A few years ago, the Maple Leafs made a choice that could be haunting them in the present day. So much talk about their draft strategy in previous years has led to some players being left out due them not immediately making an impact.
Names like Rasmus Sandin and Timothy Liljegren have found greener pastures elsewhere, but Keaton Middleton, a 6'6, 240 pound towering defenseman could have been the key to Toronto's issues had they signed him. Flourishing in Colorado, it's a big case of "What If?" when it comes to the Leafs.
Originally drafted in the 4th round by the Maple Leafs in 2016, Middleton never got a chance with the team as they refused to sign him. Whether it's due to his analytics, or the team just didn't think he would amount to an NHL regular; he was let go and started to get to work.
The younger brother of current NHLer Jacob Middleton, Keaton ended up joining his brother in San Jose before eventually landing in Colorado. Normally a booming physical presence, Middleton has consistently tried to improve his offensive game and has ended up becoming a solid two-way defender.
So far this season he's been able to get into the Avalanche starting lineup, and while he hasn't registered a point as of yet, it's a remarkable story in regards to where he was just a few short years ago.
It's a shame that Toronto didn't end up keeping Middleton around, as he would fit perfectly with the current regime in charge. Craig Berube no doubt could have used a behemoth two-way defenseman, and Brad Treliving could have saved some money if he had Middleton by refusing to sign Jani Hakanpaa.
Hindsight is always 20/20, and there was no telling what Toronto wanted when they drafted Middleton and then subsequently let him go. He could have been at the very least a third-pairing or seventh defenseman for the team and brought a lot of intimidation to the ice.
The Maple Leafs' loss is the Avalanche's game, and with how the team is built now, there is no doubt that the defenseman could have helped the team immensely.
But for now, the Avalanche reap the benefits of a bad Toronto decision, as the blue and white wonder what could have been.