Cynics love to complain about how the NHL regular season is meaningless, but for teams battling for a playoff spot, every game from now until the end of the season is huge. Every night, teams shuffle up and down the standings fighting to finish in the top eight in their respective conferences.

The season ends April 7, but a much more immediate date looms for many teams: the NHL trade deadline on Feb. 27. As a result, teams are busily assessing whether they’ll be buyers or sellers. Meaning teams that are Stanley Cup contenders are looking to pick up that last piece of the puzzle that will put them over the top, teams that think they could be Cup contenders are gambling that a big trade will make them contenders and teams that are rebuilding or out of the race entirely look to unload players with big contracts in exchange for prospects or draft picks. Another factor is pending free agency; players who are unrestricted free agents are able to sign with another team with no compensation to the former team, so those teams often look to get something in return before it’s too late.

There are plenty of big names rumored to be switching teams on deadline day (or before it): Jeff Carter of Columbus, Ryan Getzlaf of Anaheim, Shea Weber of Nashville, Jarome Iginla of Calgary, Ryan Miller of Buffalo and many others. Whether any or all of these players actually get traded is another story altogether, but it makes for great speculation.

Deadline day is practically a national holiday in Canada, where interest in the NHL is naturally through the proverbial roof. The big sports networks in Canada—TSN (which is owned by ESPN), Sportsnet, Score—will all have nonstop trade coverage on Feb. 27 until 3 p.m., which is when the deadline officially hits. Although many trades aren’t announced until after the deadline.

Historically, the vast majority of deadline deals turn out to be busts or insignificant. But there have been some key trades over the years that have directly contributed to a team winning the Stanley Cup:

  • 1991: Pittsburgh acquires Ron Francis, Ulf Samuelsson and Grant Jennings from Hartford for John Cullen, Jeff Parker and Zarley Zalapski. Cullen was a gifted young scorer, but Ronnie Franchise was the piece that the Penguins needed alongside Mario Lemieux, Jaromir Jagr and Tom Barrasso to propel them to their first of two straight Cups.
  • 1980: The New York Islanders acquire Butch Goring from Los Angeles for Billy Harris and Dave Lewis. The Isles were stocked with young talent but had suffered early playoff exits for a few years until grizzled vet Goring provided the clutch scoring and leadership that was missing. That spring, the Islanders won their first of four consecutive Cups and Goring even won the Conn Smythe as playoff MVP in 1981.
  • 1988: Edmonton traded goalie Andy Moog to Boston for Geoff Courtnall, Bill Ranford and a draft pick. The trade helped both teams, as Moog gave the Bruins a solid goalie tandem alongside Reggie Lemelin, but the Oilers won their fourth straight Cup in ’88 over the Bruins with Ranford as backup, and then would defeat Boston again two years later with Ranford as the starter.
  • 2003: New Jersey trades Jason Arnott and Randy McKay to Dallas for Jamie Langenbrunner and Joe Nieuwendyk. The deal paid immediate dividends for the Devils, who won the Cup that year.

There are plenty of other deals that have paid off down the line as draft picks turned into future stars. And of course, there were trades that did absolutely nothing for the teams involved. Such is the risk and the allure of the NHL trade deadline.

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