Nine Biggest Trade Deadline Deals in NHL History

Dan Falkenheim
Sports Illustrated
With Monday fast approaching, we rewound the clock to look back on some of the major blockbusters trades to happen leading up to the deadline.
With Monday fast approaching, we rewound the clock to look back on some of the major blockbusters trades to happen leading up to the deadline.

The Columbus Blue Jackets initiated trade deadline madness on Friday, sending prospects and picks to the Ottawa Senators for Matt Duchene. Mark Stone is still on the table and Feb. 25 has the potential to be the most seismic deadline in recent memory.

With Monday fast approaching, we rewound the clock to look back on some of the major blockbusters trades to happen leading up to the deadline. Factoring in players involved, the stages of the players’ careers and the position of the teams in the standings, here are the biggest deadline trades in NHL history:

1. Hartford Whalers Say Goodbye to Ron Francis (March 4, 1991)

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Pittsburgh Penguins acquire: Ron Francis, Ulf Samuelsson, Grant Jennings
Hartford Whalers acquire: John Cullen, Zarley Zalapski, Jeff Parker

Ronnie “Franchise” was the heart and soul of the Hartford Whalers. Francis joined the Whalers as the fourth overall pick, an 18-year-old going into the franchise’s third season. He became the team’s captain at 21 years old, led the Whalers to five consecutive playoff appearances and tallied 821 points in 10 seasons. But, unprompted, the Whalers moved on.

The Penguins sent John Cullen (who had 94 points in 65 games that season), Canadian Olympic defender Zarley Zalapski and Jeff Parker to Hartford for Francis, Ulf Samuelsson and Grant Jennings. Francis and the Penguins proceeded to win the Stanley Cup that season, and won again in 1992.

2. St. Louis Blues Acquire Brett Hull (March 7, 1988)

St. Louis Blues acquire: Brett Hull, Steve Bozek
Calgary Flames acquire: Rob Ramage, Rick Wamsley

One Hart Memorial Trophy and 700-plus goals later, it’s easy to call Calgary’s decision to deal Brett Hull one of the most lopsided trades in NHL history. But at the time—Hull was a rookie—there were concerns regarding his skating ability, and then-coach Terry Crisp benched the 23-year-old numerous times. The Flames were on pace to have the best season in team history—they had just lost in the Stanley Cup two years prior—and they received a top-pairing defenseman in Rob Ramage and backup goaltender Rick Wamsley in the trade.

The Flames would win their first Stanley Cup the following season, but failed to make it past the first round of the playoffs in the next 14 consecutive seasons. Hull, meanwhile, nearly toppled Wayne Gretzky’s single-season goal record, helped the United States win the World Cup of Hockey in 1996 and won two Stanley Cups.

3. Coyotes Send Keith Tkachuk to St. Louis (March 13, 2001)

St. Louis Blues acquire: Keith Tkachuk
Phoenix Coyotes acquire: Michal Handzus, Ladislav Nagy, 2002 first-round pick, rights to Jeff Taffe

The St. Louis Blues posted their best regular season in franchise history during the 1999–00 season, but they became the second NHL team to win the Presidents’ Trophy to get eliminated in the first round. Sitting in third place in the Western Conference at the deadline, the Blues traded for three-time All Star and nine-year veteran Keith Tkachuk. Tkachuk provided the Blues a mixture of leadership, physicality and skill, helped avenge the team’s 2000 playoff loss to the Sharks and lead the Blues to their first conference final.

4. Dallas Stars, New Jersey Devils Swap Pieces (March 19, 2002)

Dallas Stars acquire: Jason Arnott, Randy McKay, 2002 first-round pick
New Jersey Devils acquire: Jamie Langenbrunner, Joe Nieuwendyk

Less than two years after the New Jersey Devils defeated the Dallas Stars in the 2000 Stanley Cup, the Stars went out an acquired the guy who scored the double-overtime, Cup-clinching goal against them. Jason Arnott formed the middle of the Devils A-line (alongside Patrik Elias and Petr Sykora) led the team to back-to-back Stanley Cup appearances and scored 97 goals during his five-year tenure. Still, then–GM Lou Lamoriello opted for a change and traded Arnott, Randy McKay and a first-round pick to the Stars for Jamie Langenbrunner and Joe Nieuwendyk.

The trade stung for Devils’ fans but the team would win its second Stanley Cup 2003, with Langenbrunner and Niewendyk playing sizable roles.

5. Vancouver Canucks Trade Away Roberto Luongo (March 4, 2014)

Florida Panthers acquire: Roberto Luongo, Steven Anthony
Vancouver Canucks acquire: Jacob Markstrom, Shawn Matthias

Goaltender Roberto Luongo said he was “stunned” when Vancouver shipped him back to the Florida Panthers—where he started his career. Luongo cemented his legacy in Vancouver, bringing the Canucks to within one game of their first Stanley Cup victory along with setting franchise records in every statistical category, but the then-34-year-old appeared to be declining and was on a bad contract. After trading Cory Schneider less than nine months earlier, the Canucks moved Luongo and Steven Anthony to Florida for 24-year-old goaltender Jacob Markstrom and center Shawn Matthias.

6. Islanders Complete the Puzzle with Butch Goring (March 10, 1980)

New York Islanders acquire: Butch Goring
Los Angeles Kings acquire: Bill Harris, Dave Lewis

The New York Islanders slowly assembled the pieces that would form the core of their dynasty—Bryan Trottier, Denis Potvin, Mike Bossy and Clark Gillies—but they fell short, reaching and losing in the NHL semi-finals four out of five years between 1975 and 1979. GM Bill Torrey wanted a second-line center, and he acquired Butch Goring from the Los Angeles Kings in exchange for veterans Billy Harris and Dave Lewis.

Goring and the Islanders went unbeaten the rest of the regular season and went on to win their first Stanley Cup. Then they won three more in a row, and Goring won the Conn Smythe Trophy in 1981. The trade is held up as the prototypical deadline deal for teams looking for that last “missing piece.”

7. End of an Era in Tampa Bay (February 26, 2008)

Dallas Stars acquire: Brad Richards, Johan Holmqvist
Tampa Bay Lightning acquire: Jussi Jokinen, Jeff Halpern, Mike Smith, 2009 fourth-round pick

The Tampa Bay Lightning’s big three—Vincent Lecalvier, Martin St. Louis and Brad Richards—propelled the franchise its first Stanley Cup in 2004, but then the lockout hit. The Lightning scraped by and were booted in the first round two consecutive years and eventually, in 2008, they decided to split their core. Tampa traded Brad Richards and Johan Holmqvist to the Dallas Stars for Jeff Halpern, Jussi Jokinen, Mike Smith and a 2009 fourth-round pick, and missed the playoffs for the first time since 2002.

8. Rangers Acquire Pavel Bure (March 18, 2002)

New York Rangers acquire: Pavel Bure, 2002 second-round pick
Florida Panthers acquire: Filip Novak, Igor Ulanov, 2002 first-round pick, 2002 second-round pick, 2003 fourth-round pick

Gretzky was the first pricey acquisition by the New York Rangers in the years after their Stanley Cup victory, but he wasn’t the last. The Rangers traded Igor Ulanov, Filip Novak, and their first- and second-round picks in the 2002 draft to the Panthers for Pavel Bure, who was almost 31 years old with a deteriorating right knee. Bure was never fully healthy and failed to return to elite form. The Russian Rocket scored 31 goals in 51 games with the Rangers and never played again after the 2002–03 season.

9. Chris Chelios Heads to Detroit (March 23, 1999)

Detroit Red Wings acquire: Chris Chelios
Chicago Blackhawks acquire: Anders Eriksson, 1999 first-round pick, 2001 first-round pick

Chris Chelios spent eight years with the Blackhawks and had said he “hated” the Red Wings and would never play for them. That changed, though, when a no-trade handshake agreement with Blackhawks owner Bill Wirtz fell through and GM Bob Murray sent Chelios to Detroit for defenseman Anders Eriksson and two first-round draft picks. The Blackhawks fell into cellar-dwelling oblivion while Chelios played another 10 years with the Red Wings and won two Stanley Cups.

Honorable Mentions: Ryan McDonagh to the Tampa Bay Lightning (2018), Kevin Shattenkirk to the Washington Capitals (2017), Martin St. Louis to the New York Rangers (2014), Ray Bourque to the Colorado Avalanche (2000), Markus Naslund to the Pittsburgh Penguins (1996), Stephane Matteau to the New York Rangers (1994).

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