In the most recent expansion draft in 2000, Toronto had two players - Finnish defenseman Tommi Rajamaki and centre Kevyn Adams - taken by the Columbus Blue Jackets; a year earlier, the Atlanta Thrashers plucked defenceman Yannick Tremblay from the Buds; in the 1998 draft, the Nashville Predators took blueliner Rob Zettler off the Buds' roster; in the 1993 expansion process, the Leafs had goalie Darren Puppa selected by the Florida Panthers and winger Joe Sacco taken by the Mighty Ducks of Anaheim; and in the 1992 draft, Toronto lost forwards Brian Bradley and Keith Osborne to the Tampa Bay Lightning. 

In the 1991 expansion draft - a more convoluted process that saw the San Jose Sharks select 14 skaters and two goalies from the Minnesota North Stars, followed by a draft that allowed the Sharks and North Stars to each select 10 players from the remaining 20 teams in the league - the Leafs had veteran D-man and former captain Rob Ramage taken by Minnesota. 

Prior to the NHL's last great burst of expansion in the past 26 years, the league has held five additional expansion drafts dating back to 1967. In 1979, the league welcomed four new clubs - the Edmonton Oilers, Winnipeg Jets, Quebec Nordiques and Hartford Whalers, all of which had come from the defunct World Hockey Association - and Toronto had five players (or at least, their playing rights) taken: blueliner (and future Leafs assistant coach) Rick Ley and D-man Kevin Kemp were picked by Hartford, and forward Jordy Douglas, who was drafted by Toronto 81st overall in 1978 yet never played for the Leafs, remained with the Whalers franchise; and winger Lorne Stamler and goalie Pierre Hamel went from Toronto to the Jets.

Five years sooner, the Leafs lost three players in the expansion draft that stocked the Washington Capitals and Kansas City Scouts: goaltender Ron Low, winger Denis Dupere and blueliner Joe Lundrigan all were claimed by the Caps. In the 1972 expansion draft, the Atlanta Flames selected Billy MacMillan, and the New York Islanders took winger Brian 'Spinner' Spencer and centre Tom Miller off Toronto's roster. In 1970, the Buffalo Sabres and Vancouver Canucks joined the league, and the Buds lost four players in total: the Sabres chose D-man Chris Evans, while the Canucks took blueliner Ron Ward, centre Danny Johnson, and defenceman (and future Leafs legendary coach) Pat Quinn. 

And in the very first NHL expansion draft in 1967, six teams joined the Original Six and, like the other five existing teams, the Leafs lost a whopping 20 players to the new clubs: goalie Terry Sawchuk was the very first player selected, moving from Toronto to the L.A. Kings; netminder Gary Smith also went from the Leafs to California, only he went to the Golden Seals franchise; Buds defencemen Bob Baun, Kent Douglas and Aut Erickson also joined the Seals, as did Toronto forwards Terry Clancy and Mike Laughton. Leafs forwards Bill Flett, Lowell MacDonald, Mike Corrigan, and Eddie Joyal joined Sawchuk with the Kings. Forwards Brit Selby and Don Blackburn became ex-Leafs when the Philadelphia Flyers selected them, and winger Larry Jeffrey went from Toronto to the Pittsburgh Penguins in that same draft. The Minnesota North Stars didn't select a single Leaf, but the St. Louis Blues selected six players off Toronto's roster: defenceman (and future Hockey Hall of Famer) Al Arbour, blueliners Darryl Edestrand and Fred Hucul, and wingers Larry Keenan, John Brenneman and Gary Veneruzzo.

With that much history behind them, then, the Leafs are set for Wednesday's draft. As with all expansion drafts, the rules are different this time. Each of the 30 current franchises had two options of groups of players they wished to protect from being claimed by Las Vegas: they could protect seven forwards, three defencemen and one goalie, or eight skaters in any combination of forwards/defencemen and one netminder. Any player who had a "no movement" clause in his contract (and who declined to waive it at the team's request) had to be protected by their team, and all first-and-second-year professional players as well as unsigned draft choices were automatically exempt from being selected by the Golden Knights.

Las Vegas has guidelines of their own they must adhere to, including choosing only one player from each of the 30 teams. By the end of the expansion draft, Golden Knights GM George McPhee must have selected 14 forwards, nine D-men and three goalies; in addition, 20 of the players he picks must be under contract for the 2017-18 season, and the roster must have an aggregate expansion draft value between 60-100% of the 2016-17's upper limit for the salary cap. Finally, the Golden Knights are not permitted to buy out the contracts of any player selected Wednesday until the summer of 2018.

With that said, there's an expectation McPhee and his management team will do an incredible amount of wheeling and dealing when the expansion draft process is all said and done. Will the Maple Leafs be participants in any of those deals? Only time will tell