Top 5 Trades on Valentine's Day in NHL History

The NHL Trade Deadline can, ironically, bring out the worst in teams. Due to the proximity of Valentine’s Day to the NHL Trade Deadline every season, the holiday has grown a reputation for causing earth shattering trades to occur.

In 2023, that was not the case, as no trades broke. However, past history tells us that the chances are always high for big trades to happen on Valentine's Day in the years to come.

5 biggest NHL trades that happened on Valentine's Day

#5 Dustin Tokarski to Canadiens (2013)

For the past 13 years, Dustin Tokarski has been a suitable backup goaltender in the NHL. Tokarski’s best run came in the mid-2010s with the Montreal Canadiens. The trade that set that up occurred on Valentine’s Day, 2013. Tokarski was traded from the Lightning to the Canadiens for Cedrick Desjardins. Desjardins appeared in six total games for the Lightning over the next four years. Safe to say, the Canadiens got the better end of the stick.

#4 Tom Reid to Minnesota North Stars (1969)

Tom Reid is currently a radio color analyst for the Minnesota Wild. In the late 1960s and early 1970s, Tom Reid played a key part in some of the worst Minnesota North Stars teams in the early days of their expansion. Reid later became a local Minnesota legend, and this trade is the reason why. Reid was developed by the Blackhawks organization and made his debut in 1968. After a year and a half, Reid was quickly dealt to the North Stars, their conference rivals. The package was Reid, Bill Orban and Doug Shelton for Andre Boudrais and Mike McMahon Jr. Both McMahon and Boudrais played the worst years of their career in only one season for the Blackhawks before both being shipped out at the end of the season.

#3 Grant Fuhr to Kings (1995)

Talk about a blockbuster! Two NHL All-Star goalies in Grant Fuhr and Robb Stauber were swapped in 1995 when the Kings made a deal with the Sabres. Phillippe Boucher, Denis Tsygurov, and Grant Fuhr went to the Kings for Stauber, Alexei Zhitnik, Charlie Huddy and a fifth-round pick. The Kings got barely anything out of Tsygurov and Fuhr, but Boucher played eight years in LA in the prime of his career. Buffalo didn’t get much out of Stauber and Huddy, but Zhitnik played in Buffalo for nine seasons in the NHL.

#2 Kris Versteeg to Flyers (2011)

The Flyers were in the buyer's market after making the NHL Stanley Cup final in 2010. Kris Versteeg was the big acquisition from the Maple Leafs as a late-season rental. Versteeg scored a couple of goals before Philly crashed out of the playoffs. The Leafs got a first and third-round pick in return. The third-round pick ended up being Josh Leivo, who was a key contributor for the Leafs until 2019. Leivo currently plays for the Blues.

#1 Tyler Toffoli to Flames (2022)

Just last season, Tyler Toffoli was dealt to the Flames in the trade that kicked off the 2022 NHL trade season. The Canadiens received a king's ransom in return: Tyler Pitlick, a first-round pick, and a fifth-round pick. Already in 2023, Toffoli has nearly one point per game.