January 31st was a busy trading day in Toronto Maple Leafs history. The majority of the trades have come in the last 20 years, but one reaches all the way back to the time when a team called the Ottawa Senators was good. With six trades on this date, we have some history to go through.

January 31st, 1930

To Toronto:
Frank Nighbor

To Ottawa:
Danny Cox

The first one on this list brought a great NHL player to the Maple Leafs at the end of his career. Frank Nighbor was a three-time Stanley Cup Champion with Ottawa (1921, 23, 27), two time Lady Byng trophy winner (1925, 26), and he was the first player to ever win the Hart trophy, in 1924. This was his return to Toronto, where he played one season with the National Hockey Association’s Toronto Blueshirts. scoring 25 goals in 19 games.  This time around Nighbor scored just two goals in 22 games for the Leafs, and retired after the team failed to make the playoffs.

Nighbor would be named to the Hockey Hall of Fame in 1947.

The Ottawa Senators were - shockingly - in financial trouble at the time of the trade, and were selling off any and all highly paid players. Danny Cox was a player they could afford and he would play 69 games for the Senators before being claimed by the Detroit Falcons in the 1931 dispersal draft ahead of the 31-32 season. The money was probably the biggest part of the trade for Ottawa.

January 31st, 1961

To Toronto:
Don Simmons

To Boston:
Ed Chadwick

Don Simmons played only 58 games over three seasons with the Maple Leafs, but he was on the team when it counted as he was part fo the 1962, 63, and 64 Stanley Cup winning Maple Leafs teams.

Ed Chadwick was a goalie who joined the Maple Leafs in 1956, and made the big club for three straight seasons from 1956-57 to the 1958-59 season, but he would be sent down to the AHL early in the 59-60 campaign, where he remained even after he was traded to the Bruins.

January 31st, 1971

To Toronto:
Bernie Parent
1971 2nd round pick

To Philadelphia
Bruce Gamble
Mike Walton
1971 1st round pick

The Maple Leafs thought they had a new starter to take them into success in the 70’s, so much that they traded their current starter Bruce Gamble, as well as a first round pick that turned into Pierre Plante, who would play 599 NHL games with 297 points (125G, 172A) - Mike Walton would be flipped to the Bruins the same day.

Bernie Parent played with his idol Jacques Plante for one and a half seasons before leaving the Maple Leafs for the World Hockey Association, as many Maple Leafs did when Harold Ballard refused to match salaries with the rebel league. Parent played one season with the Philadelphia Blazers before returning to the NHL, and the Philadelphia Flyers where Parent would win two Stanley Cups and and two Conn Smythe Trophies.

With the second round pick the Maple Leafs would select Dave Fortier, who would only play 23 games for the Maple Leafs before being traded to the Flyers in 1974.

January 31st, 1997

To Toronto:
Craig Wolanin

To Tampa Bay:
1998 3rd round pick

The 1996-97 season for the Maple Leafs came in the middle of Steve Stavros’ gutting of the team, but this trade was buying a player, not selling. Wolanin was a travelling player, having played for the New Jersey Devils, Quebec Nordiques/Colorado Avalanche, and Tampa Bay Lightning before joining Toronto. His years in Tampa/Toronto were riddled with injuries including a knee injury that ended his 1997-98 season after only ten games. His total Maple Leafs career: 33 games, four assists.

The Lightning would select Alex Henry 67th overall in the 1998 draft with the pick from the Leafs. He would never catch on with the Lightning, but would make his NHL debut in the 02/03 season with the Edmonton Oilers. He would spend most of his career in the AHL, but also made NHL appearances with the Washington Capitals, Minnesota Wild, and Montreal Canadiens. He is currently a development coach with the Arizona Coyotes.

January 31st, 2014

To Toronto:
Teemu Hartikainen
Cam Abney

To Edmonton:
Mark Fraser

We all know Mark Fraser, a favourite of Dave Nonis and the guy who took a puck to the head in the 2013 playoffs. He joined the Leafs at the 2012 trade deadline from the Ducks, and played a total of 68 NHL games with Toronto before being traded to Edmonton. He’s currently playing for HKM Zvolen in Slovakia.

The players we got back didn’t make the NHL. Teemu Hartikainen was an Oilers 2008 6th round pick who had left North America to play in the KHL with Salavat Yulaev Ufa in the 2013 off-season, where he’s been ever since.

Cam Abney was a career ECHLer that Oilers drafted in the 3rd round of the 2009 draft. While with the Leafs he played 13 games with the Orlando Solar Bears.

January 31st, 2010

To Toronto:
Jean-Sebastian Giguere

To Anaheim:
Jason Blake
Vesa Toskala

The first trade on this day in 2010 brought a new starting goalie to the Maple Leafs, who was a Conn Smythe winner and Stanley Cup winner - but in different seasons. After years of Vesa Toskala and Andrew Raycroft Maple Leafs fans thought they were getting the goalie to take them over the top and end the playoff drought that plagued the Leafs since the lost season. He wasn’t a savior, but he was an improvement. However, this trade was just a taste of what’s to come.

To Toronto:
Dion Phanuef
Keith Aulie
Fredrik Sjostrom

To Calgary:
Niklas Hagman
Jamal Mayers
Matt Stajan
Ian White

The biggest deal was saved for last. Nine years ago on this day the Maple Leafs made one of their biggest moves of the cap era when they brought in their first captain after Mats Sundin, and most controversial defender since Larry Murphy, Dion Phaneuf.

We all know enough about Phaneuf, captained the team for six years, traded to the Senators  in a move no one saw coming, and then traded to Ottawa, who then traded himt o Los Angeles with 50% salary retained. So what happened to the rest of the players?

For the Leafs, Fredrik Sjostrom played with the Maple Leafs until 2012, and he then returned to Sweden for two seasons before retiring. He is now in his third season as General Manager for the SHL’s Frolunda HC.

Keith Aulie was looked at as a perfect defense prospect for the Burke/Carlyle team. Big, bruising, and, uh, big. He would bobble between the Leafs and Marlies before being traded to the Tampa Bay Lightning. He mostly played in the AHL, and is currently playing for EHC Munchen of the German league, along with Matt Stajan, who went the opposite way in this trade.

On Calgary’s side, they got Matt Stajan who stayed in Calgary for nine seasons. He played 558 games in Calgary, scoring 59 goals, 131 assists for 190 points. He’s now playing in Germany as noted above, and calls in once every few weeks to the TSN 1050 morning show.

Jamal Mayers was an alternate captain for the Maple Leafs in the 08-09 season. Fun fact right there. He played out that half season in Calgary, then moved on to the San Jose Sharks for one year, and then two seasons with the Chicago Blackhawks, where he would be on the team for their 2013 Stanley Cup win. He would retire after that season, and works in community relations with the Blackhawks and as an on-air personality with NBC Sports Chicago.

Niklas Hagman played with the Flames until early in the 2014-15 season, when he was claimed off waivers by the Anaheim Ducks where he played his final NHL season. After that he would play in the KHL and Liiga (Finland) until retiring after the 2016-17 season.

Ian White was one of the more popular players given up in the trade, and many saw him as a future captain of the team at that time. During the 2011-12 season he would be traded from Calgary to the San Jose Sharks, and then from the Sharks to the Carolina Hurricanes. After that season he played two years with the Red Wings, 10 games in the KHL, and finally one season in the AHL before retiring. He most recently made the news in 2015 after being charged with various firearms offences.

January 31st was quite the busy day for the Maple Leafs trade wise. Will we see anything happen later today?