9. Bob Gainey
The Canadiens selected Ryan McDonagh with the 12th overall pick in 2007, 10 spots before current captain Max Pacioretty. Interestingly enough, the Habs second round pick in 2007 was PK Subban. Had the Canadiens held on to their prospects, their top two defensemen would be Subban/McDonagh, and would most likely one of the deadliest pairs in the league.
Montreal ultimately traded McDonagh, along with forward Chris Higgins and prospects Doug Janik and Pavel Valentenko to the New York Rangers in exchange for Alaska native Scott Gomez, forward Tom Pyatt and prospect Michael Busto.
Gomez was the centrepiece of the entire deal and, admittedly seemed like an exciting acquisition at the time. He was just two seasons removed from a 70-point campaign and had scored 60 or more points in four out of the five seasons prior to the trade. The Canadiens were hoping he would be able to rediscover his 33-goal form from the 2005-06 season where he totalled 84 points. Boy were they wrong.
Gomez was completely unable to replicate the offensive production he displayed during his time with New Jersey and New York. He was acquired just two years into a seven-year deal that paid him over $7 million annually and did not even come close to living up to that salary. He scored a grand total of 21 goals in the three seasons he spent in Montreal, which means he got paid approximately $1 million per goal scored.