Top 10 Worst Trades in Toronto Maple Leafs History

Toronto Maple Leafs goaltender Andrew Raycroft makes a blocker save as Boston's Wayne Primeau looks behind him for a rebound during game between the Toronto Maple Leafs and Boston Bruins at the Air Canada Centre in Toronto, Canada on November 28, 2006. (Photo by Jay Gula/Getty Images)
Toronto Maple Leafs goaltender Andrew Raycroft makes a blocker save as Boston's Wayne Primeau looks behind him for a rebound during game between the Toronto Maple Leafs and Boston Bruins at the Air Canada Centre in Toronto, Canada on November 28, 2006. (Photo by Jay Gula/Getty Images)
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Toronto Maple Leafs
Toronto Maple Leafs

ST PAUL, MN – JUNE 24: 22nd overall pick Tyler Biggs by the Toronto Maple Leafs  . (Photo by Bruce Bennett/Getty Images)

#3. Leafs Take “Biggs” Swing and Miss

The Trade:

  • Toronto Maple Leafs acquire: 2011 1st Round Pick (Tyler Biggs)
  • Anaheim Ducks acquire: 2011 1st Round Pick (Rickard Rakell) and 2011 2nd Round Pick (John Gibson)

Ughh, how many times do we have to visit this trade? Every time I talk about it, I cringe. How could a trade like this actually happen?

Let’s break it down like this:

  • Tyler Biggs: 
    • 0 NHL Games Played
    • 0 career goals, 0 career points
    • Fun Fact: Scored a career-high 18 goals in the East Coast Hockey League and at 27-years-old doesn’t play professional hockey anymore
  • John Gibson:
    • 287 NHL Games Started
    • 2.53 GAA, 0.918 Sv %, 139-103- 33 record
    • Fun Fact: 2015-16 William Jennings Trophy winner
    • Rickard Rakell
      • 447 NHL Games Played
      • 129 Goals, 283 Points
      • Fun Fact: Two-Time 30 Goal Scorer
      • Do I really need to say anything else? When you move two draft picks for one, you better select a great player. Instead, the team moved on from a 30-goal scorer and starting NHL goalie for a nobody.

        I know this is third-worst on this list, but in 10 years, it could be number-one if Rakell and Gibson continue to have great NHL careers.