4 players that the Toronto Maple Leafs gave up on too soon this century

Over the years, the Toronto Maple Leafs have meticulously drafted many promising prospects with sincere hopes that, some day, they could actually help the team in one way or another.

For some of those prospects, like Morgan Rielly, Auston Matthews, Mitch Marner and William Nylander to name a few, they have evolved and became an integral part of the Toronto Maple Leafs roster for many years. Whereas for many others that were less fortunate, they did not end up lasting long enough to stay within the organization to provide the potential impact that was expected of them.

However, there have been a select few of those castoffs that have managed to find some level of success after leaving the Maple Leafs organization. In fact, some had even gone on to make significant contributions with their new teams in helping them become a winner. As a result, had the Leafs held onto them a little longer, things could have been a lot more different in their perennial quest for the Stanley Cup.

Here, we will take a look at four players that the Maple Leafs actually gave up on just a little too soon within this part of the century. And just to the luck of the Leafs, these players ended up being key pieces on their new teams, with some even leading them to the elusive Stanley Cup.

With the surprising trades by the Leafs of both of their young defensemen in Rasmus Sandin and Timothy Liljegren in recent years, hopefully they don’t end up on this distinguished list in the not-so-distant future as well. Otherwise, the Maple Leafs could be regretting the lost as much as some of these precious talents that they once had a firm grasp of.

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.

Alexander Steen

Similar to Boyes, Alexander Steen was also taken in the first round, 24th overall by the Leafs, but this time from the 2002 NHL Entry Draft. But unlike Boyes, Steen actually got his chance to suit up for the Maple Leafs starting from the 2005-06 season. Despite averaging double-digit in goals and close to 40 points per season in his first three years with Toronto, Steen appeared to struggle in reaching the next level in his game to provide more of an offensive impact for the Leafs. 

As a result, during the 2008-09 season, Steen was ultimately dealt to the St. Louis Blues along with defenceman Carlo Colaiacovo for right winger Lee Stempniak.

Stempniak had once put up 27 goals during the 2006-07 NHL season, so the Leafs were hoping that his better scoring touch could make a difference for the club. Unfortunately, those 27 goals would turn out to be the most he would have in one season for the rest of his NHL career as he put up just 11 and 14 goals for the Leafs in his two years with the team.

As for Steen, he would become an important piece of the Blues’ top-six for over the next 12 years, all the way until his eventual retirement.

In 765 total games, he registered 195 goals, 301 assists for 496 points, including four seasons of 20+ goals and five seasons of 30+ assists. More importantly, he played a role in helping the Blues to their first ever Stanley Cup win in 2018-19.

Steen would finish off his career by reaching his NHL milestone 1000th game during his final season in the league as well. With his loyalty and solid play over many seasons with St. Louis, he could have done exactly the same with Toronto and perhaps could have even been a factor in helping them reach the playoffs.

Tuukka Rask

Finally, we have perhaps the biggest mistake that the Leafs made in perhaps the history of the franchise.

With Toronto moving on from Ed Belfour following the 2005-06 campaign, the Leafs needed a proven starting goalie ahead of the 2006-07 season. In their search for a No. 1 goaltender, Boston Bruins Andrew Raycroft caught their eye as he was a former Calder Trophy winner back during the 2003-04 season.

Having fallen out of favour in Boston, the Leafs jumped on what they though was a fortuitous opportunity to work out a trade for Raycroft with the Bruins. With the choice of including either goalie Justin Pogge or first round pick Tuukka Rask as part of the return, Toronto decided on Rask, given Pogge was coming off a spectacular 38-win season with the WHL Calgary Hitmen and a gold medal win from the World Juniors Hockey Championship.

That fateful decision has ended up haunting the Leafs for almost to the end of eternity ever since. For Raycroft, he would post two underwhelming seasons with Toronto despite putting up 39 wins in total. For Pogge, it was even worse as he would appear in just seven games for the Leafs for his entire NHL career.

As for Rask, he would eventually become a mainstay in the Bruins net for over a decade, posting a stellar record of 308-165-66 with 52 shutouts, along with a lifetime 2.28 GAA and .921 save percentage. On top of that, he was part of the Stanley Cup winning team in 2011, he had captured the Vezina Trophy and was named to the NHL First All-Star team in 2014, along with the William Jennings Trophy and NHL second All-Star team in 2020. (All stats from hockey-reference.com)

More importantly, Rask would have been the solution to the Leafs net for pretty much the bulk of this part of the century, instead of circling through numerous failed options over the years. And if it wasn’t already bad enough that the Leafs made the wrong decision back then in who they gave up, it was learned later that the Bruins actually intended to release Raycroft prior to the trade.

So the Leafs could have even had Raycroft without giving up any assets at all. But instead, they gave away one of the best goaltenders to have played during the past two decades in the NHL. Painfully, without a doubt, Rask would have been a huge difference maker for the club in their Stanley Cup hopes all these years.