In the 2020 NHL Draft the Toronto Maple Leafs have the chance to draft in the first round for the 52nd time in franchise history; they could also trade away the first-round pick and skip the round entirely as they have done 13 times before.

As of writing, the Maple Leafs have the 15th overall draft pick, acquired from the Pittsburgh Penguins in exchange for Kapseri Kapanen. Historically the Leafs aren’t great at handling the responsibility of drafting in the first round, with only 29 picks playing more than 100 games for the Leafs; 14 played over 300.

Today we’ll count down the draft from 31st to 16th overall and see how the Leafs made out in the late stages of the first round.

#29 - 2018 - Rasmus Sandin, D, Sault Ste. Marie Greyhounds (OHL)
NHL Career: 28GP - 1G - 7A - 8Pts - 10PM
Leafs Career: 28GP - 1G - 7A - 8Pts - 10PM

The Leafs have never drafted 30th or 31st - spots usually reserved for the Stanley Cup Champions - but made their first 29th overall pick two years ago. Looking at his first round-one pick, Leafs GM Kyle Dubas  made a trade with the St. Louis Blues: moving down from the 25th spot. The Blues would take winger Dominik Bokk with the Leafs’ original pick.

With one and a half seasons on the Marlies, and 28 Leafs games last season, it’s looking like the move down to take Sandin was a good one for the rookie GM.

#25 - 2011 - Stuart Percy, D, Mississauga Steelheads (OHL)
NHL Career: 12GP - 0G - 3A - 3Pts - 2PM
Leafs Career: 12GP - 0G - 3A - 3Pts - 2PM

One of the many first-round misses for the Leafs under Brian Burke, Percy would only last as long as his entry level contract before being released as a free agent. He played 12 games for Toronto between the 14/15 and 15/16 seasons. He played only five games for the Belleville Senators last season. According to Elite Prospects, he signed with Vaasan Sport in Liiga for 2020/21.

#24 - Three picks - 1999, 2000, 2002

1999 - Luca Cereda - C - HC Ambri-Piotta (NLA)
NHL Career: Preferred Switzerland
Leafs Career: Some AHL time

The Maple Leafs first draft pick from Switzerland, Cereda wasn’t a big goal scorer but was a big presence on the ice. He missed the 2000-01 season after being diagnosed with a heart condition and had open heart surgery to repair a faulty valve. He would come back in 2001 and played two and a half seasons with the AHL St. John’s Maple Leafs before returning to the NLA in Switzerland. Since retiring in 2007 he has been coaching in the NLA and for the Swiss national team. He has been the head coach for HC Ambrì-Piotta since 2017.

2000 - Brad Boyes - RW - Erie Otters (OHL)
NHL Career: 822GP - 211G - 294A - 505Pts - 251PM
Leafs Career: 60GP - 8G - 16A - 24Pts - 12PM

Before the draft, Boyes was named the OHL and CHL Scholastic Player of the Year and was heading towards winning two OHL MVP awards, an OHL Championship, an OHL Playoff MVP, as well as World Junior silver and bronze medals. All these pre-NHL honours made him great trade bait, which is why the San Jose Sharks wanted him during his AHL rookie season. Boyes would be traded in a package to the Sharks for Owen Nolan as the Leafs were looking to make a cup run, rather than focus on development. Boyes would sign with the Leafs as a free agent in 2015 to finally play for the team that drafted him for his final NHL season.

2002 - Alex Steen - W - Frolunda (SHL)
NHL Career: 1018GP - 245G - 377A - 622Pts - 454PM - ‘19 Stanley Cup
Leafs Career: 253GP - 50G - 76A - 126Pts - 106PM

The son of former NHLer Tomas Steen, Alex was a successful first-round pick who would go on to play over 1,000 NHL games  - the majority for the St. Louis Blues, with whom he would win a Stanley Cup. Steen played 253 games for the Maple Leafs, before being traded early in the 2008-09 season to the Blues. The hallmark trade of Cliff Fletcher’s second tenure as GM.

#23 - 1992 - Grant Marshall - RW - Ottawa 67’s (OHL)
NHL Career: 700GP - 92G - 147A - 239Pts - 793PM - ‘99 & ‘03 Stanley Cup
Leafs Career: RFA Compensation

Marshall would never play a game for the Maple Leafs, despite a successful rookie AHL season with the St. John’s Maple Leafs. Marshall and Peter Zezel would be sent to the Dallas Stars as compensation for the Leafs signing restricted free agent Mike Craig. Marshall would win the Stanley Cup in 1999 with the Stars and again in 2003 with the New Jersey Devils.

#22 - 2011 - Tyler Biggs - RW - US National Team Development Program
NHL Career: Nothing worth trading up for
Leafs Career: Part of the Phil Kessel trade

Tyler Biggs is a name that sends shivers down the spines of Leafs fans, and another first-round blunder from Brian Burke. The Leafs traded up to draft Biggs, who scored 42 points in 75 games that season in the Team USA program, but his highlight to the Leafs GM was his 200+ penalty minutes. The Leafs sent the Anaheim Ducks the 30th overall pick (Rickard Rakell) and the 39th overall pick (John Gibson) for the pick used to select Biggs, who would never play in the NHL and ended his career with the EIHL (Great Britain) Nottingham Panthers.

#21 - Three picks - 1989, 2005, 2013

1989 - Steve Bancroft - D - Belleville Bulls (OHL)
NHL Career: 6GP - 0G - 1A - 1Pt - 2PM
Leafs Career: Traded for Rob Cimetta

Bancroft was one of three first-round picks from the Bulls in 1989. He would never make it past nine AHL games in the Leafs system before being traded to the Boston Bruins for Rob Cimetta. Bancroft was an excellent AHL player, but never got more than six NHL games over 20 seasons.

2005 - Tuukka Rask - G - Ilves Tampere (Liiga)
NHL Career Stats: 536GP - .922sv% - 2.26GAA - 50SO - ‘11 Stanley Cup, ‘14 Vezina, ‘20 Jennings
Leafs Career: Traded for Calder Trophy winner Andrew Raycroft

Moving on.

2013 - Frederik Gauthier - C - Rimouski Oceanic (QMJHL)
NHL Career Stats: 168GP - 13G - 18A - 31Pts - 45PM
Leafs Career: 168GP - 13G - 18A - 31Pts - 45PM

The much maligned first-round pick has spent the past two season with the Maple Leafs after splitting time between the Leafs and Marlies since turning pro in 2015, the same year he would win gold with Team Canada at the World Juniors. Gauthier is currently an unsigned RFA.

#19 - Landon Wilson - RW - Dubuque Fighting Saints (USHL)
NHL Career Stats: 375GP - 53G - 66A - 119Pts - 352PM
Leafs Career: Traded for Mats Sundin

Wilson would bounce between the NHL and AHL for his hockey life, most of his career spent with the Boston Bruins. His most notable career moment for Leafs fans would be his inclusion in the blockbuster draft-day trade with the Quebec Nordiques that brought Mats Sundin to Toronto.

#17 - Two picks: 2001, 2017

2001 - Carlo Colaiacovo - D - Erie Otters (OHL)
NHL Career Stats: 470GP - 34G - 123A - 157Pts - 231PM
Leafs Career: 111GP - 12G - 21A - 33Pts - 57PM

Old ‘SplodeyBones won the OHL Championship with the Erie Otters before joining the Maple Leafs, and becoming a frequent flyer in the trainer’s office. He never played a full season in the NHL, always hitting the St. John’s Maple Leafs /Marlies a few times a year. He looked to be a full time NHLer in 2008/09, which he was - with the St, Louis Blues after being traded with Alex Steen for Lee Stempniak. That’s it. Two first rounders in one trade for Lee Sempniak. Cliff Fletcher still works with the Leafs!

2017 - Timothy Liljegren - D - Rogle (SHL)
NHL Career Stats: 11GP - 0G - 1A - 1Pt - 2PM
Leafs Career: 11GP - 0G - 1A - 1Pt - 2PM

Apparently falling down to 17 because he had mono, Liljegren jumped right from Sweden to the AHL, making the fatal mistake of not reporting to the Niagara IceDogs, who held his OHL rights. Liljegren has since been overshadowed as the Leafs’ top defensive prospect by Rasmus Sandin, who did play in the OHL. Coincidence?

#16 - 1994 - Eric Fichaud - G - Chicoutimi Saguenéens (QMJHL)
NHL Career Stats: 95GP - .897sv% - 3.14GAA - 2SO
Leafs Career: Traded away unceremoniously

Fichaud would be traded to the New York Islanders at the 1995 trade deadline, lasting less than a year as a Leafs prospect. The Leafs would get back Benoit Hogue, as well as a 1995 third-round pick and a 1996 fifth-round pick. Not a bad return for a career backup and minor leaguer.

Those are the Leafs draft picks from late in the first round. We have some players who were steals for falling so late (but didn’t play for the Leafs), a lot of meh, and a few current prospects who represent the Leafs’ future. Hopefully the top half of the class brings us more joy.

Maple Leafs HistoryNHL Draft