Sometimes I google player names just to see what happens. Other times I pick a date and look to see if the Leafs made a trade then. Last night I thought I’d check out preseason trades the Leafs have made, and found something odd.

The 1999-2000 NHL season began on October 1st, 1999 and between games one and nine the Maple Leafs made four trades. Four trades in four weeks, after they had spent three weeks building the team in training camp.

The 1999-2000 roster didn’t really need a lot of tinkering to start with. Pat Quinn was coach, and the newly named GM and had a pretty good roster to start with: Mats Sundin was coming into his third season as captain, Bryan Berard was the next big thing looking to make a name for himself, Curtis Joseph established his role as the starter in net, Tie Domi was punching people in the neck, and a young Tomas Kaberle was dreaming of playing in the NHL but never actually shooting the goddamn puck.

The team itself was coming off a Conference Final loss to the Buffalo Sabres, coming just five wins short of their fourteenth Stanley Cup. When the Leafs were packing to head to Montreal for opening night, Quinn looked at his roster sheet and decided he needed to tweak his defense.

On October 1st, 1999 the Toronto Maple Leafs traded winger Frederik Modin to the Tampa Bay Lightning in exchange for defender Cory Cross (and a seventh round pick that become Ivan Kolozvary. Who? Exactly.) Modin was a three year NHL veteran, who was adding about 12 goals a year for the Leafs at that time. Modin would play 445 games for the Lightning, with his best season coming in 2003-04 where he scored 29 goals and 28 assists in 82 games - the only season he played all 82 games. Oh, and he won the Stanley Cup that season. Cory Cross lasted three seasons with the Leafs, added 35 points, then left to sign with the New York Rangers in the 2003 off-season.

One week later, Quinn was in this office looking at his players and thought “Man, this Sylvain Cote guy’s name is a pain to spell on roster sheets. He needs to go.” Off he went, after three games played that season, to the Chicago Blackhawks for a 2001 2nd round pick (Karel Pilar), and a 2001 third round pick (Nicolas Corbeil). Was this a good deal? Well, Cote was on the downturn of his career - he’d be flipped by the Blackhawks to the Stars, then play two more seasons for the Capitals before getting one NHL game in 02-03 and retiring. For the Leafs, Pilar would split three season between Toronto and St. John’s before saying “bugger this” and heading back to the Czech Republic. Nicolas Corbeil never saw NHL action and ended up a career player in the Quebec goon league.

Finally, October 20th was the day Pat got it all out of his system. First, he traded long time NHL vet Derek King to the St. Louis Blues for Tyler Harlton. King was first round pick in 1985 for the New York Islanders, coming in just after the dynasty ended. He had only played three games for the Leafs, and would only play 19 for the Blues in what became his final NHL season. Harlton was in the AHL at the time of the trade, and played 136 games for St. John’s before ending his career 17 games into the 01-02 season.

The last move is a bit of an odd one. Dmitri Khristich had played two seasons for the Boston Bruins, scoring 71 points in the 98-99 season. An arbitrator awarded him a four year deal worth $10,000,000 but the Bruins refused to sign him to that contract. The Leafs were interested in him so they signed him as a free agent. The twist is the Bruins still owned his rights, and were due compensation for losing him. The NHL never disappoints with weird rules. So, the Leafs sent the Bruins a second round pick in the 2000 draft. Worth it? No.

Khristich lasted a quarter of the way through the 00-01 season before being traded to the Washington Capitals for the pick that became Brendan Bell and left for Russia in 2002. The Bruins drafted Ivan Huml who would bounce between Boston and Providence for his ELC years, then go on to play in the Czech and Finnish leagues; he’s currently playing for HC Risuty in the Czech 3rd division.

That is the story of the busiest October in Leafs history. I originally set out to talk about Leafs preseason trades, but it was just a 5,000 word piece yelling at Brian Burke for not offer sheeting Phil Kessel, rather than trade for him (WE COULD HAVE KEPT THE DOUGIE HAMILTON PICK!).