10 regrettable NHL trade deadline deals

The Pittsburgh Penguins traded James Neal to the Nashville Predators in exchange for Patric Hornqvist and Nick Spaling. (Gregory Shamus/NHLI/Getty)

In the minutes, hours and days leading up to the NHL trade deadline, draft picks and prospects are annually thrown around like Dustin Brown dishes body checks — often. Some trades pan out for the general managers that make the impulse moves while others, well, don’t look so good anymore.

Here are 10 of the most regrettable deals ever made at the trade deadline, in chronological order.

1980: Draft pick turns into Phil Housley

Jerry Korab was a physical defenceman who played his best hockey while with the Buffalo Sabres in the 1970s. At the 1980 trade deadline, the Los Angeles Kings obtained Korab, who was past his prime at the time, in exchange for a first-round pick in the 1982 draft. With that pick, at sixth overall, the Sabres selected Phil Housley, who would go on to play in seven all-star games and flourish as one of the best offensive defencemen during his 21-year NHL run.

1981: Buffalo picks L.A.’s pocket, again

This trade stung Buffalo at the time, as the Sabres shipped fan favourite Rick Martin west. Martin battled injury while with the Kings and played just four games for them before retiring. Meanwhile, the Sabres received another first-round pick from the Kings, this time in 1983. Who did they take fifth overall that summer? A goaltender by the name of Tom Barrasso, who won the Calder and Vezina trophies for Buffalo in 1984 and backstopped Pittsburgh to two Stanley Cups.

1988: St. Louis acquires future Hall of Famer

At the 1988 trade deadline, the Calgary Flames acquired Rob Ramage and Rick Wamsley from St. Louis. Ramage, a quality defenceman, only played two seasons in Calgary, while Wamsley backed up Mike Vernon in net. Both were part of the Flames’ 1989 Stanley Cup team.

In return for Ramage and Wamsley, the Blues received forward Brett Hull — you may have heard of him. Hull was a promising young forward at the time, but his career took off in St. Louis. He had four 100-point campaigns in St. Louis, including an 86-goal season in 1990-91, and he was inducted into the Hockey Hall of Fame in 2009.

1991: Pittsburgh loads up for Cup run, courtesy of Hartford

This may be the king of them all. In 1991, Hartford traded Ron Francis, Grant Jennings and Ulf Samuelsson to the Penguins in exchange for John Cullen, Jeff Parker and Zarley Zalapski.

Francis and Samuelsson were integral pieces of Pittsburgh’s puzzle, helping them win back-to-back Stanley Cups in 1991 and 1992. Francis went on to rack up 1,798 career points, fourth all-time, and was one of the most consistent players in league history.

None of the three pieces that Hartford received were on the roster beyond 1994.

1996: Vancouver steals a future captain

As good as the trade with Hartford looked for Pittsburgh, this one turned out to be the opposite. The Penguins inexplicably dealt youngster Markus Naslund to Vancouver in exchange for Alek Stojanov. Stojanov only played 45 games with the Penguins over two seasons before fading into oblivion. Naslund, meanwhile, racked up 896 career points, mostly with the Canucks, and had his number retired in Vancouver.

1997: Oilers ship Satan to Sabres

Miroslav Satan, a fifth-round pick of the Edmonton Oilers in 1993, had shown early flashes of brilliance in his first year in the NHL. However, the Oilers decided to deal Satan to Buffalo in exchange for two career minor-leaguers, Barrie Moore and Craig Millar. The trade seemed to spark a fire in Satan, who went on to post three 30-goal seasons in seven-plus seasons with the Sabres.

1999: Buffalo strikes again

The Florida Panthers may not necessarily be kicking themselves over this trade, but it certainly looks bad on paper. They acquired defenceman Mike Wilson from Buffalo at the deadline in 1999 but failed to make the playoffs — and Wilson was out of the organization by 2001. Meanwhile, Buffalo obtained useful blue-liner Rhett Warrener and a fifth-round pick, which it used to select all-star goaltender Ryan Miller 138th overall.

2007: San Jose’s aggressiveness backfires

The San Jose Sharks were Stanley Cup contenders in 2006-07 and looking for a boost. Sharks GM Doug Wilson had two first-round picks to work with and used them in separate trades at the deadline — one to acquire Bill Guerin from St. Louis, the other to acquire Craig Rivet from Montreal. Both were pending free agents.

San Jose didn’t advance past the second round that spring, and those first-round picks were used on David Perron (St. Louis) and Max Pacioretty (Montreal). To make matters worse, Wilson threw in young defenceman Josh Gorges in the trade to acquire Rivet. Gorges is now one of the league’s more steady stay-at-home defencemen.

These two trades — along with the 2008 deadline deal that brought in Brian Campbell but cost them another first-rounder (Tyler Ennis) — caused San Jose to take a step back.

2007: Atlanta trades away Coburn

Atlanta Thrashers GM Don Waddell was desperate at the 2007 deadline as his team was on the verge of its first-ever playoff appearance. Waddell rolled the dice on veteran Keith Tkachuk (that trade made sense). The other one, though, in which the Thrashers acquired Alexei Zhitnik from Philadelphia for Braydon Coburn, did not. Zhitnik did tally 14 points in 18 games for Atlanta late that year, but Coburn was a prized prospect at that time and has been a solid defenceman for the Flyers.

2011: Dallas overpays for Goligoski

Dallas Stars defenceman Alex Goligoski is solid in his own right. However, the package GM Joe Nieuwendyk gave up to acquire him looks brutal today, as he dealt youngsters James Neal and Matt Niskanen to Pittsburgh in the trade. Neal scored 40 goals for the Penguins in 2011-12 and has been one of the most dangerous weapons in Pittsburgh’s arsenal since. Niskanen, too, has improved since going to the Penguins.

It was a steal on the day of the trade, and it’s even more of a steal now.