Quite a few choices for you today. None played 700, or a thousand games or had decades of experience with the Leafs, but they made an impact while they were here.

Bill Derlago (1979-86)
Stats 378GP - 158G - 176A - 334Pts - 179PM

A first round pick for the Canucks, he would play only 63 games for them before being traded to the Maple Leafs with Rick Vaive for Jerry Butler and Tiger Williams. He would play six seasons for the Maple Leafs, and played centre for Rick Vaive most of their time on the team together. Derlago would be traded to the Boston Bruins early in the 85-86 season for Tom Fergus.

Joffrey Lupul 2011-Present
Stats: 280GP - 88G - 94A - 182Pts - 161PM

Joffrey Lupul came to the Maple Leafs in a trade NOT involving Chris Pronger. He was traded by the Ducks to Toronto along with Jake Gardiner in exchange for Francois Beauchemin. Lupul wasn’t getting along with Ducks coach Randy Carlyle, and needed a change of scenery.....

Despite being reunited with Carlyle, Lupul was a mainstay on the Maple Leafs wings despite never playing more than 69 games in a season. Halfway through the 2015-16 season he was placed in injured reserve, and he hasn’t been seen with the Leafs since then. Controversially on LTIR for the second season, his contract expires at the end of this season.

Kent Douglas (1962-67)
Stats: 283GP - 20G - 65A - 85Pts - 408PM
Awards: Stanley Cup -  1963, 64 / Calder Trophy - 1963

Joining the Maple Leafs after four seasons with the Springfield Indians, Douglas would win the Calder trophy and two Stanley Cups before being sent down to the Tulsa Oilers in the 66-67 season, missing out on the 1967 cup win. He would be picked up by the Oakland Seal in the 1967 expansion draft.

Tom Fergus (1985-91)
Stats: 357GP - 118G - 179A - 297Pts - 324PM

Fergus came to Toronto in exchange for another #19, Bill Derlago. He was one of Toronto’s top players in the 85-86 season, but before the next year began he came down with a viral infection that limited him to 57 games. After three seasons as a high scoring centre, but not a defensive one, Fergus had off-season groin surgery that made him miss almost all of the 90-91 season. He would be traded to the Canucks for cash mid-way through the 91-92 season.

Paul Henderson (1967-74)
Stats: 408GP -162G - 156A - 318Pts - 166PM

Paul Henderson is most famous for scoring the winning goal in the 1972 Summit Series. He did so while a member of the Maple Leafs, arriving from the Red Wings as part of a seven player deal, including Frank Mahovlich going the other way. After seven seasons with the Maple Leafs, including some seasons ruined by injuries and struggling with his fame after the Summit Series. He didn’t have a great relationship with Harrold Ballard (who did?) and he left the NHL to play for the Toronto Toros of the WHA. He retired after the 79-80 season spent with the Atlanta Flames. He was inducted into the IIHF hall of fame in 2013.

Joe Klukay (1946-52 / 55-56)
Stats: 360GP - 68G - 86A - 154Pts - 24PM
Awards: Stanley Cup - 1946, 47, 49, 51

Klukay won four Stanley Cups with the Maple Leafs in the late 40’s and early 50’s. Before the 52-53 season he would be traded to the Boston Bruins for cash, and would return two years later in exchange for Leo Boivin. After the 55-56 season, he would play Senior a in Windsor, and win the Allan Cup.

Fredrik Modin (1996-99)
Stats: 217GP -38G - 38A - 76Pts - 36PM

Modin joined the Maple Leafs as a free agent from Sweden and played three full seasons with the Leafs. A fairly productive winger, Modin was traded to the Lightning at the start of the 99-00 season, for Cory Cross and a 7th round pick.

Other 19’s

Hugh Bolton (1953-55)
Stats: 78GP - 2G - 19A - 21Pts - 65PM

Bolton spent five years going up and down trying to secure a spot on the Maple Leafs. He did so in the 54-55 season, and would stick for two more after that.

Bruce Boudreau (1976-80)
Stats: 83GP - 17G - 26A - 43Pts - 20PM

The Haagen-Daas loving coach wore four numbers with the Maple Leafs, but none longer than the four seasons he spent in #19, but all were splitting time with the AHL. Most of his career would be spent in the minors before he began coaching. He’s currently head coach of the Minnesota Wild.

Barry Cullen (1955-59)
Stats: 164GP - 28G - 43A - 71Pts - 88PM

Brother of former Maple Leaf Brian Cullen, Barry had two split seasons and two full seasons with the Maple Leafs in the 50’s. He would also play for the Red Wings, but spend most of his career in the minors.

John Cullen (1992-94)
Stats: 100GP - 26G - 45A - 71Pts - 120PM

Barry’s grandson John also got in 100 Leafs games, Cullen came to the Leafs for a 2nd round pick from the Hartford Whalers. After the 93-94 season Cullen would play for the Penguins and Lightning before retiring.

Jeff Farkas (2000-01)
Stats: 2GP - 0G - 0A - 0Pts - 0PM

His first regular season call up with the Maple Leafs lasted only two games before being sent back to the minors.

Bill Flett (1974-75)
Stats: 77GP - 15G - 25A - 40Pts - 38PM

Coming to the Leafs in an off-season trade from the Flyers for Dave Fortier and Randy Osburn, Flett played on season in Toronto before leaving for the Atlanta Flames.

Greg Hubick (1975-76)
Stats: 72GP - 6G - 8A - 14Pts - 10PM

Acquired from the Montreal Canadiens for Doug Jarvis, the defensive defender played one season with the Maple Leafs. He spent the rest of his career in the minors, aside from a brief call up by the Canucks.

Gerry James (1954-56)
Stats: 47GP - 3G - 3A - 6Pts - 50PM

#19 was his first out of junior hockey, he would wear two more with the Leafs in later seasons.

Kenny Jonsson (1994-96)
Stats: 89GP - 6G - 29A - 35Pts - 38PM

A first round pick by the Leafs in 1993, Jonsson would be traded to the New York Islanders along with Sean Haggerty and Darby Hendrickson and a 1st (Roberto Luongo) in exchange for Wendel Clark, Mathieu Schneider and future coach D.J. Smith. Jonsson would play eight seasons on the Islanders blue line before returning to Sweden to captain Rogle for four seasons.

Dmitri Khristich (1999-2000)
Stats: 63GP - 12G - 18A - 30Pts - 24PM

The former Capitals draft pick signed with the Leafs after leaving the Bruins as a free agent. The following season he would be traded to the Capitals in exchange for a 3rd round pick. He is currently the head coach of the Edinburgh Capitals of the EIHL.

Dominic Moore (2008-09)
Stats: 101GP -16G - 39A - 54Pts - 83PM

In Moore’s first stint with the Maple Leafs, he came to Toronto after the Leafs claimed him off waivers from the Wild in January 2008. At the 2009 trade deadline Moore would be sent to the Buffalo Sabres for a second round pick when neither side could agree on a contract extension.

Eric Nesterenko (1952-53)
Stats: 35GP -10G - 6A - 16Pts - 27PM

Joining the Leafs in the 52-53 season out of junior hockey, Nesterenko racked up 16 points. He would switch to #16 after making the Leafs full time.

Mikael Renberg (2001-04)
Stats: 35GP -10G - 6A - 16Pts - 27PM

In the 2001 off-season the Maple Leafs acquired Renberg from the Coyotes for Sergei Berezin.When the 04-05 season was cancelled, Renberg went back to Sweden and finished his career after five seasons in the SHL.

Alexander Suglobov (2006)
Stats: 2GP -0G - 0A - 0Pts - 0PM

Acquired from the Devils for Ken Klee at the 2006 deadline, he would play most of the remainder of the season for the Marlies, and switch to #9 the following season.

Rick Vaive (1980)
Stats: 22GP - 9G - 7A - 16Pts - 77PM

Vaive wore #19 in the half season he spent here after being traded by Vancouver. He would switch to #22 the next season.

Johnny Wilson (1959-61)
Stats: 73GP - 15G - 17A - 32Pts - 8PM

Brought over in the 1959 off-season with Frank Roggeveen for Barry Cullen from the Blackhawks, Wilson He would play a season and a half with the Leafs before being traded to the Rangers for Eddie Shack.

Who was the best #19 for the Maple Leafs?

Bill Derlago113
Joffrey Lupul93
Kent Douglas4
Tom Fergus27
Paul Henderson237
Joe Klukay9
Fredrik Modin 21
Hugh Bolton0
Bruce Boudreau8
Barry Cullen1
John Cullen2
Jeff Farkas 0
Bill Flett 1
Greg Hubick0
Gerry James 0
Kenny Jonsson 14
Dmitri Khristich 3
Dominic Moore8
Eric Nesterenko0
Mikael Renberg 11
Alexander Suglobov 4
Rick Vaive85
Johnny Wilson1