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Monday Mailbag – What are the best and worst deadline day trades by the Edmonton Oilers?

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Photo credit:Tom Kostiuk
baggedmilk
1 month ago
Happy long weekend, Internet friends, and welcome to another brand new Mailbag to help get your week started and keep you updated on all things NHL. This week, we’re discussing the best and worst Oilers moves at the trade deadline, defensive depth, the drawbacks of going all in, and more. If you’ve got a question you’d like to ask, email it to me at baggedmilk@oilersnation.com or hit me up on Twitter at @jsbmbaggedmilk , and I’ll get to you as soon as we can.
1) Kev asks – We’re approaching the NHL trade deadline, and I’m wondering what everyone thinks are the best and worst historical Oilers trades leading up to deadline day?
Tyler Yaremchuk:
The one that stands out as bad was the Jarred Smithson deal because there was excitement that the Oilers would do something to boost their playoff chances and they did… that. Also, the Mike Green deal is hilarious because he played like two games.
Jason Gregor:
The best would have to be Kent Nilsson in 1987, as the Oilers won the Cup.
Next best would in 1988 when Oilers dealt Andy Moog to Boston for Geoff Courtnall and Bill Ranford. Courtnall was a decent contributor for the 1988 Cup win, while Ranford didn’t play in playoffs that year, but he won the Conn Smyth for EDM in 1990. Arguably two Cups came from this deal.
The 2006 Dwayne Roloson trade for a 1st (Trevor Lewis) would be #3 based on playoff success. Got the Oilers a great run to Cup Final. However, acquiring Doug Weight for Esa Tikkanen in 1993 had much more long term success than the Roloson deal.
Honorary mention to the 1999 trade deadline. Sather made two great trades.
  1. Acquired Jason Smith from Toronto for a 4th and 5th round pick.
  2. Acquired Tommy Salo from Islanders for Mats Lindgren and an 8th rounder.
Worst deals…
  1.  The 2007 deadline when they traded Ryan Smyth for Robert Nilsson, Ryan O’Marra and a 1st (Alex Plante).
  2. 1997 when they dealt Miroslav Satan to Buffalo for Barrie Moore and Craig Miller.
    3. Moving a young Martin Rucinsky to Quebec for Ron Tugnutt and Brad Zavisha in 1992.
  3. In 2013, even though it cost very little, a 4throunder (Matt Buckles), the Oilers acquiring Jerrid Smithson to help them down the stretch was symbolic of the Decade of Darkness.
Zach Laing:
In aggregate, the 2005-06 trades were the best. Honourable mentions: picking up Willy Lindstrom in 1983, acquiring Kent Nilsson in 1987,  trading Paul Coffey to the Penguins for Craig Simpson and others, and both Bill Guerin deals worked out great.
Trading Ryan Smyth away in 2007 was the worst leading up to the deadline.
Baggedmilk:
In hindsight, the Andreas Athanasiou trade went about as badly as you could have imagined. Not great from start to finish. Derrick Brassard was just a dude that existed when Holland brought him in for a late pick. And, of course, how could I not talk about hating the Ryan Smyth trade. It’s the reason this website exists.
On the flip side, my favourite deadline deal might be the one to bring in Sergei Samsonov. I always loved that guy and I was so excited when the Oilers got him at the deadline.
Nov 20, 2023; Sunrise, Florida, USA; Florida Panthers center Carter Verhaeghe (23) battles Edmonton Oilers defenseman Philip Broberg (86) for the puck during the second period at Amerant Bank Arena. Mandatory Credit: Jasen Vinlove-USA TODAY Sports
2) Sara asks – How concerned are you with the Oilers’ defensive depth? It seems to me that the team is only one injury away from Philip Broberg being recalled and two injuries away from having an unknown commodity on the blue line. Am I looking too far into this or is the depth chart a little shallow on the back end?
Tyler Yaremchuk:
I’m worried about both their forward and defensive depth honestly. I would be fine if Broberg gets in for a stretch but they’ll need eight defensemen to get through a long playoff run. They need one more. Their fourth line also is not good enough so they need to fix that.
Jason Gregor: 
Valid concern and why I think it is a guarantee they will add a veteran depth defender at the deadline.
Zach Laing: 
I’m not content with the depth at either position. The Oilers have two players on their fourth line in Mattias Janmark and Connor Brown who are boat anchors, while their third-line can’t score a goal to save their lives, no matter how much they dominate the pace of play. The Oilers need to add both up front and on the blue line.
Baggedmilk:
Injuries are always a concern, and the Oilers have had some really good luck so far this season. We just have to hope it continues, I suppose. I’d like to see Holland add a top-six winger and a RHD, if I’m being greedy.
Photoshop: Tom Kostiuk
3) Oilers fan in Van asks – Does ‘going all in’ even make sense? Last year, the Bruins made trades at the deadline and got bumped in the first round. The Leafs made a bunch of trades last year and only won five games. Why does everyone think going all in at the trade deadline is going to magically pay off?
Tyler Yaremchuk:
I view going all-in as just being willing to spend whatever assets necessary to fix holes on your roster. Boston maybe went a little overboard but the Oilers need one or two impact forwards and a depth defenseman and they shouldn’t avoid making those adds because prices are too high. If it cost the first-round pick, then so be it.
Jason Gregor:
I don’t think going all in pays off. I think smart, calculated moves that bring a player with term make more sense. Like Ekholm. I’d have no issue giving up the 1st round pick for a player who is signed to the end of 2025. But giving up a 1st for a pure rental, isn’t the best plan for me.
Zach Laing:
Only one team wins the Stanley Cup every year, and 31 finish the year disappointed. Among the 16 teams who make it into the playoffs, numerous teams will buy, and a few will go all-in.”
If you’re a team like the Vancouver Canucks, going all-in makes sense because, for as good as they’ve been this year, they have had some pretty notable holes. The Oilers don’t have as many holes to fill, and moves to add depth is what they’re looking for.
Baggedmilk:
You don’t have to trade for everyone that’s available, but I do think there are some holes that need plugging. Top six winger, 3C, defensive depth… they also stick out to me.
The Coachella Valley Firebirds play the Bakersfield Condors at Acrisure Arena in Palm Desert, Calif., Dec. 23, 2023.
4) Dakota asks – We’ve seen Vancouver and Calgary both move their AHL teams back to Canada. Will/Should the Oilers follow suit?
Tyler Yaremchuk:
I would like that. There’s an advantage to having your AHL club be a short drive away. It makes things like emergency recalls easier to do. I would love to see the Oilers AHL club be closer to Edmonton.
Jason Gregor:
I doubt the Oilers do. The AHL team wouldn’t draw very well here, plus in Bakersfield the travel is much better, less costly, than having the team here. The main benefit to having the team in Edmonton, is if you get in injury trouble, or if you want to send a young player up and down easily. I was told they have zero plans to move team to Edmonton.
Zach Laing:
It makes a ton of sense to have your AHL team close to your NHL team, and with Calgary and Vancouver doing so, I wonder how much it would open the AHL up to letting it happen again.. However, last February the Condors signed a lease extension through 2028, with an option for three more years, so it wouldn’t be until then, at the earliest, a move to Alberta would happen.
Baggedmilk:
That would be fun if the Condors are close. I’ve never been able to watch them live, and that would be a nice perk over and above having the farm team in closer proximity to the parent club.
5) Ed M. asks – By Monday, this question may have been beaten to death, but what about five games for Rielly? But as an aside question on this. Was there any reason for the Leaves to feel retribution was needed because a guy shot the puck hard into an empty net? It seems this happens almost every game in the NBA. Some guy gets a free run at the basket, and instead of politely depositing the ball in the basket, a hoop-breaking slama jama is done and it’s heralded as a great play. Why don’t we see similar retribution in the NBA?
Tyler Yaremchuk:
I loved the play from Greig. I liked that Reilly did something about it, he just shouldn’t have cross-checked him in the face. Rivalries are fun!
Jason Gregor:
Greig knew taking the clapper would illicit a response and I had no issue with him taking the shot, or Rielly coming over. Rielly’s error was that he didn’t crosscheck him in the shoulder. Do that and nothing happens.  The NBA also has flopping every game, and they have flagrant fouls when guys stop guys from dunking. I’ve seen many guys go up for a dunk or layup and have opposing player take him out. To say it doesn’t happen isn’t accurate.
Most NBA games end with guys just dribbling ball to kill the clock, just like most EN goals the player slides it in, or shoots from his own end. The NHL and NBA have guys who react when they feel the opposition is showboating or trying to show them up. I’m fine with all of it. We need more emotion in the game.
I’d much rather see Rielly go after a guy like that, than the hits from behind we see too frequently that go unpunished.
Zach Laing:
Five games is fine. You can’t cross-check somebody in the head.
Baggedmilk:
More WWE wrestling in hockey, please. I don’t mean the actual wrestling, but rather the villain storylines. The league could do a lot with a few more spicy affairs.

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