#10. Patrick Marleau
During the Free Agency period in summer, 2017, Leafs fans saw plenty of optimism. Their team had just made the playoffs for the first time since 2004 in a full 82-game regular season and with stars Auston Matthews, William Nylander and Mitch Marner only going to improve, it was a special time in Leafs Nation.
As a result, as free agency hit, everyone expected the team to sign a defenseman. The offense seemed intact, but a defenseman was something the team desperately needed.
Instead, Lou Lamoriello and company decided to sign Patrick Marleau to a three-year $18.75 million contract.
Although Marleau only played out two of those three years and the team needed to trade a first-round draft pick to get out of the contract, the deal was worth it. Marleau scored 27 goals in his first year and provided a veteran presence in the dressing room that you can’t buy.
Marleau’s contract was definitely too rich by the end of it, but he was still a very good second-line player and leader that Matthews and Marner adored.