shoulder injury in just his second game with the team and missed the next 33 games during the lockout-shortened 2012-13 Season. He would appear in nine of Detroit's 14 playoff games, registering an assist. He was given a compliance buyout on the second year of his deal following the season, ending an uneventful year in the Motor City.