The top-5 worst Leafs draft picks of the Shana-Plan era
Although the on-ice success of the Toronto Maple Leafs hasn't been what the team was expecting when Brendan Shanahan took over as team president in 2014, the culture has undeniably shifted in Toronto. Shanahan didn't go all scorched Earth right away. He waited to see how things would pan out and when it became inevitable, Shanny cleaned house and the rebuild that Leaf Nation refers to as the "Shanaplan" was born.
With Shanahan as the team's spearhead, the Leafs have put an emphasis on drafting and developing young players, including but not limited to Auston Matthews, Mitch Marner, and William Nylander - who were all top 10 picks by the Leafs. Some depth pieces, such as Pierre Engvall, were drafted in the later rounds, but for every Pierre Engvall that the Leafs found in the late rounds there are many players that never went on to play for the Leafs.
Some botched drafts early into the rebuild had set the franchise back in the depth department. Some of these picks and the philosophy of drafting like it was 1996 instead of 2016 led to some draft picks that are certainly worthy of being on this list.
*Disclaimer* the players listed as who the Leafs should have picked need to have been selected within 10 spots of the Leafs' actual pick in order to qualify for this list.
Anyways, here are the top 5 worst Leafs draft picks of the Shana-Plan era.
5 - JOSEPH WOLL: #62 OVERALL IN 2016
Joseph Woll may be on the cusp of becoming an NHL goalie and actually has some pretty good numbers in 4 appearances for the Leafs this year. Woll owns a 3-1-0 record with a .911 save percentage and he even picked up his first career shutout on November 21st 2021 against the New York Islanders.
Woll put up solid numbers in the NCAA with Boston College, posting a .916 save percentage across 3 seasons. He also won a gold medal with Team USA at the 2017 World Juniors. Given how Woll has developed so far, he could yet prove to have been an excellent pick. That being said - what may haunt Leafs fans is who was taken 66th overall in that draft.
The reigning Norris Trophy winner, Adam Fox was selected 66th overall by the Calgary Flames. Fox won the Norris Trophy in 2021 and he quickly become one of the best defenceman in hockey. He is the typical modern day defenceman. He's 5'11 but he is very mobile with the puck, players great in transition, and is still an effective player in his own zone. Fox would do wonders for the Leafs blue line.
The only reason that this one doesn't rank higher on the list is because Fox refused to sign with the Flames and he forced his way to the New York Rangers. He may have done the same with the Leafs had they have taken him 62nd overall.
4 - ANDREW NIELSEN: #65 OVERALL IN 2015
Andrew Nielsen is your typical Mark Hunter draft pick - a big 6'4 defenceman who wasn't afraid to throw his weight around. This style of drafting has been a bit of a black mark for the Leafs when Mark Hunter ran their drafts between 2015 and 2017. Unfortunately, Nielsen never made it to the NHL and is currently playing for the Colorado Avalanche's ECHL affiliate.
At #72 overall, the Tampa Bay Lightning took Oshawa Generals captain Anthony Cirelli. Cirelli was coming off of a Memorial Cup run where his Generals knocked off Connor McDavid's Erie Otters in the process. Cirelli is an example of how the Lightning's drafting lead to back-to-back Stanley Cup. Undersized forwards were undervalued in drafts and it lead to a lot of steals for the Lightning, including Cirelli.
3 - J.J. PICCINICH: #103 OVERALL IN 2014
J.J. Piccinich was selected 103rd overall by the Leafs in 2014. The Paramus, New Jersey native showed signs that he could be a good NHL player after two stellar seasons with the London Knights. Unfortunately, Piccinich struggled after turning pro. He played just 10 AHL games and the majority of his pro career in North America was played in the ECHL. Piccinich is having a great season with the Belfast Giants of the EIHL but he isn't the NHL contributor that two players picked shortly after him have become.
Devon Toews was the first NHL regular selected after Piccinich as he was drafted 108th overall by the New York Islanders. The Islanders had to move on from Toews because of the salary cap but Toews has blossomed into one of the best shutdown defenders in the NHL.
Toews plays exceptionally well next to Cale Makar and he was a dark horse candidate to play for Team Canada at the Olympics prior to the NHL pulling out. Toews is the caliber of defenseman that many fans are screaming for the Leafs to trade for at the trade deadline.
The other NHL regular is Viktor Arvidsson, picked 112th overall in 2014. Arvidsson played a key role in Nashville's Stanley Cup Finals run in 2017. While he is certainly small, he is a tenacious player and at just $4.25 million, he would look fantastic in the Leafs top-6 right about now.
2 - DMYTRO TIMASHOV: #125 OVERALL IN 2015
Timashov put up great numbers in the QMJHL and looked like he was well on his way to becoming a late round steal. Timashov made the transition from junior to pro in 2016 and had 3 productive seasons for the Toronto Marlies, including a Calder Cup in 2018. Timashov played 39 games for the Leafs and produced at a decent rate. The issue for Timashov was that he was not skilled enough for top-6 role but not physical enough for the bottom-6. This is what lead him back to Sweden after stints with the Red Wings and Islanders.
Ten picks later at 135th overall, the Minnesota Wild took the steal of the best draft when they got Kirill Kaprizov. Kaprizov stayed in the KHL for 5 years after being drafted but when he arrived to Minnesota in 2021, he lived up to the hype. Kaprizov won the Calder Trophy and has been even better this season and is tied for 8th in league scoring currently. If there's one positive to take out of this for Leafs fans it's that the Bruins traded away this 5th round pick that became the face of the Minnesota Wild.
1 - YEGOR KORSHKOV: #31 OVERALL IN 2016
We all knew this was coming. In 2016 the Leafs chose to draft an overaged 6'3 Russian forward in Yegor Korshkov with the 31st overall pick in 2016. The Leafs passed on one of the best players in the OHL in order take the 65th ranked prospect. Korshkov was eventually traded to the Carolina Hurricanes in the Alex Galchenyuk trade. He has played just 1 NHL game in which he scored for the Leafs, but at this point, Korshkov is looking like a career KHL player.
The Leafs passed on two 2022 Central Division All-Stars when they reached on Korshkov. The one that is often talked about is Alex DeBrincat, who was drafted 39th overall. While small, he would likely go in the top-10 if the draft was redone today.
DeBrincat had two 50-goal seasons and a 65-goal season in the OHL. In the NHL, DeBrincat has 145 goals and 120 assists in 345 career games. DeBrincat sits 4th in goals this season, ahead of even Auston Matthews.
The Leafs also passed on Jordan Kyrou, who was picked 35th overall by the St. Louis Blues. A Toronto native, Kyrou is having a breakout season for the Blues. In 38 games this season, Kyrou has 41 points. He has been a great contributor for the Blues and would have undoubtedly looked good in a Maple Leafs jersey.
Both options blow Korshkov's production out of the water. Had Mark Hunter picked DeBrincat or Kyrou over Korshkov, it could be the difference between the Leafs winning and losing a playoff round with their current core.
This list is depressing. If there's one thing we can take comfort in, it's knowing that current Leafs GM Kyle Dubas appears to have hit on several picks beyond the first round during his tenure and has done a great job restocking the prospect cupboards after Hunter and Lamoriello had left them pretty bare.
