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A tip of the cap to Leaking 5w-30, who got me thinking about some of the best and worst trades in the history of the Edmonton Oilers with his question in today’s edition of the Monday Mailbag.

I’ve narrowed it down to what I consider the best five trades and the worst three, but there’s obviously many more in both categories that are worthy of debate – especially when you follow the trade tree of some swaps from the initial deal to subsequent acquisitions made with players involved. I’m sticking to the initial trades.

While there’s still plenty of discussion, as you’d expect, about the deal GM Peter Chiarelli just made that sent Taylor Hall to the New Jersey Devils for Adam Larsson, you won’t find it listed because it’s too soon to know how it’s going to turn out. Likewise, I didn’t find any other move by Chiarelli worthy of inclusion on the best or worst trades based on the early returns.

Craig MacTavish and Steve Tambellini didn’t make the list either, even though they had their moments, good and bad, during their tenures in the big chair. In the end, Glen Sather trades show up six times on the lists and Kevin Lowe owns the other two spots. You, of course, might see it differently, but here’s what I came up with.


Thumbs Up

Edmonton Oilers acquire


New York Rangers acquire

Doug Weight

March 17, 1993 

Esa Tikkanen

If ever there was a case of “out with the old, in with the new,” Sather pulled it off by swapping proven warhorse Esa Tikkanen for Doug Weight, who would become Oiler captain and the team’s best player for many years while Tikkanen faded away. Weight, just 22 when acquired, would play 588 regular season games over parts of nine seasons in Edmonton and would score 157-420-577. He’d add 10-23-33 in 39 playoff games. Tikkanen, 28 at the time of the trade, bounced around to six teams during the rest of his career. He did win a Cup with the New York Rangers in 1994, but never replicated the personal success he enjoyed in Edmonton.

Toronto Maple Leafs acquire


Edmonton Oilers acquire

1999 4th round pick (#110-Jonathan Zion) 
2000 2nd round pick (#51-Kris Vernarsky)

March 23, 1999

Jason Smith

If you can tell me what became of Jonathan Zion and Kris Vernasky, who were the draft picks the Maple Leafs got from the Oilers for Jason Smith without Googling them, you’re one up on me. Nobody needs a search engine to know what Smith meant to the Oilers in the 542 games he spent with Edmonton. Smith took over the captaincy from Weight after he was traded to St. Louis and he wore the C for five seasons, tying Wayne Gretzky as longest serving captain in franchise history. Tough as nails and mean as hell was Smith. A leader of men.

Edmonton Oilers acquire


St. Louis Blues acquire

Curtis Joseph rights to Mike Grier

August 4, 1995

1996 1st round pick (#14-Marty Reasoner)

1997 1st round pick (#15-Matt Zultek)

Simply put, the man fans called Cujo came billed as the shot in the arm the post-Stanley Cup era Oilers needed in the crease and he delivered in spades. Before Cujo left Edmonton for stacks of cash in Toronto, he spent 201 games between the pipes and provided countless highlights – none bigger than his ridiculous save on Joe Nieuwendyk that set the stage for Todd Marchant’s Game 7 winner in a stunning upset over Dallas in 1997. And the rights to Mike Grier? That turned out pretty well, too.

Edmonton Oilers acquire


Detroit Red Wings acquire

Adam Graves

Petr Klima

Joe Murphy

Jeff Sharples

November 2, 1989

Jimmy Carson

Kevin McClelland

1991 5th round pick (#100-Brad Layzell)

Jimmy Carson, the big piece coming back from Los Angeles in the Wayne Gretzky trade/sale, didn’t want to be here. Klima, for all his inconsistencies and off-ice distractions, scored the winning goal in triple-overtime of Game 1 of the Stanley Cup final in 1990. Graves and Murphy were two-thirds of the Kid Line with Martin Gelinas.

Edmonton Oilers acquire


St. Louis Blues acquire

Chris Pronger

August 2, 2005

Eric Brewer

Doug Lynch

Jeff Woywitka

Sure, there’s no getting around the fact Chris Pronger’s trade request and departure after the Oilers went all the way to Game 7 of the 2006 Stanley Cup final played a huge part in the decline the Oilers have been on since then. Let’s not forget, though, Pronger played his backside off in the 80 regular season and 24 playoff games he spent here. Pronger played 27:59 per game during the regular season and a whopping 30:57 in the post-season. He was an absolute stud. There wouldn’t have been a 2006 playoff run without the Human Rake.



Los Angeles Kings acquire


Edmonton Oilers acquire

Wayne Gretzky

Mike Krushelnyski

Marty McSorley

August 9, 1988

Jimmy Carson

Martin Gelinas

1989 1st round pick (#18-Jason Miller)

1991 1st round pick (#20-Martin Rucinsky)

1993 1st round pick (#16-Nick Stajduhar)


You don’t trade/sell the best player in the history of the NHL before his 28th birthday and win the deal, but that’s what Sather did with owner Peter Pocklington pulling the strings. Carson couldn’t get out of Edmonton fast enough, Gelinas was a good player but never a great one and the three draft picks the Oilers got from L.A. turned into Jason Miller, Martin Rucinsky and Nick Stajduhar. Hard to say for sure where the $15 million Pocklington got ended up. Many Oiler fans insist to this day there’s a special place in hell waiting for Pocklington because of this deal.

Buffalo Sabres acquire


Edmonton Oilers acquire

Miroslav Satan

March 18, 1997

Craig Millar

Barrie Moore

Miroslav Satan was only 22 when Sather and the Oilers decided they couldn’t or wouldn’t reward him with a substantial raise in a new contract after a 25-goal season. Sather instead shipped him to Buffalo. Satan’s career would span 1,050 games and he’d score 328 more goals after leaving Edmonton. Millar played 36 games with the Oilers and Moore played a total of four. Both were out of the NHL by the age of 24. Hell no.

Edmonton Oilers acquire


New York Islanders acquire

Robert Nilsson

Ryan O`Marra

2007 1st round pick (#15-Alex Plante)

February 27, 2007

Ryan Smyth

As if the tearful scene at the airport wasn’t bad enough after Lowe refused to bump up his offer by $100,000 a season and do a deal with Smyth and agent Don Meehan, he also got a whole bunch of nothing back from the Islanders in the trade after digging in his heels and setting up the dramatic exit of No. 94. Smyth could have and should have spent his entire career in Edmonton.

Listen to Robin Brownlee Wednesdays and Thursdays from 3 p.m. to 5 p.m. on the Jason Gregor Show on TEAM 1260.


    • Explicit

      That was a fun read! I looked back at the 2007 draft to see if that Smyth trade could’ve looked any better with a different pick, man that was a bad draft all around. Would of been a whole different oilers team with Voracek, Ian Cole and Pacioretty instead of Gagner, Plante and Nash. But Im going to like my McDavid era!

    • oilman3

      If the Oilers are so terrible and nobody wants anything to do with them, then kindly explain why people like yourself hang around so anxiously waiting to comment on a site devoted to the team. Also, we had bonafide superstars who loved being here and were very emotional when they left. Calgary…not so much.

      • OTOF2

        Unlike Calgary, most of the past Oil stars left the city when the pay cheques stopped coming and never returned. Just off the top of my head;
        Gretzky- far far away, Messier- far away, Coffey- far away, Kurri- far away.
        Lanny McDonald- still lives in Cgy, Mike Vernon – still lives in Cgy, Theo Fluery – still lives in Cgy, Jim Peplinski- still lives in Cgy. Hmmm.

        • Cowbell_Feva

          4 players live in Calgary…out of how many hundred over the years.

          Let’s not get all ridiculous and think that Cowtown is some ultra city with people clambering over each other to get to it.

          Southern California or Florida sure, but Calgary? Ummm no.

        • Randaman

          I lived in Calgary for many years. It has a lot of good points. I grew up in Edmonton so I am bias.

          Vernon is from Calgary so that is understandable. He’s a well known figure and enjoys the city.

          Lanny has a god complex and enjoys all the perks that go with that.

          Peplinski has been highly successful in the truck leasing business and has been ripping off Calgarians for many years. Why would he leave.

          Fluery seems to have straightened his life out and has kids in Calgary.

    • Shameless Plugger

      Who……tell me who is or has flocked to the dump known as the saddledome?

      Is there nothing exciting to talk about at Lames nation? Oh wait there is the monumental signing of Troy Brouwer. Woooooo talk about landing the big fish.

      Open your eyes, the past two years the top free agents have chosen Edmonton. Your post is three years late.

      • Serious Gord

        Two years out of 25-30. And the attraction isn’t EDM – it’s McD. Players wanted out of here/didn’t want to come in part because EDM is one of the least attractive cities in the league and the most remote media market. But a bigger part IMO for many was the Management and ownership. That may have changed for the better – it couldn’t get much worse. Time will tell if it really has.

        • HardBoiledOil 1.0

          UFA’s aren’t signing in Cal-Gary because it’s a beautiful city or anything like that. they are signing for money and term because that team isn’t winning anything soon.

          • Serious Gord

            Calgary is a (slightly) bigger media market and percieved as a nicer city by most rich outsiders – mountains, chinooks and more self-made wealthy people. And a less disastrous management group (not perfect to be sure).

            Accept the reality.

        • Oilerchild77

          I agree. Pocklington’s name was mud around the league. And, at the time, Edmonton was not a good media market. But the world has changed since then. A player and organization can market themselves from anywhere now. We don’t live in a TV world anymore, we live in the online world and the size of a market is much less important than it once was.

          • Serious Gord

            The world has changed somewhat.

            However the status of the oil had changed very little until McD and the new arena dawned. It remained very low on the list of desirable places in the league if you remove those to very very event factors.

            And online isn’t here yet but clearly regional dynamics will still hold a lot of sway and EDM will relatively be a very small media market and thus secondary income source compared to a majority of the league.

          • Oilerchild77

            Online isn’t here yet? You’re online right now. Online is very much here, and here to stay. My point is, you don’t need to play in New York or LA to get worldwide exposure anymore. Anyone can google Connor McDavid and watch all his highlight reels. Fans can see any game, any time online with a cable subscription. This wasn’t the case in 1988 when Gretzky was traded. The NHL needed him in a major media market like LA to get Gretzky and the league the exposure it needed.

          • Serious Gord

            Still the vast majority of viewers are on conventional TV. And yes you can watch every minute a player plays – live – online. And in fantasy football fans often watch every minute of every game sometimes when the game is completely meaningless and in another market.

            So yes players can monetize their careers better than they could regardless of where they play.

            But the big markets are where the really big money is for star players. Which is why Lebronwill leave Cleveland in a year (again) and the Timberwolves are Siberia.

            Ask Robinson cano if he thinks going to Seattle was the best financial move in hindsight.

            Players want to play for winning franchises or big market franchises – especially star players. EDM may be on track for the latter. But will never be one of the former.

          • Oilerchild77

            Well ok. I see your point. Yes some players will always choose the bright lights of the major markets, but Lebron doesn’t need a New York, markets like New York need him. Same goes for McDavid. The money he will make in Edmonton will be the same, especially in the cap era. As for the endorsements, he’s getting those as well regardless of playing in Edmonton.

          • Oilerchild77

            I seriously doubt that. When you’re as dominant a player as Lebron, it doesn’t matter where you play. Take a look at the endorsement money he gets. It’s astronomical. Being a Knick would change nothing.

        • But the BIGGEST part IMO was Management and Ownership.Fixed that for you, The dam is starting to break , but I would bet there are still agents and players who wont come here until the stench the sycophants have left on this franchise is removed by their outright dismissal.It is justified and there is no way to actually defend their record.

    • Oilerchild77

      Quite right, but the stanley cup the Oilers won the following year eased the pain.

      Btw. Calgary is not exactly a player’s first choice either bud. Also, I seem to recall the most prized dman last offseason and the most coveted forward signing this season in Edmonton the last two years. Huh…that’s wierd…it’s almost as if Edmonton was a desired location for some free agents.

  • ¯\_(ツ)_/¯

    Messier to the Rangers for Louie DeBrusk, Bernie Nicholls, and Steven Rice was pretty bad ROI. Really it’s Messier for Nicholls with Rice playing in the AHL for two years before going to the Whalers.

    Kurri for a year in postcards from Italy to end up in LA was pretty sad, as well.

  • a lg dubl dubl

    I forgot about Stajduhar. Read up on him on Wikipedia, to bad about that incident at a bar in Cape Breton, even if his attitude was questionable on the ice.

    Still think the Comrie to Anaheim trade was a HUGE face palmer even if it didn’t actually go through.

    • ubermiguel

      That Comrie situation was perhaps the stupidest non-trade trade in the history of sports. Way to let ego get in the way 6 Rings. Still, that Pronger deal…

      • It was a vindictive move by Lowe in a situation that became painfully personal between the sides. I’ll never forget how stunned Bryan Murray sounded on the phone when I called him to find out the details of what happened.

        • Explicit

          What happened again? Was it Perry and a first for Comrie, then Lowe just decided he wanted Comrie to pay the oilers a million dollars or somthing. Anyone remember what that first round pick was? Then they ended up trading him for Woywitka and the Schremp pick. Did Lowe ever get his money from Comrie?

        • Another in an extremely long list of examples where Lowe lets his ego get in the way of doing what is best for the team. I seem to remember a certain player(#4) buggering off to the New York Rangers for an extra $100,000.00. Should have kept Smytty and sent Lowe to New York instead. Maybe he would learn something if his arrogance and ego would get out of the way.I’m sure Sather would have told him he is not suited to the job.

      • Seanaconda

        Mactavish was joking. He always had the best lines when he did his pre and post games.

        One of my favorites is when a player was trying to play net while the goalie was out and he got scored on 5 hole and his post game was ‘everyone knows always go 5 hole on (player)’ sorry can’t remember the name. Mactavish was sarcastic as heck most interviews

        But it will be forever remembered as he thought Marty was as good as Sakic but slow.

        But anyways reasoner was actually a decent 3rd liner his entire career.

        • Spydyr

          He was being serious. It was quoted in the MSM.It has even been mentioned on articles here.

          “One of the first signs there wasn’t something quite right with then Oilers Coach Craig MacTavish was when he likened NHL depth Center Marty Reasoner to All-Star Joe Sakic. Check this piece for the whole context but the money line is “If Marty had more speed, he’d be Joe Sakic.” It’s actually impossible to be further apart than Marty Reasoner and Joe Sakic. Marty Reasoner was basically playing the role of Boyd Gordon for the Oilers the year of that quote. It would be effectively saying that a less physical Boyd Gordon was a better stride away from being Malkin. I guess it probably made Reasoner feel nice for a second, but in the long run it just makes both parties the punch line of a joke. ”

          • Seanaconda

            When he was talking about reasoner he had his stupid smirk a twinkle in his eye and was laughing. The shultz thing he was serious and that ended up being horribly wrong.

            But really can people only be serious 100 percent of the time or joking 100 percent of the time ??? I’ll give you the shultz but the Sakic thing he was being cheeky idk if you watched the oilers when he was the coach but he was always being sarcastic and joking around. He should of stayed a coach tho. I’m suprised he didn’t get a head coach job after he stepped down and the next season with Pat the oilers dropped to the bottom of the nhl.

  • ubermiguel

    Any time a future hall of famer gets dealt it’s going to hurt. Coffey turned into an ok deal with Craig Simpson coming back. Moog was traded in that deal conditional on him getting signed but that fell through so Moog ended up getting moved for Geoff Courtnall and Bill Ranford which turned into a very good deal. I’d say that was a better deal than the Carson deal. Ranford won the Conn Smythe of course, but he also spent years facing too many shots behind a diminishing club.

  • Hemi

    Looking back at some of the managing of players by Lowe, it is no wonder why the fan base in general, has grown to dislike him so much.

    As a player, Lowe was very much respected by the fans. His association with the Oil’s org after his playing days has for the most part, transferred his status from hero to zero, despite his work outside of hockey with Edmonton charities/etc.

    Go Oil.

  • The Last Of Barrett's Privateers

    This will go down as one of the worst Oilers trades in the history of the team.

    Chiarelli , McTavish & Green trade the 16th OVA and the 33rd OVA for a LHD G. Reinhart.

    The Oilers at this TIME were still looking and were still in need of a RHD, but instead of making a deal for a RND when the Oilers had an abundance of 1st and 2nd round picks blew a deal on another LHD that might never make it into a top four pairing Dman.

    Instead, the Oilers the very next season, deal there second best player and a player who produces in the top 5 in the league at 5×5 for a player who may never be a elite 1st pairing RHD.

      • Shameless Plugger

        How many NHL games have those two picks played?

        Griffin Reinhart is 22….. TWENTY TWO YEARS OLD!

        I’ll give him until he hit a d-mans “coming of” age, say around 24-25. Then judge the trade.

      • The Last Of Barrett's Privateers

        Chiarelli was the Oilers GM for a week when he made that trade, MacTavish, Howson and Green (Reinharts old GM for the Oil Kings) convinced Chiarelli Reinhart was a good bet after TraderPete lost out on Hamonic at the draft that year, this is when Hamonic first requested the trade.

        Since the Oilers lost out on Hamonic and Hamilton they settled on a horrible trade orchestrated by the old regime.

        • RJ

          I remember the hype job when PC came in. “He’s a veteran GM! He won a Cup!”
          If I accept your version, the veteran GM over-reacts when he misses out on two defencemen so he badly overpays for an AHL defenceman who is left-handed, provides zero offence and is not known for moving the puck because MacT and Howson said so? Yeah, ok. That’s what Stan Bowman would have done.

          If MacT and Howson were in favor of something, then I would have pulled a George Costanza and done the opposite. Would have worked out well in this case.

          • The Last Of Barrett's Privateers

            You know you can look this up at Edmonton Right?

            Paraphrasing ” Rienhart is a player I know little about, I’ve seen him only a couple times and he looked good, we had a need for a top four Dman”

            You can think the others never had a hand in the decision, but who knew Rienhart the best?

            The GM that drafted him, the old GM that wanted him, and the person whom the kid billeted with for three years……

            Ya, maybe you’re right though, TraderPete pulled that off all by himself after one week of employment with the same organization that had the same player for three years.

  • Serious Gord

    Robin: thanks for the column and the effort.

    I don’t think the Gretz trade should be viewed in the same light as all the others. Pick had huge off ice motives and were it not for sathers protests it could easily have been a cash deal with no players coming back.

    And I would remind readers that quite a few people thought the Pronger trade was a big win for St. Louis at the time.

  • rockmoss

    Thanks for the great read! The 2 best trades that I liked were the ones made for Weight and Pronger.
    Doug Weight sure could dominate a game and was fun to watch. I always thought he was underrated in NHL circles.
    I am sure that I am in the minority here but I am glad that I was able to watch Pronger play for the Oilers. It sucked when and how he left but that doesn’t take away just how great a player he was. I thought he should have won the Norris trophy that year.

  • Ed in Edmonton 1

    The first deal the Oil made as an NHL teams was on June 9, 1979. The Oil agreed not to make Paul Schmyr a priority selection, thereby allowing the North Stars to acquire his rights. For this consideration the Oil got the North Stars 4th round pick which turned into Glen Anderson.

    • ¯\_(ツ)_/¯

      The second trade they made was pretty good, too.
      August 9th (draft day): To Minnesota: the 42nd (Neal Broten) and 63rd (Kevin Maxwell) pick of the draft; to Edmonton: the 48th (Mark Messier) pick and some guy named Dave Semenko.

  • Ed in Edmonton 1

    Another favorite trade was in 87. the Oil obtained former Flame star Kent Nilsson from the North Stars in a cash transaction. The Flames were paying 1/2 of Nilson’s salary from a previous deal and watched him win a cup with the Oil.

    • Serious Gord

      It was the right move. The return was less than expected but not unreasonable. That Plante was the wrong pick is an ancillary failing on the part of the scouting and klowe.

    • Mark Messier jersey retirement night.

      In a much larger context….. what a complete joke of a move by the organization. Instead of the euphoria of Smyth signed and Lowe prancing out there to love, we had Lowe in hiding, MacT stumbling over Lowe’s speech and the ensuing death march of a season.

      AND THEYRE ALL STILL HERE…. new ownership, true; and Wanye’s Oilers Nation as rebuttal/pain medication… also true.

      But in context….. just wow…. wow, wow, WOW!

  • O.C.

    Side note to Peter’s $15M win fall. He waited on the Gretzky “trade” until just after the season ticket holders had paid their renewals.

    That ticked off a lot of people.

    • HardBoiledOil 1.0

      that was a good move from a business standpoint, but ya it was dirty pool. he knew he’d likely have gotten half of the season’s renewals if he’d traded Gretzky first.

  • Connor McFly

    The only way Lowe, and every Oiler GM since Slats, should be allowed to enter the HOF is to pay their admission first like every other customer. I’l give Chia another year or two to see how he shakes out. Sketchy so far.

    • Serious Gord

      Agreed. The moves chia has made so far have yet to prove out. But they showing desire for a certain style of player and hockey.

      And it could be argued that he is being swayed by Mact and howson (and Lowe?) ok some of them.

      Time will tell whether he is Able to assemble a winning team and one that continues to win once/if he gets there.

  • 99 to 97

    Cheer up guys. Remember when the Flames traded that straight-sticked Doug Gilmore and extras for Gary Leeman and extras to the Leafs? Or future sniper Brett Hull and a sweetener to the Blues for Rob Ramage and back up goalie Rick Wamsly? At least Calgary was a couple years ahead of Edmonton when it came to trading out their talent for shiny bells and whistles.

  • madjam

    Some of best trades came by way of buildings .

    The old Stock Pavilion that opened Xmas day back in 1913 . I’m sure we all remember that day . Called the “Cow Barn” . I guess Calgary still has not progressed beyond that stage . It then was renamed the Edmonton Gardens with girders that obstructed view and dripped water onto playing surface creating mounds on ice during play . 1966 it was renovated and held up to 5,200 fans . It housed our WHA team from 1972-74 , where then we moved into the new building the Northlands Coliseum . We now are poised to go into a new building this year . Calgary still stuck in the saddle .

  • Morgo_82

    Other wins that come to mind:

    Roman Hamrlik and Paul Comrie from Tampa for Jason Bonsignore, Steve Kelly and Bryan Marchment. Hamrlik was by far the best player in this deal and they got him for two failed first rounders and a defenceman on the decline.

    Tommy Salo from NYI for Mats Lindgren and an 8th rounder. Nothing like getting your starting goaltender for the next 4 years for essentially nothing.

    Dwayne Roloson for a 1st and 3rd round picks. No way the Oilers do what they did in the ’06 playoffs without making this move.

    And one of my favourite trades, the return of Ryan Smyth for Colin Fraser and a 7th rounder (so basically nothing). This trade got even better because Dean Lombardi turned into a whiny little b!tch after this deal went down even though he’s the one who accepted it.

    Also, bonus points on the Curtis Joseph trade for the whole thing being initiated by the Blues signing one of the worst players in Oilers history, Shayne Corson.