Mark Messier accomplished a lot with the Oilers. He ranks third in franchise history with 1034 points and 851 games played, he won four Stanley Cups in the Wayne Gretzky era, and he captained the Oilers to their only non-Gretzky Cup in 1990. But beyond his performance with the team, his trade to the New York Rangers in 1991 began a chain of transactions that led to the Oilers acquiring key players for the next three decades.

With a hat tip to Good Content Boy (and my Large Adult Son) Tyler Yaremchuk for bringing this up yesterday, I’m going to dive into the massive trade tree that began on Oct. 4, 1991, with the Messier trade and now hinges entirely on Ryan Spooner.

The Original Trade: Mark Messier, Jeff Beukeboom, and David Shaw to the New York Rangers for Bernie Nicholls, Steven Rice, and Louie DeBrusk.

Nicholls was a player the Oilers were familiar with. He spent the majority of his career playing with the Los Angeles Kings in the 1980s, putting up a 150-point season in 1988-89 before getting dealt to the Rangers the following season. He would play two seasons in Edmonton before getting dealt to the Devils for Zdeno Ciger and Kevin Todd. Nicholls played a few more solid years in the NHL but just missed out on the Devils winning their first-ever Stanley Cup in 1995.

Ciger would play three-and-a-half years with the Oilers, all of which were during the non-playoff days of the early 1990s. The best years of his career were in Edmonton as Ciger recorded 155 points in 204 games as an Oiler. He was claimed off waivers by the Nashville Predators in 1998 and then returned home to Slovakia.

Kevin Todd didn’t have much of a career in Edmonton. He played 25 games with the Oilers before getting dealt to Chicago for Adam Bennett. Bennett, a former sixth overall pick of the Blackhawks, was a reclamation project for the Oilers. He would only end up playing 48 games for the Oilers. He retired after two seasons spent in the AHL and ECHL.

Louie DeBrusk’s part of the trade tree ends quickly. He had a solid career with the Oilers as a fighter, playing parts of six seasons in Edmonton and scoring 19 goals while racking up 797 penalty minutes. After the 1996-97 season, DeBrusk would sign as a free agent with the Tampa Bay Lightning. He went on to become a colour commentator analyst for the Oilers after his career.

Steven Rice, who was the 20th overall pick of the Rangers in the 1989 entry draft, was the top prospect coming back in the Messier deal. He was dominant for the Oilers’ AHL team in Cape Breton, but never really translated that to success at the NHL level with the club. After two years with the organization, he was dealt in a one-for-one swap to the Hartford Whalers for Bryan Marchment.

Here’s where things start to get a little more interesting. The rugged defender Marchment was around with the Oilers for three-and-a-half seasons before he was packaged up with two of the biggest draft busts in franchise history in a deal with the Tampa Bay Lightning. The Oilers sent Marchment, Steve Kelly, and Jason Bonsignore to Tampa Bay for former first-overall pick Roman Hamrlik and Paul Comrie.

Comrie would only play 15 games with the Oilers and retired at a young age due to injuries. Hamrlik, though, was a stud on Edmonton’s blueline for two-and-a-half seasons, helping the team to a major upset of the Colorado Avalanche in the first round of the 1998 playoffs. After the 1999-00 season, he was shipped off to the Islanders for Eric Brewer, Josh Green, and a draft pick that was used on Brad Winchester.

Brewer, of course, was a highly-touted prospect, drafted fifth-overall by the Islanders in 1997. He was a rock for the Oilers for four seasons and even won an Olympic Gold Medal with Team Canada in Salt Lake City in 2002. After the implementation of the salary cap due to the 2004-05 lockout, the St. Louis Blues needed to shed salary. They dealt Chris Pronger to the Oilers in exchange for Brewer and two prospects, Jeff Woywitka and Doug Lynch. Woywitka, interestingly enough, was a player the Oilers received in the Mike Comrie trade, so he’s technically a part of the tree from here on out.

Pronger helped the Oilers to their amazing run to the Stanley Cup Final in 2006 before requesting a trade shortly after. The Oilers obliged and dealt him to the Anaheim Ducks for Joffrey Lupul, Ladislav Smid, and three draft picks.

We’ll start with Lupul. A local Edmonton product, Lupul was selected by the Mighty Ducks seventh overall in 2002. He appeared to be emerging as an elite young goal scorer in Anaheim after a 28-goal sophomore season and a good showing in the playoffs. He flopped in Edmonton, though, scoring just 16 goals in 81 games. The Oilers flipped him (along with Jason Smith) after just one season to Philadelphia for another former high pick in Joni Pitkanen (and veteran Geoff Sanderson). Lupul, hilariously enough, would end up being involved in another Pronger deal a few years later when the Ducks sent the future Hall of Famer to Philly.

Sanderson played for the Oilers for a year before retiring. Pitkanen didn’t work out in Edmonton. He played here for a season and there are rumours that he spent the whole year living with his mom in a hotel. Regardless, he was sent to Carolina for Erik Cole. Cole played just 63 games in Edmonton before getting sent back to Carolina in a three-way deal that netted the Los Angeles Kings Justin Williams and the Oilers Patrick O’Sullivan. Edmonton also got a second-round pick in that deal, which they would use to acquire Ales Kotalik.

O’Sullivan was a complete disaster in Edmonton. He was fine down the stretch in 2008-09 after being acquired, but, in 2009-10, he scored just 11 goals in 73 games while putting up a whopping -35 rating. He was flipped in the off-season for Jim Vandermeer who played one season in Edmonton before leaving as a free agent. That ends the Lupul part of the tree.

Smid was a mainstay on the Oilers blueline during the decade of darkness. He played 474 games over seven-and-a-half seasons in Edmonton before getting dealt along with Olivier Roy to the Flames for Laurent Brossoit and Roman Horak. Brossoit left this off-season as a free agent and Horak is playing in Sweden. I think Oilers technically still own his NHL rights.

Edmonton got three draft picks in return for Chris Pronger.

One of them was a 2007 first-round pick. They traded Anaheim’s 30th overall pick along with their own second-round pick with the Coyotes to draft Riley Nash. Nash didn’t want to sign in Edmonton and his rights were shipped to the Hurricanes for a second-round pick which was used on Martin Marincin. Marincin bounced back and forth from the Oilers to the AHL and eventually got dealt to the Leafs for Brad Ross and a fourth-round pick. That fourth was dealt to Ottawa for Eric Gryba.

The Oilers also got a second-round pick in 2007. Things get a little weird here. They sent it to the Islanders for Allan Rourke and a third-round pick, which was their own pick that ended up there because the Oilers dealt it along with Marc-Andre Bergeron for Denis Grebeshkov. The Oilers needed that third back so they could sign Dustin Penner to an offer sheet. Rourke played 13 games in Edmonton. Who did the Islanders draft with that second-round pick? Travis Hamonic.

Finally, there was a conditional 2008 first-round pick. If Anaheim went to the Cup Final in 2007, Edmonton got the Ducks’ first-rounder. Anaheim won the Cup, so the Oilers got Anaheim’s 22nd overall pick in 2008. They used that pick to select Jordan Eberle.

I think we all know what went down here. Eberle, an original member of H.O.P.E was a good player for the Oilers who was cast aside during the Connor McDavid era. After the 2017 playoffs in which Eberle didn’t manage to score a goal, he was flipped to the Islanders for Ryan Strome. Strome, an underwhelming return for Eberle, played just a year-and-a-half with the Oilers before getting dealt to the Rangers for Ryan Spooner. And here we are now.

You could also argue that the Pronger picks gave the Oilers the ability to sign restricted free agent Dustin Penner to an offer sheet, which ultimately resulted in them acquiring the draft pick they used on Oscar Klefbom, but that’s a bit of a stretch. They did use that Pronger trade second to get back their third, which got them Penner, who got them Klefbom, but, again, it’s a stretch.

This is just a sad way for it to (possibly) come to an end. Unless Roman Horak makes a surprise return!