Brad Boyes
The Maple Leafs had high hopes for Mississauga native Brad Boyes after they selected him in the first round, 24th overall from the 2000 NHL Entry Draft. After all, as a prolific 30+ goal scorer in juniors, Boyes was named OHL’s most outstanding player in consecutive seasons in 2000-01 and 2001-02.
In addition, he proved that he could also be a winner when became a beast in the OHL playoffs for the Erie Otters during the 2001-02 season. Boyes ended up posting 22 goals and 19 assists for 41 points in just 21 games played to help the Otters win the OHL championship.
Boyes appeared to be well on his way to making the Leafs everyday lineup soon when he put together a strong first season with their AHL-affiliate St. John’s in 2002-03, recording 23 goals and 28 assists for 51 points in 65 games played.
However, with the Leafs in need of an offensive push for the playoffs, Boyes became part of the package sent to the San Jose Sharks in the trade for star power forward Owen Nolan. Unfortunately, Nolan was already on the decline at that stage of his career as he ended up compiling just 26 goals and 60 points in 79 games played over two seasons with the Leafs. Toronto would be ousted in the first round in his first year and failed to make the playoffs entirely in his second season.
As for Boyes, he would eventually rise to prominence in his rookie season with the Boston Bruins in 2005-06 where he put up 26 goals and 43 assists for 69 points over 82 games played. He would end up tied for fifth in the Calder Trophy voting that year. From there, Boyes would move on to the St. Louis Blues in 2006-07 in a trade where he would have his best years of his career, including two consecutive 33+ goal seasons between 2007-08 and 2008-09.
He would eventually come full circle back to the Leafs in 2015-16, but by then, it was already the twilight of his NHL career. Had Boyes remained with Toronto during his prime years, perhaps the Leafs playoff drought wouldn’t have lasted more than the eight years between 2005 to 2012. More importantly, it would have given Mats Sundin an actual elite right winger to play with and not waste his final few seasons with the Leafs.