12 Biggest Deadline Deals (Oilers)

This is Ron Low. A deadline deal that sent the big goalie to Edmonton for Ron Chipperfield was the first of many deadline deals made by the Oildrop. That deal–made just one day after the famous "Goring to the Island" trade–was a very important transaction in Edmonton’s NHL history. Is it one of the 12 biggest deadline deals in Oilers history? Read on.

  • #12: March 11, 1980- Oilers trade C Ron Chipperfield to Quebec for G Ron Low. This is a quite famous trade for two reasons: first, the club badly needed goaltending help at the time and second Chipperfield’s Mom was gravely ill at the time of the trade. Low played well and the young Oilers thrilled the fanbase with an incredible playoff run.
  • #11: March 20, 1996- Oilers trade R Kirk Maltby to Detroit fro D Dan McGillis. This turned out to be a set up deal (McGillis would be sent along a year later at the deadline) but the trade was an excellent one for both teams. The Oilers could use a deal like this one right now.
  • #10: March 6, 1990- Oilers trade D Jeff Sharples to New Jersey for D Reijo Ruotsalainen. Do you remember Ruotsalainen as a player? If you saw him, it was impossible to forget him. People have their favorite memories of this player, but for me it was his incredible passing ability. He was stunning. Anyway, when he arrived in 1990 Ruotsalainen stepped right in and had a major impact on the team’s final successful Stanley run. Beauty player.
  • #9: March 9, 2005: Oilers trade G Tommy Salo and a 6th rd pick in 2005 to Colorado for D Tom Gilbert. A terrific trade that gave the Oilers a bona fide top 4 defender. Although the fanbase is divided in regard to his career value, few Oiler fans can argue that this trade was quality.
  • #8: March 23, 1999: Oilers deal a 2nd (2000) and 4th (1999) round pick to Toronto for D Jason Smith. Helluva timely deal, as Smith was run out of Toronto by Pat Quinn just in time to quickly become a dependable player and leader for the young Oilers. Blood and guts throwback won the hearts of every fan who ever saw him in Copper and Blue.
  • #7: March 24, 1998: Oilers trade D Dan McGillis and their 1998 2nd rd pick to Philadelphia for D Janne Niinimaa. Wonderful deal for the Oilers, Niinimaa gave them his best 5 best seasons in the NHL and still had enough trade value at the end of it to garner Raffi Torres.
  • #6: March 1994: Oilers trade C Craig MacTavish to New York Rangers for C Todd Marchant. The classic trade for a have-not team: deal a quality veteran who contributed to championships for a player who could (and did) replace the veteran for years to come. Lordy. Thanks Slats.
  • #5: March 8, 2006- Oilers trade 2006 1st rd pick and 2007 3rd rd pick to Minnesota Wild for G Dwayne Roloson. A wonderful deal perfectly addressed a strong need and Roloson’s .927 SP during the Stanley run doesn’t begin to reflect his contribution. Will be remembered always for the San Jose save.
  • #4: March 8, 1988- Oilers trade G Andy Moog to Boston for G Bill Ranford, L Geoff Courtnall and Boston’s 2nd rd pick in 1988. The pick didn’t amount to anything at the NHL level, but the payoff was a Conn Smyth goaler and a speed demon. Oilers won that trade going away, but there were an exceptional number of Oiler fans who were devastated by the way Moog’s Oiler career ended. You could say that about a few former Oilers. 
  • #3: March 18, 1997- Oilers trade L Miro Satan to Buffalo for L Barrie Moore and D Craig Millar. Biggest doesn’t mean best, and this one was the worst. Awful deadline deal made necessary because coach Ron Low didn’t see what Miro Satan would become. What a bad deal. I feel ill. The two players coming Edmonton’s way did not establish themselves as major leaguers. Satan? Over 320 NHL goals since the deal.
  • #2: March 17, 1993- Oilers trade L Esa Tikkanen to New York Rangers for C Doug Weight. An absolute killer trade, one that rivals the Pronger deal (the one that got him here) as the best in Oilers’ history. I can’t begin to imagine the Edmonton Oilers in the 90s without Doug Weight.
  • #1: February 27, 2007: Oilers trade L Ryan Smyth to NY Islanders for C Ryan O’Marra, L Robert Nilsson and their 2007 1st rd pick. The pick turned into D Alex Plante and the other two assets proved to be less than inspiring. Smyth was the face of the franchise and this trade more than anything else divided the organization from their fanbase. It is a fracture that remains to this day.
  • D-Man


    You mention the Salo trade getting us a “bona fide top 4 defender”. Who did we get? draft pick? :-))

    Chicago’s first line is incredible but man o man is that a thin roster. I do not think they go 10 deep and the beauty of the Hawks last year was that they were big, fast and DEEP! They ain’t going far in playoffs this year.

    Campbell’s contract impacts their cap so adversely that they have no money for any depth at all. That is a very good lesson to Oiler management that any “overpays” have a huge consequence on a playoffs contending roster

  • D-Man

    Excellent piece here, Lowetide. It’s nice looking back and your list should be bookmarked at this time of year.

    I respectfully disagree with your No. 1 choice, however. I think the Smyth trade was obviously top-12, but I don’t think it was most-significant deadline deal with the franchise, not by a long shot.

    I think the Weight and Marchant deals are Nos. 1 and 2, in that order, simply because they represent, by far, the best deals that involved the trading away of dynasty-era players. I think we can all agree that the Oilers came out on the short end of the stick on the Gretzky, Messier and Fuhr deals, and maybe even the Coffey deal, but the Oilers flat-out won the deals trading away Tik and MacT. The fact that they took place at the pressure of a trade deadline (unlike the other 1980s-superstar-deals) only adds to their remarkability.

    The Weight deal gave them a superstar for the next five or six years or whatever-it-ended-up being. The Marchant deal gave them an excellent two-way player for the same time period and a bit longer. If those two deals don’t happen, there would have been no plucky, underdog, always-chasing-eighth-place Oilers team of the late-1990s and early 2000s – especially not with the way the Oilers were drafting back then.

    In terms of cosmic significance to the franchise, I’d even argue that the Ron Low deal is a far more important one than the Smyth deal. Getting that first-year NHL team into the playoffs for the first time ever was monumentally important in the history of the franchise.

    The Smyth deal? It probably seems big, but I would argue it’s only because it’s so fresh in our minds. But, in terms of overall significance to the franchise, can we really say that the Oilers would be better off with Smyth on the team right now?

    Sweep your emotions aside before you answer that question.

    When you do, you’ll realize that the Smyth deal was big only because it turned into a soap opera – the ultimate example of the dangers of procrastination. Two sides that had almost a year to talk to each other chose to start talking a week or so before the deadline. Then a period of intense (or so we’re told) negotiations ensues, in which both sides end up somewhere in the neighbourhood of $100,000 to $300,000 apart – a normally bridgeable gap that somehow wasn’t closed in time for the deadline.

    And then we have images of Smyth blubbering his way through the Edmonton Airport the next day, supposedly still in shock by the trade (BTW, for that reason alone, his agent, Don Meehan should have been fired. It says here that if your client is still crying the day after a trade that took place because you couldn’t get a contract negotiated in 10 months, you’re not a very good agent – you didn’t do your job).

    All very emotional stuff, yes, but hardly “big” in the bigger picture. The Oilers were still heading downhill. Ryan Smyth, Oiler or not, would not have slowed it any.

    His departure didn’t shift the axis of the Oilers’ orbit at all. I don’t think his presence here would have resulted in any more or fewer free agents signing here and his goal totals would have been on a slow decline (in fact, that probably makes the Satan deal more significant than the Smyth deal).

  • D-Man

    How come the Gretzky trade doesn’t make your top 12 list, Lowetide?? FOR SHAME!! Usually you don’t write any ‘misses’ but this article has a huge miss…

    Granted, that was the darkest of all dark days in Oiler history, but COME ON!! The Ryan Smyth trade?? Ron Chipperfield?? Give me a break!!

    • D-Man

      My apologies… I perhaps should have read the title of your article re: “Deadline” trades…

      I blame one of the many blind side hits I sustained playing minor league hockey…

  • looking at the this list and seeing Jessiman being moved again and remembering his draft position made me remember when you couldn’t turn on a certain radio station in edm without being reminded how old 94 was dealt for essentially Three First Round Picks!!!

    and it turned out great of course.

    • ubermiguel

      Yeah, that was a great move by Lowe and one that was really outside of the normal way he worked.

      Spacek was out there and was being looked at by a few teams and Lowe got the early jump on everyone and got it done and thus gave Spacek all the time he needed to get acclimated with the new club.