The Mark Messier Transaction Tree officially comes to an end with Oscar Klefbom’s contract expiring

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 with the team during the 1980s, and he captained the Oilers to their first and only non-Wayne Gretzky Cup in 1990. But beyond Messier’s performance with the team, his trade to the New York Rangers in 1991 began a chain of moves that led to the Oilers acquiring some key players for the next three decades.

The transaction tree that started with the Oilers sending Messier to the New York Rangers in exchange for Bernie Nicholls, Louie DeBrusk, and Steve Rice will officially come to an end on July 1 when Oscar Klefbom’s contract expires.

So, how did the Messier trade lead to the Oilers acquiring the likes of Roman Hamrlik, Chris Pronger, and Klefbom? Let’s start from the beginning…

This part of the transaction tree ended quickly.

Nicholls was the best player coming back to Edmonton in the deal and he was a player Oilers fans from this era would know well because of his time in Los Angeles. Nicholls put up a 70-goal, 150-point season in 1988-89 alongside Wayne Gretzky in his first season after being traded to the Kings and posted 758 points with the Kings throughout the 80s.

He would spend a year and a half with the Oilers, scoring 89 points in 95 games before getting traded to the New Jersey Devils for Zdeno Ciger and Kevin Todd. While Todd never became anything, Ciger was a solid Oiler for parts of four seasons before returning home to Slovakia in 1996.

DeBrusk’s role in the chain is fairly short, too.

He would play six seasons in Edmonton, scoring 19 goals and 31 points while racking up a whopping 797 penalty minutes before leaving the team in 1998 to sign as a free agent with the Tampa Bay Lightning.

DeBrusk, of course, is still involved with the Oilers as a colour commentator on the team’s broadcasts with Sportsnet.

Buckle up. Here’s where things start to get interesting.

Steven Rice, a former 20th overall pick of the Rangers in 1989, was the top prospect coming back to Edmonton in the Messier deal. Rice was dominant for the Oilers’ AHL affiliate in Cape Breton, but he could never translate to the NHL. After two years with the organization, the Oilers would send him to the Harford Whalers in a one-for-one swap for defender Bryan Marchment.

Marchment spent three-and-a-half seasons with the Oilers before getting packaged with infamous draft busts Jason Bonsignore and Steve Kelly in a deal with the Lightning for former first-overall pick Roman Hamrlik and Paul Comrie.

Comrie only played a few games with the Oilers and retired early due to injuries, but Hamrlik was a stud on Edmonton’s blueline for two-and-a-half years. After the 1999-00 season, Hamrlik was shipped to the New York Islanders in exchange for Eric Brewer, Josh Green, and a draft pick the team would use on Brad Winchester.

Green and Winchester don’t matter much, but Brewer plays a key role. The former fifth-overall pick was a rock for the Oilers on the blueline for a few years and he was the youngest member of the 2002 Gold Medal-winning 2002 Canadian Olympic Team in Salt Lake City. After the lockout, Brewer was dealt along with Jeff Woywitka and Doug Lynch to the St. Louis Blues for Chris Pronger.

Pronger’s time in Edmonton was short-lived, but it was incredible. He was a dominant force on the Oilers’ blueline, logging 27:59 per game and putting up 56 points in the regular season. In the playoffs, Pronger reached a new level, logging 30:57 per game and posting 21 points in 24 games. How he didn’t win the Conn Smythe Trophy that year is beyond me.

Pronger, of course, would demand a trade following the playoffs. He would end up getting shipped to Anaheim for Joffrey Lupul, Ladislav Smid, and three draft picks. The chain gets really, really wild here.

We’ll start with Lupul. The local Edmonton product was coming off a 28-goal breakout season in Anaheim, but he was a flop with the Oilers, scoring just 16 goals in 2006-07. He would get shipped to Philadelphia in the off-season for Joni Pitkanen, who would get shipped to Carolina for Erik Cole, who would get shipped to Carolina via Los Angeles in a three-team deal for Patrick O’Sullivan, who would get shipped to Phoenix for Jim Vandermeer. Vandermeer left as a free agent, ending the Lupul chain. Ironically, Lupul would again get traded in a Pronger deal a few years later when the Ducks sent the future Hall of Fame defender to Philadelphia.

Next, we have Smid, who was a solid contributor to the Oilers’ blueline during their dark years. Smid would spend parts of eight seasons with the Oilers before getting shipped to the Flames for Laurent Brossoit and Roman Horak. Brossoit left the team as a free agent and Horak has been playing in Europe since the 2014-15 season.

Next up, we have the draft picks from the Pronger trade.

Edmonton dealt Anaheim’s 30th overall pick at the 2007 draft plus their own second-round pick to Phoenix to move up to No. 21 overall to draft Riley Nash. Nash didn’t want to sign in Edmonton and was dealt to Carolina for a second-round pick in 2010, which the Oilers used in Martin Marincin. The Oilers would later deal Marincin to Toronto for Brad Ross, who never played for the team, and a fourth-round pick they would later flip to Ottawa for Eric Gryba, which ends this part of the chain.

Since the Ducks won the Stanley Cup in 2007, the Oilers received Anaheim’s top pick in the 2008 draft as well. They would use that pick on Jordan Eberle, while the Ducks, with Edmonton’s first-round pick as compensation for Penner, traded down with Buffalo to draft Jake Gardiner and Viktor Tikhonov. Buffalo would use Edmonton’s pick on Tyler Myers. Anaheim used the second-round pick from Edmonton to draft Justin Schultz, who would end up signing with the Oilers rather than the Ducks due to the NCAA draft pick loophole.

Eberle was a key member of H.O.P.E during Edmonton’s Oil Change. He would play seven seasons here, recording 382 points. After Edmonton’s 2017 playoff run, Eberle was shipped to the Islanders in exchange for Ryan Strome. A few months into his second season with the Oilers, Strome was sent to the Rangers for Ryan Spooner, who was later flipped to the Canucks for Sam Gagner.

Gagner’s second go-around with the Oilers lasted until the following season when he was moved to Detroit as part of the package that netted Edmonton Andreas Athanasiou. He scored one goal and one assist with the Oilers in games before the season was paused due to COVID-19. During the off-season, the Oilers opted not to issue Athanasiou a qualifying offer and he left the team as an unrestricted free agent, ending Eberle’s part of the chain.

After Athanasiou left, the Oilers had just one connection to Messier remaining — Oscar Klefbom.

The Oilers dealt Anaheim’s second-round pick in the 2007 draft to the Islanders for Allan Rourke and Edmonton’s own third-round pick that had been sent to New York a few months earlier in exchange for Denis Grebeshkov. This deal was made by Kevin Lowe so that he could have Edmonton’s own first three picks in the 2008 draft in order to sign Dustin Penner to an offer sheet.

Penner played parts of four seasons with the Oilers and scored 93 goals and 93 assists over 304 games. He was traded ahead of the 2011 trade deadline to L.A. for prospect Colten Teubert and their first-round pick. Teubert only played a handful of games in the NHL but the Oilers struck gold with that draft pick by selecting Klefbom at No. 19 overall.

Klefbom made his debut with the Oilers in 2013-14 and established himself as a top-four defender very quickly. The Oilers inked him to a seven-year contract extension in the fall of 2015 after Klefbom had played just 77 games in the NHL. Klefbom was Edmonton’s top defender for the next five seasons, as he put up 133 points over 301 games and averaged 23:23 per night.

Unfortunately, Klefbom’s promising career was cut short because of a chronic shoulder injury. He was shut down before the end of the 2017-18 season in order to have shoulder surgery and the issues resurfaced during the 2019-20 season. Klefbom wound up going on the Long-Term Injured Reserve for the final three years of his contract and the last game he played in the NHL came in front of an empty arena during Edmonton’s bubble playoff series with the Chicago Blackhawks.

This entire transaction tree paints an interesting picture of how the Oilers managed to constantly retool their team on the fly as they struggled through the realities of being a small-market team in the pre-salary cap era.

The Oilers selected Messier with the No. 48 overall pick in 1979, their first-ever draft after merging into the NHL from the WHA. He made his debut in their inaugural NHL season and is one of only a few players who was around for all five of the team’s Stanley Cups.

As with Wayne Gretzky and the rest of The Boys on the Bus from the 1980s, it’s a shame that Messier didn’t spend his entire career in Edmonton. But that said, Messier continued to have an impact on the organization well after he left, as savvy moves by Glen Sather and Kevin Lowe helped the Oilers return to being competitive after their early-1990s lull.