If you haven't guessed I'm talking about Jared McCann. Now McCann wasn't a Leaf for long and never got into a single game for the Leafs, but he's definitely the one that got away.
The Leaf acquired McCann from the Penguins for a prospect and a pick ahead of the Seattle Kraken expansion draft. Many Leafs' fans were overjoyed as this young controllable left winger was exactly what the Leafs needed. But that joy turned to anger, frustration and confusion rather quickly when Kyle Dubas left him unprotected.
McCann is currently scoring at a 56-point pace, but more impressively he's on pace for 36 goals. McCann is a restricted free agent and would have still remained under team control. McCann's 2.9 million dollar cap hit would have been interchangeable for Nick Ritchie's deal which currently sits in the press box.
McCann has continued to build on his strong season last year in Pittsburgh. With his ability to play center, kill penalties and play on the powerplay it's hard to understand why the Leafs left him unprotected. Especially when the alternative was only losing Justin Holl or Travis Dermott.
In hindsight trying to play 3D chess ultimately cost the Leafs especially when you consider Justin Holl has only ever looked like a serviceable NHLer when paired with Jake Muzzin and no one else.
If the Leafs fail to make the second round again this season, this decision to value Holl over McCann will likely be part of Kyle Dubas end of season interview questions.