Top 5 Worst Toronto Maple Leafs Free Agent Signings of All Time

5. Tim Connolly

2 year $4.75M AAV CH: 7.4%

In the 2011 Free Agency, the Leafs were in need of adding some depth to their forward group, specifically up the middle.

Their top two centers at the time were Tyler Bozak and Mikhail Grabovski. Enter; Tim Connolly who had been a high-scoring top-six center on a cup contender in recent years, scoring at a near point-per-game pace in three of the previous four seasons.

His bread and butter was his playmaking ability which should have paired well with one of the Maple Leafs’ high-scoring wingers like Phil Kessel and/or Joffrey Lupul.

The problem with Connolly was that he had a long and well documented history of injury troubles. He missed the entire 2003-04 season due to post-concussion syndrome, and all but two regular season games and the playoffs in 2006-07.

He also missed 35 games each in both 2007-08 and 2008-09. Over the two seasons before coming to Toronto, he missed 24 games in total. 

To nobody’s surprise, the contract unfortunately blew up in GM Brian Burke’s face.

Despite playing 70 games in 2011-12, he produced at the lowest rate in years scoring only 13 goals, 23 assists for 36 points.

The following year was the NHL partial season lockout. After the NHL returned to action, he was put on waivers and Connolly was assigned to the Toronto Marlies where he played 28 games and produced 12 points. When his contract expired he announced his retirement from the league at the age of 32. It is unfortunate that things did not work out for Connolly and it is always sad when players careers are cut short due to injuries.

Due to the deal being short term and having a lower caphit percentage than most contracts ahead of him on this list, it lands at number five.