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The Five: Worst NHL Trade Deadline Deals By Red Wings

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Kyle Quincey, ex-Red Wings
In 2012, the Red Wings traded a first-round pick to Tampa Bay for Kyle Quicney. Tampa Bay turned that draft pick into Andrei Vasilevskiy.

What the Detroit Red Wings roster look like at the end of the day Monday? Well, for certain it will be different.

Come 3 p.m. Eastern Time Monday afternoon, every GM in the NHL will confidently pronounce how thrilled they are with the oulook of their teams post trade deadline. Fan bases will be mentally plotting Stanley Cup parade routes.

All will be quietly of the belief that their team is improved.

In fact, the majority of them will be proven incorrect.

The NHL trade deadline is a lot like elite baseball sluggers. For every connection, there are several swings and misses. An NHL team capable of going .300 in all-time trade deadline moves is doing quite well.

Red Wings fans like to remember the hits but the fact of the matter is there’s also been many misses. On deadline day, these moves seemed like the right idea at the time. Instead, they blew up in spectacular failure and some of them continue to haunt Detroit to this day.

These are the five worst NHL trade deadline deals made by the Red Wings

Feb. 21, 2012 –  Red Wings traded Sebastien Piche and a 2012 first-round draft pick (Andrei Vasilevskiy) to the Tampa Bay Lightning for Kyle Quincey

That Ken Holland felt Quincey was worth a first-round pick is a head scratcher. The fact that it was then Tampa Bay GM Steve Yzerman who fleeced the Wings probably made it hurt even worse.

And twice Detroit fans were watching as Andrei Vasilevskiy, the goalie claimed with that No. 1 pick, backstopped the Bolts to the Cup. He’s also won a Vezina and a Conn Smythe along the way.

March 8, 1994 – Detroit traded Tim Cheveldae and Dallas Drake to Winnipeg Jets for Bob Essensa and Sergei Bautin

Cheveldae wasn’t the answer for the Red Wings in goal but neither was basically trading Cheveldae for Cheveldae. Essensa wasn’t an upgrade between the pipes and he certainly wasn’t the Essensa goaltending.

He lost his job in the opening playoff round to rookie Chris Osgood as the Wings were ousted by San Jose.

March 5, 2014 – Red Wings traded Patrick Eaves, Calle Jarnkrok and a 2014 second round draft pick (Julius Bergman) to Nashville Predators for David Legwand

The Seattle Kraken recently got three draft picks from Calgary in exchange for Calle Jarnkrok. All the Wings were capable of acquiring for him was a washed-up David Legwand.

Mind you, the Wings were desperate. They were missing the first four centers on their depth chart. The playoffs weren’t a guarantee and Holland was operating under instructions to maintain Detroit’s streak of postseason appearances at all costs. In 26 games as a Red Wing, Legwand scored four goals – none of them in the playoffs as Detroit was bouncing out to Boston in five games.

March 1, 2015 – Detroit traded Mattias Backman, Mattias Janmark-Nylen and a 2105 second-round draft pick (Roope Hintz) to the Dallas Stars for Erik Cole and a 2015 third round draft pick (Vili Saarijarvi)

A neck injury brought about the end of Cole’s NHL career after 11 games in Detroit. Meanwhile, both Janmark and Hintz ended up helping Dallas to the 2020 Stanley Cup final. Hintz is a two-time 20-goal scorer.

March 23, 1999 – Red Wings acquired Ulf Samuelsson (New York Rangers), Wendel and Bill Ranford (Tampa Bay Lightning)

It was looking like an epic trade deadline day when the two-time defending Stanley Cup champion Wings were adding this trio along with Norris Trophy-winning defenseman Chris Chelios. By the start of the next season, only Chelios was still with Detroit.

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Injuries limited Samuelsson to 13 games. Clark scored just twice in the playoffs. Things went south for the Wings in the second round against Colorado when Ranford replaced an injured Osgood in goal. Detroit squandered a 2-0 series lead and lost in six games.

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