22nd Overall Pick: Tyler Biggs (TOR)

Projection: A nasty, hard-working scoring power forward who punishes defencemen on the forecheck, loves to battle along the boards and at the net-front, and is willing and eager to drop the gloves. Questionable upside but likely to be a third line difference-maker. Compared to Milan Lucic by THW and Colby Armstrong and Kyle Clifford by TSN.

Outcome: The Leafs traded up for this pick, and were burned for it. Players that fit the projection above are catnip for general managers and coaches, but Biggs wasn’t that. He could physically dominate at lower levels, but his skill and skating were just not close to good enough for the NHL; hell, they weren’t good enough for the AHL, where he scored at a 0.14 points per game pace in 119 games. 22nd overall picks don’t always pan out, but Biggs serves as a cautionary tale that taking a lack of skill to mean a “safe bottom six” projection often leaves you with a guy who just can’t keep up. He was a throw-in in the Phil Kessel trade and never played an NHL game.

25th Overall Pick: Stuart Percy (TOR)

Projection: An all-around two-way puck-moving defenceman with a stabilizing influence. Smart and solid in all elements of the game, but not exceptional in any sense. Likely a #4 or #5. Compared to Paul Martin by TSN, Dan Hamhuis and Dan Girardi by THW.

Outcome: Brian Burke’s second swing-and-a-miss of the first round, Percy mustered only 11 NHL games in the Leafs’ two tanking years. He showed some encouraging flashes as he developed in their system, playing a high-I.Q. puck-moving game, but dealt with concussions and got lost in the shuffle of the Leafs’ glut of young depth defencemen. There are still some fans who believe that Percy could have been a #4 defenceman if he had been given better opportunities and avoided injury.

5th Overall Pick: Morgan Rielly (TOR)

Projection: A dynamic #1 offensive defenceman with elite passing and skating. Weak defensively and not imposing physically. A top unit powerplay contributor. Compared to Kris Letang by TSN.

Outcome: Brian Burke notoriously thought Rielly was the best player in the draft, and while that didn’t turn out to be true he has comfortably out-performed everyone picked above him. Though he never became one of the league’s top defencemen, his offensive acumen has been impressive and at his peak he was one of the top 5-on-5 offensive drivers in the league. He’s paced above 50 points six times, hitting 72 in 2018-19, and the Leafs have gotten more than 21 minutes a night out of him in eleven of his twelve NHL seasons including some in which he was deployed as a true number one. The scouting report looks basically spot-on, since Rielly’s mobility and especially passing turned out to be major strengths and his defensive play was and is a catastrophic weakness; he ranks last among all defencemen in even strength defensive WAR since 2012.