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Trade Deadline Rewind: Who won and who lost five headline-making deals from the past?

Hindsight is 20/20, right? Let’s look at who won some of the most impactful deals from the past 25 years.

FIVE YEARS AGO

NEW YORK RANGERS ACQUIRE: Martin St-Louis
TAMPA BAY LIGHTNING ACQUIRE: Ryan Callahan, 2014 conditional second-round pick, 2015 first-round pick

Plucked off the scrap heap before becoming the greatest player in franchise history – one who played nearly 1,000 games in Tampa Bay, set numerous franchise records and wore the ‘C’ – Martin St-Louis seemed destined to end his career as a member of the Lightning. But any chance St-Louis and the Lightning had at a storybook ending fell apart when Tampa Bay GM Steve Yzerman, serving in his post as architect of the 2014 Canadian Olympic team, left the 38-year-old winger off the club. The prideful St-Louis was stung, and despite later being named to Team Canada as an injury replacement, a trade request followed the perceived snub.

With a full no-movement clause in place, St-Louis controlled his destiny and sought a deal to the Rangers. The Lightning made the most of their limited trade options by swinging a captain-for-captain exchange that brought Ryan Callahan and a pair of conditional draft picks to Tampa Bay.

Adding St-Louis nearly pushed the Rangers over the top. They rode the Hall of Famer’s playoff experience to a berth in the 2014 Stanley Cup final before a heartbreaking loss to the Los Angeles Kings. St-Louis made noise the next season, too, with a 21-goal, 52-point campaign, and he helped New York make another run to the conference final. His time with the Rangers was brief, however, as he retired following the 2014-15 campaign.

Though trading St-Louis could’ve been a no-win proposition, Tampa Bay came out the long-term winner. Callahan has become a contributing fourth-line piece, though his cap hit has been a thorn in the Lightning’s side. Meanwhile, the conditional picks were later flipped for two picks apiece in their respective drafts, with the Bolts using those selections to land promising prospects Dominik Masin, Mitchell Stephens and Anthony Cirelli, the latter of whom has impressed in his first full big-league campaign.

TEN YEARS AGO

PITTSBURGH PENGUINS ACQUIRE: Bill Guerin
NEW YORK ISLANDERS ACQUIRE: 2009 conditional fifth-round pick (became third-rounder, Michael Lee)

One year removed from falling in the final, the Penguins were in peril of missing the 2009 post-season. Some in Pittsburgh were calling for a blockbuster, desperate to load up and give Sidney Crosby and Evgeni Malkin some support. As far as weapons went, though, a 38-year-old Guerin barely registered. In fact, all the Penguins had to give up was a fifth-round pick that would become a fourth if they made the playoffs and a third if they managed to win a round. As it turns out, the Isles should’ve added more conditions. Guerin gelled immediately and posted a career-best seven goals and 15 points in the playoffs as the Pens captured the first Cup of the Crosby-Malkin era.

The Isles flipped the pick to the Coyotes for a 2010 third-rounder (Jason Clark). Neither goalie Lee nor Clark played an NHL game.

FIFTEEN YEARS AGO

MONTREAL CANADIENS ACQUIRE: Alexei Kovalev
NEW YORK RANGERS ACQUIRE: Jozej Balej, 2004 second-round pick (Bruce Graham)

An enigmatic performer whose talent was said to sometimes far exceed his effort level, Kovalev was a polarizing figure. But the Canadiens needed additional scoring, and Montreal was quick to snap up the winger from the basement-dwelling Rangers, who were willing to offload the crafty winger for a song. Kovalev’s immediate impact was zilch in Montreal, but he rose to the occasion with six goals and 10 points in 11 playoff games in 2004 before the Canadiens exited in the second round. His lasting influence would be more significant, however, as he scored 103 goals and 264 points across 314 games in Montreal, adding another 17 goals and 31 points in 33 playoff outings.

What became of Balej and Graham? The former played 13 games for the Rangers and was out of the NHL by 2006, while the latter never stepped foot on NHL ice.

TWENTY YEARS AGO

DETROIT RED WINGS ACQUIRE: Chris Chelios
CHICAGO BLACKHAWKS ACQUIRE: Anders Eriksson, 1999 first-round pick (Steve McCarthy), 2001 first-round pick (Adam Munro)

An era was already winding down in the Windy City with the Blackhawks trading Jeremy Roenick to the Phoenix Coyotes and Ed Belfour to the San Jose Sharks, but the final nail in the coffin – the admittance that dark days were indeed ahead in Chicago – came when captain Chris Chelios was shipped to the Red Wings. The return was considered to be suspect when the trade occurred, and the passage of time hasn’t helped matters. A bad deal at the time is a bad deal in retrospect.

Chelios, who was 37 when he joined the Wings in 1999, finished sixth in Norris Trophy voting his first full season in Detroit and second in his third campaign. He was a top-pairing fixture into his early 40s and captured two Stanley Cups with the Red Wings. Eriksson spent only one full season in Chicago, while McCarthy and Munro spent their careers on the fringe of the NHL.

TWENTY-FIVE YEARS AGO

NEW YORK RANGERS ACQUIRE: Stephane Matteau, Brian Noonan
CHICAGO BLACKHAWKS ACQUIRE: Tony Amonte, rights to Matt Oates

Matteau’s double-OT winner against the New Jersey Devils in Game 7 of the 1994 Eastern Conference final, a tally met with a cry of “Matteau! Matteau! Matteau!” from play-by-play man Howie Rose, is one of the greatest goal calls in NHL history. But were it not for a deadline deal between the Blackhawks and Rangers, the call wouldn’t exist, and it’s possible New York wouldn’t have ended its 54-year Cup drought.

In a trade the likes of which has gone the way of the dodo, two playoff-bound clubs swung a 2-for-1 swap that addressed respective needs. New York flipped then-23-year-old Amonte to Chicago for Matteau, 24, and Noonan, 28, to bolster their bottom-six. The results were immediate in New York, while Amonte went on to become a star in Chicago, scoring 268 goals and 541 points in 627 games during his tenure as a Blackhawk.

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