The Toronto Maple Leafs of the late 1990’s weren’t a long term planning team. They were a team looking to win a Stanley Cup and were going to flex their financial muscles rather than their scouting skills to do so.

Leading up to the 1999 draft, the 1996 and 97 drafts saw no first round picks available, and only a couple players picked would become NHL mainstays: Shawn Thornton, Tomas Kaberle, Adam Mair. In 1998 the Leafs picked long time Maple Leafs Nik Antropov in the first round, and Alexei Ponikarovsky in the fourth.

Coming into 1999 things were looking good for the Maple Leafs scouts. They had nine picks in nine rounds to select the players who would grow to become the Maple Leafs of the early 2000’s.

Narrator: They didn’t.

In what could possibly be the worst professional sports draft of all time, the Maple Leafs drafted nine players and saw a grand total of three - yes three - NHL games played out of those picks.

Round One

Luca Cereda - C - Ambri-Piotta, Swiss A League
1998-99 stats - 38GP - 6G - 10A - 16Pts

Cereda was named Swiss A League rookie of the year in 1999, playing against men in a pro league at the age of 17. Ahead of the NHL draft he would end up his Swiss teams #1 centre, with two NHL veterans on his win - Paul DiPietro and Oleg Petrov (sounds familiar...). He was described as the smartest player in the draft and had speed to keep ahead of the older players, despite a sizable frame.

So what went wrong? After his post-draft 1999-2000 season he would be diagnosed with a heart murmur and have open heart surgery, missing the entire 2000-01 season. When he was ready to play again he joined the St. John’s Maple Leafs for three seasons on his ELC, but was not re-signed by the team. He would play 4 more seasons in Switzerland before retiring. He moved into coaching in Switzerland in 2008-09 and was the head coach of the NLA’s HC Ambrì-Piotta last season.

20/20 Hindsight pick: Martin Havlat who would be picked two spots later by the Ottawa Senators.

Round Two

Peter Reynolds - D - London Knights, OHL
1998-99 stats - 59GP - 2G - 25A - 27Pts

“Being drafted by the Leafs was just a dream come true” - more foreboding words were never spoken, just ask Brad Boyes.

Reynolds was a promising two way defender on a pitiful London Knights team, and after being drafted would request a trade off the team and move on to the North Bay Centennials. Not a big scorer, he was seen as a future special teams player by the Maple Leafs at the time of the draft. However after two lackluster seasons in North Bay and a two game try out with the St. John’s Maple Leafs, Reynolds was allowed to re-enter the draft, where he would be selected by the Carolina Hurricanes in the ninth round.

He would retire in the 05-06 season after spending the majority of his career in the ECHL.

20/20 Hindsight pick: Niklas Hagman. Picked 10 spots later in round three by the Florida Panthers.

Round Four

Mirko Murovic - LW - Moncton Wildcats, QMJHL
1998-99 stats - 69GP - 21G - 33A - 54Pts

In 1999 Pat Quinn wanted to increase the size and strength of the Maple Leafs prospects, and power forward Mirko Murovic was one of those players he wanted. A quality forward in the Quebec league, Murovic would see his point totals stay just below the PPG mark until his overage season where he would score 59 points in 54 games.

After junior he went straight to the Swiss leagues where he would play for 13 years.

20/20 Hindsight pick: Ryan Malone, picked seven spots later by the Pittsburgh Penguins

Jonathan Zion - D - Ottawa 67’s, OHL
1998-99 stats - 60GP - 8G - 33A - 41Pts

A scoring defender in the OHL, Zion would stay above 40 points after his draft season, reaching a high of 73 points in 59 games with the 67’s as they won the OHL Championship. After the Maple Leafs passed on signing him he would play in the ECHL and CHL in North America and in England, Denmark, Finland, Sweden, and Austria before retiring in 2014.

20/20 Hindsight pick: Derek McKenzie, picked in round five by the Atlanta Thrashers.

Round Five

Vaclav Zavoral - D - Litvinov Jr, Czech Republic
1998-99 stats - 43GP - 2G - 10A - 12Pts

He was this guy, you know? He moved to the Soo Greyhounds of the OHL after being drafted, but the Maple Leafs let his rights expire. He would bounce around the CHL, UHL, and Czech leagues before settling into a five season run in the English league.

He would later donate some funds to help the Greyhounds build a new arena.

20/20 Hindsight pick: Henrik Zetterberg. Let’s pretend the Leafs picked him two rounds ahead of the Red Wings.

Round Six

Jan Sochor - F - HC Slavia Praha, Czech Republic
1998-99 stats - 47GP - 10G - 11A - 21Pts

¯\_(ツ)_/¯

Never left the Czech Republic for North America, played a chunk of his career in Norway.

20/20 Hindsight pick: Martin Erat, picked by Nashville in round seven.

Round Seven

Vladimir Kulikov - G - CSKA Jr, Russia
1998-99 stats - 14GP - 2.81GAA

Stayed in Russia except for one season in 2000-01 in the Central Hockey League. Went home and played Tier 2⁄3 hockey until retiring in 2010. He’s currently the goaltending coach for the Russian World Juniors team.

20/20 Hindsight pick: Radim Vrbata, picked right after Kulikov by the Avalanche. The bottom slice to Zetterbergs top slice of bread for the shit sandwich that was this pick.

Round Eight

Pierre Hedin- D - MODO, SEL
1998-99 stats - 41GP - 5G - 6A - 11Pts

A good passer according to Elite Prospects, Hedin would be the only pick in this draft to play in the NHL. He would leave Sweden and spend the 2003-4 season with the St. John’s Maple Leafs, where he would be called up for three games in Toronto, scoring one assist for his only NHL point. After that year he would go back and play in Sweden until retiring in 2012.

20/20 Hindsight pick: Jeff Finger, picked right after by the Avalanche. I mean, he was going to end up a Leaf anyways right?

Round Nine

Peter Metcalf - D - Maine, NCAA
1998-99 stats - 33GP - 6G - 17A - 23Pts

Not bad numbers for an NCAA defender, but not enough for a contract. After graduating from college, Metcalf would play in the AHL/ECHL until retiring in 2010.

20/20 Hindsight pick: Pass

The 1999 draft was, aside from Zetterberg, Henrik Sedin, Daniel Sedin, and a few others, one of the worst drafts you could try to build a team from and the Maple Leafs doubled down and essentially passed on this year. We didn’t get a Sedin, but we got three games from a Hedin. Close enough, right?

Maple Leafs HistoryNHL Draft