Will Holland Continue Oilers Tradition of Draft Week Trades?

NHL Draft week is two weeks away and historically, during the salary cap era, we have seen quite a few big deals starting a few days before the draft, at the draft and even days after. Many of the big trades across the NHL have occurred then, and for Oilers fans, this is when many of your most exciting and head-scratching deals have happened.

Will Oilers General Manager, Ken Holland, keep the trend going?

Here is a list of trades involving the Oiler leading up to the draft, or just after it, and a few deals later in the off-season.

Advertisement - Continue Reading Below


June 26th: Oilers trade Jason Chimera and the 80th pick (Billy Ryan) to Arizona for 52nd pick (Geoff Paukovich) and #112 (Liam Reddox).  Chimera had played 130 games for the Oilers and produced 19-17-36. He never played for the Coyotes, as the 2004/2005 season was cancelled and then he, along with Cale Hulse and Michael Rupp, were traded to Columbus on October 8th, 2005, for Geoff Sanderson and Tim Jackman. Chimera played another 977 NHL games after leaving Edmonton, scored 20 goals three times and finished with 1,107 games played. Reddox played 100 games for the Oilers and scored six goals. Paukovich and Ryan never played. Oilers lost this trade. Head coach Craig MacTavish wasn’t a big believer in Chimera and that is a main reason he was dealt.


These deals didn’t happen around the draft, but were a major reason many younger Oilers fans had the best playoff run of their lives.

August 2nd: The Oilers traded defencemen Eric Brewer, Doug Lynch and Jeff Woywitka for Chris Pronger. And they signed Pronger to a five-year contract. A clear win for GM Kevin Lowe. Pronger was one of the elite D-men in the NHL and was their best player in the 2006 Cup run.

August 3rd: Edmonton traded Mike York and a 4th round pick (Kevin Montgomery) for Mike Peca. Peca wasn’t in great shape when the season began, and struggled much of the regular season playing catchup. But he found his stride in the playoffs and centred Raffi Torres and Fernando Pisani as they became an excellent line in the Cup run. Peca and York only played three seasons after 2006, but Peca’s impact in 2006 is why I give the Oilers the win in this deal.

Advertisement - Continue Reading Below


July 3rd: Less than a month after losing to Carolina in game seven, Pronger asked for a trade and he was traded to Anaheim for Joffrey Lupul, Ladislav Smid a 1st rounder in 2007, a 2nd round pick in 2008 and a conditional first round pick in 2008 if the Ducks won the 2007 Stanley Cup. They won and the Oilers got their first round pick in 2008 and used it to select Jordan Eberle. Usually you lose the trade when you trade the best player, and this deal was no different. Although the Oilers did get a decent return, mainly due to Eberle.


June 21st: Oilers trade the 30th pick (Nick Ross) and 36th pick (Joel Gisbet) to Arizona for the 21st pick and they select Riley Nash. Edmonton ended up with three picks in the top-21, taking Sam Gagner (6th) and Alex Plante (15th). Nash never played for the Oilers. He was dealt to Carolina at the 2010 draft for the 46th pick (Martin Marincin). I included this trade as the 30th pick was from Anaheim in the Pronger trade.

July 1st: Edmonton trades Jason Smith and Joffrey Lupul to Philadelphia for Joni Pitkanen, Geoff Sanderson and the 62nd pick (Cam Abney). Oilers lost this deal as Lupul would play nine more seasons, scoring double digit goals every year, while Pitkanen played one year and Sanderson played 41 games and retired after the season.

July 5th: Not a big trade, but another piece of the Pronger deal. Edmonton traded the 53rd pick (2nd rounder, 2008) they got from the Ducks to the Islanders for Allan Rourke and a third rounder (Kirill Petrov). The Islanders selected Travis Hamonic with that pick. Rourke had been a pro for seven seasons, mainly in the AHL, while playing 42 NHL games over that span, but Lowe gave up a 2nd rounder for him. Unreal. He played 11 games for the Oilers. He didn’t even make the team out of training camp. I’d love to know what the pro scouts were thinking when they recommended him.


June 29th: Edmonton trades Jarret Stoll and Matt Greene to Los Angeles for Lubomir Visnovsky. Visnovsky might have been the most skilled of the three, but he only played 107 games with the Oilers, while Stoll and Greene won two Cups in Los Angeles. Edmonton traded away three of their mid-20s players on the same day (Torres trade below), and it began a downward spiral deeper into the Decade of Darkness.

July 1st: Edmonton trades Raffi Torres to Columbus for Gilbert Brule. While Torres had some suspension issues after this trade, he was still a much more effective NHLer than Brule. Torres admitted to me he needed a trade out of Edmonton. He needed a lifestyle change, and leaving Edmonton, along with the help of his then-girlfriend, now wife, he got his life in order off the ice.

Advertisement - Continue Reading Below

July 1st: Edmonton trades Pitkanen to Carolina for Erik Cole. Pitkanen was in Edmonton for one season. Cole didn’t even last a full season as he was part of a three-way deal that saw Cole go to Carolina, Justin Williams go to Los Angeles and Edmonton acquire Patrick O’Sullivan and a 2nd round pick. They then traded that 2nd round pick to Buffalo for Ales Kotalik, as the Oilers were in a playoff race. They missed the playoffs by three points.

From July 1st 2007 to March 4th, 2009 the Oilers went from having Smith and Lupul to having O’Sullivan. It wasn’t O’Sullivan’s fault, but the constant trading of the players one year after they acquired wasn’t wise. There was no continuity on the team.

2009…Steve Tambellini GM

I vividly remember sitting in the media riser on the draft floor in Montreal when this trade was announced. This wasn’t a big trade, but it was another loss.

June 27th: Oilers trade Kyle Brodziak and the 161st pick (6th round, Darcy Kuemper) to Minnesota for the 99th pick (4th, Kyle Bigos) and 132nd pick (Olivier Roy). Brodziak had developed in the organization, playing three seasons in the AHL and then two with the Oilers where he 14 and 11 goals, while being a strong penalty killer. They felt Marc-Andre Pouliot was a better player. The trade was bad, but it got much worse when the Wild hit on their pick and the Oilers missed on both of theirs.


Some small deals around draft week.

June 24th: Oilers trade 6th round pick (151st, Mirko Hoefflin) to Chicago for Colin Fraser.
June 26th: Oilers trade Nash to Carolina for the 46th pick and select Marincin.
June 30th: Oilers trade O’Sullivan to Arizona for Jim Vandemeer.

Advertisement - Continue Reading Below

So the Smith/Lupul trade tree ended at Vandemeer. In three years it went from the Oilers having Smith and Lupul to having Vandemeer, and then nothing. He played one season with the Oilers and then signed as a UFA in San Jose.


June 26th: Oilers send Fraser to Los Angeles for Ryan Smyth. One of the most popular Oilers came home. Smyth was the better player, but he had a much higher salary. He played three seasons with the Oilers before retiring. Fraser won a cup with the 2012 Kings. Quite a career for him winning one in Chicago as well.

July 1st: Oilers trade Kurtis Foster to Anaheim for Andy Sutton.

July 5th: Oilers trade Andrew Cogliano to Anaheim for a 2nd round pick (Marc-Olivier Roy) in 2013. Cogliano had the 6th most points (35) on the Oilers during the 2010/2011 season. Jordan Eberle led the team with 43 in his rookie season. Cogliano was an RFA and coming off a one-year deal that paid him $1million and he’d filed for arbitration and his arbitration date was July 21st. He was moved for a 2nd round pick that wouldn’t be picked for two seasons. Edmonton had just added Taylor Hall, Eberle and Ryan Nugent-Hopkins was drafted a few weeks earlier. They traded Cogliano away to make room for RNH, but didn’t get an NHL player in return. Not the best way to insulate your young players, by weakening the cast around them. Even worse, the draft pick wasn’t until 2013, which means at best that player was going to play in 2016. Ugh.

Cogliano signed a three-year deal with the Ducks ($2.39m AAV) on July 19th. They moved him to the wing, and he played 7 1/2 seasons with the Ducks and only missed two games. Both due to a weak suspension by the NHL.

Advertisement - Continue Reading Below


No draft week or off-season trades.

2013…Craig MacTavish GM

July 4th: Oilers send Shawn Horcoff to Dallas for Philip Larsen and a 2016 7th round pick. Horcoff had two years remaining on his contract ($5.5m AAV) and this was a combination of a salary dump and moving him to a competitive team.


July 10th: Oilers trade Magnus Paajarvi and a 2014 2nd round pick (Ivan Barbashev) to St. Louis for David Perron. A solid trade for the Oilers as Perron scored 28 goals and 57 points, third most on the team, before he was dealt to Pittsburgh on January 2nd, 2015 for Rob Klinkhammer and a 2015 1st round pick. Perron had one more year on his contract, so he didn’t have to be traded. He’d struggled with only five goals and 19 points in 38 games, but trading away another proven NHL player for draft picks is always a big risk. On January 2nd the trade looked okay, but six months later it became a disaster.

2015…Peter Chiarelli GM

Brace yourself Oilersnation. This starts the trend of some horrific draft week/off-season trades.

Peter Chiarelli was hired on April 24th, six days after Edmonton won the Connor McDavid draft lottery. His first trade was his worst.

Advertisement - Continue Reading Below

June 26th: Edmonton’s trades the 16th and 33rd picks in the 2015 draft to the New York Islanders for Griffin Reinhart. Reinhart had just finished his first pro season. He played 59 games in the AHL and eight in the NHL. He wasn’t even in the top pairing in the AHL, but the Oilers felt he was worth two high picks. A crippling trade for the Oilers. Reinhart played 29 regular season games and one playoff game in the next two seasons, before Vegas claimed him in the expansion draft. The Islanders selected Matt Barzal at 16 and dealt the 33rd pick along with the 72nd pick to Florida for the 28th pick. They drafted Anthony Beauvillier. Barzal has scored 207 points in his first three NHL seasons, while Beauvillier has emerged as a 2nd line winger in New York.

This trade was terrible the moment it was made. I felt Reinhart was likely a third pairing defender, turns out that was even too high. This trade is the worst of the Chiarelli era, because the Oilers got basically nothing for those two high draft picks.

June 27th: Oilers acquire Cam Talbot and a 2015 7th rounder (Ziyat Paigan) from the Rangers for three picks in 2015: A 2nd (Jonas Siegenthaler), a 3rd ( Sergei Zborovskiy) and a 7th (Adam Huska). Big win for the Oilers as Talbot became their starting goalie and helped them make the playoffs in 2017.


Bob McKenzie tweeted the now infamous words, “Trade is one for one.”

June 29th: Oilers trade Taylor Hall to New Jersey for Adam Larsson. Hall was clearly the better player. Chiarelli even admitted it. “That’s a fair comment, if you look at just what they’ve accomplished so far in the league. Larsson doesn’t have the same pedigree yet, but I believe in him a lot. He moves the puck quickly. He’s very smart,” he said when asked about the trade.

Advertisement - Continue Reading Below

Larsson is a solid NHL player, and it was not his fault who he was traded for. But this was another horrific trade by Chiarelli, and I wrote it at the time. It became worse a few days later when the Oilers signed Milan Lucic for seven years. Clearly they had the Lucic signing done, when they made the Hall trade. They’d have been much better off keeping Hall and signing Jason Demers as a UFA defender. This trade wasn’t nearly as bad as the Reinhart deal, because Larsson is a solid top-four defender. He just isn’t as impactful as Hall.


June 22nd: Oilers trade Jordan Eberle to the Islanders for Ryan Strome. The deal was made to supposedly made to create cap space, but then Edmonton didn’t add anyone else. Eberle was the better scorer and more proven NHL player. I felt the deal was made because Eberle didn’t have a good playoffs in 2017. I expect fans to overreact to a bad playoffs, but not an experienced GM. Yes, Eberle struggled in his first playoffs, but so did Lucic and Ryan Nugent-Hopkins that year. Eberle has 25 points in 30 playoff games the past two seasons with the Islanders. Most scorers figure out how to produce in the playoffs.

This deal looks much worse now, due to Chiarelli trading Strome away 17 months later for Ryan Spooner and downgrading in skill even more.


No draft week trades.

2019…Ken Holland GM

July 19th: Oilers trade Milan Lucic to Calgary for James Neal and a third-round pick. Oilers retain $750,000 of Lucic’s salary. The pick will likely be in 2021. Edmonton has the option to trade this year’s pick, but it sounds like they keep this year’s pick. Makes sense. It is the 14th pick in the third round, and Edmonton is expecting to be better next season, thus making it a later pick next season. Neal scored 19-12-31 in 55 games while Lucic had 8-12-20 in 68 games. Despite some trying to act as though powerplay points don’t count, Neal was much more productive in year one. Each player has three years remaining on their deal, so it is too early to say who benefitted more from the trade, but after year one it was Edmonton.

Advertisement - Continue Reading Below

2020…What Will Happen?

I expect Holland to make a move in the coming weeks, but I’m not sure it will be a major move. Historically, Holland has been patient. I don’t expect him to overreact to the Oilers qualifying round loss to Chicago. They made improvements in the second half of the season, mainly cutting down their goals against, but their 5×5 GA was still only 19th best at 2.06/game. Their 5×5 GA hasn’t improved at all over the past three seasons, and it is why I’d change the makeup of the blueline.

I sense Holland would like to change his defence, but unlike his predecessor, I doubt he panics and makes a desperate trade.

Adam Larsson seems the most likely trade chip, but if you move him Edmonton has to get a right shot defender in return. Kris Russell is a solid NHL defender. His cap hit is the bigger issue. Russell has a 15-team no-trade list, but that means there are 15 teams he could be traded to. Eric Stall didn’t have Buffalo on his list, because he didn’t think they’d be interested, so trading Russell, while challenging, is far from impossible. Edmonton likes his ability to play both sides, although Caleb Jones can play both as well and he’s much cheaper and a better puck mover.

I don’t envision Holland making a Chiarelli-like move and downgrading the skill of his team. I also don’t see him landing a superstar like Lowe did with Pronger, and then having to trade him away the following summer. But many of the NHL’s biggest deals occur around the draft.

In the past few seasons we have seen the likes of PK Subban (twice), Shea Weber, Hall, Tyson Barrie, Phil Kessel (twice), Nazem Kadri, Jacob Trouba, Ryan O’Reilly and Dougie Hamilton dealt in the days around the NHL draft. We will see a few more in the coming weeks, and there will likely be some unexpected names moved.

Edmonton has two superstars. It would be great to add another elite star, but Holland will be more focused on trying to improve the supporting cast around them. History tells us his best chance to do it will occur in the next 20 days.

Recently by Jason Gregor: