Round 1
9th Overall - MIkhail Sergachev
Sergachev made the Canadiens out of his first training camp, playing four games before returning to the Windsor Spitfires. That would be the last Habs fans would see of Sergachev, as the Canadiens traded him to the Tampa Bay Lightning for Jonathan Drouin in the 2017 NHL Draft.
The rest is history for the Canadiens. Drouin had a less-than-stellar career in the blue, blanc, et rouge, and Sergachev is one of the main pieces on a two-time Stanley Cup Champion in Tampa Bay. To add insult to injury, the Lightning were the team that defeated the Canadiens in the 2021 Stanley Cup Final. The trade is one of the worst of the Marc Bergevin era.
Round 3
70th Overall - Will Bitten
Bitten signed a three-year, entry-level deal with the Canadiens at the end of the 2017-18 season. He attended training camp with the Habs, but they traded him to the Minnesota Wild for Gustav Olofsson before the season began. Bitten played four games with the St. Louis Blues in 2022-23, the only ones of his career.