Arguably the Worst Trade in Maple Leafs History Occurred on this Day Back in 2006

Trading away a young prospect is one of the biggest crapshoots in the sport because you truly don't know if they'll ever reach their true potential, but if they do, you might look pretty foolish a couple of years down the road.

That's exactly what happened to the Toronto Maple Leafs nearly 20 years ago when they traded goaltending prospect Tuukka Rask to the Boston Bruins for Andrew Raycroft.

At the end of 2005-06 season, the Leafs let Ed Belfour go, which left a massive void in goal that was to be filled in by the incoming Raycroft. With both Rask and Justin Pogge in the system, the Leafs decided to punt on the former rather than the latter.

The most fascinating part is that the Leafs weren't getting Raycroft fresh off his rookie-of-the-year season as he struggled to the tune of 8-19-2 with a 3.72 GAA and a .879 SV% in 2005-06. Nevertheless, then general manager John Ferguson Jr. felt the need to make the move, which ultimately crippled the organization for years to come.

Raycroft ended up lasting 2 seasons, the first in which he allowed a league-high 205 goals in 72 games played, and the second season he played 19 games to Vesa Toskala's 66 before being bought out that summer.

As for Rask, he posted a 308-165-66 record across 544 starts in 15 seasons with the Bruins, where he recorded a career .921 SV% and a 2.28 GAA with 52 shutouts. He was also 57-46 in the playoffs with similar peripherals as he posted a .925 SV% and a 2.22 GAA.

Rask won the Vezina trophy in 2014 after going 36-15-6 with a .930 SV% and a 2.04 GAA with 7 shutouts. For context, that very same season, the Maple Leafs managed only 2 more wins than Rask as they finished the year with a 38-36-8 record.

Rask became one of the best goalies in the modern era and he ended up playing his entire career with the Bruins. Raycroft on the other hand barely lasted 2 seasons, making way for a carousel in goal for years to come.