It’s not very often a team trades not just one of the best players in franchise history, but one of the best players in the sport’s history, and eventually comes out the winner.
Before starting the 1991-92 season, the Edmonton Oilers traded Mark Messier to the New York Rangers. As you know, Messier won his sixth Stanley Cup with the Rangers in 1994 and finished second in all-time scoring before being passed by Jaromír Jágr in 2016.
In return, the Oilers received Louie DeBrusk, Bernie Nicholls, Steven Rice, and David Shaw, kicking off an incredibly beneficial trade tree for the Oilers over the next three decades.

The original trade and its branches

Louie DeBrusk played six seasons with the Oilers from the 1991-92 season until the 1996-97 season, scoring 19 goals and 31 points in 228 games and 797 penalty minutes. He signed with the Tampa Bay Lightning before the 1997-98 season and played for the Phoenix Coyotes and Chicago Blackhawks before hanging up his skates at the end of the 2003-04 season. DeBrusk serves as the Oilers’ colour commentator.
David Shaw played three 12 games for the Oilers, eventually being traded to the Minnesota North Stars for Brian Glynn. Glynn played parts of two seasons for the Oilers, scoring six goals and 24 points in 89 games before the Oilers traded him to the Ottawa Senators for the eighth-round pick in the 1994 draft. With that pick, the Oilers selected Rob Quinn, who never played a National Hockey League game and tragically passed away in a car accident in 2008.
Bernie Nicholls spent parts of two seasons with the Oilers, scoring 28 goals and 89 points in 95 games before being traded to the New Jersey Devils for Zdeno Cíger and Kevin Todd. Cíger played four seasons with the Oilers, scoring 64 goals and 155 points in 204 games, leaving for Czechia following the 1995-96 season.
As for Todd, he played a season with the Oilers, scoring four goals and 13 points in 25 games before being traded to the Chicago Blackhawks for Adam Bennett before the beginning of the 1993-94 season. Bennet played for the Oilers in 1993-94, scoring three goals and nine points in 48 games, and never played another NHL game after this season.

The meat and the potatoes

Of the four players the Oilers received in the Mark Messier trade, only one kept this trade tree alive heading into the new millennium. Steven Rice played parts of three seasons for the Oilers, scoring 19 goals and 39 points in 94 games. At the end of the 1993-94 season, the Hartford Whalers offer sheeted him, trading Bryan Marchment in return.
Marchment spent parts of four seasons with the Oilers, scoring seven goals and 44 points in 216 games. Late in 1997, he was traded to the Tampa Bay Lightning, along with Jason Bonsignore and Steve Kelly, for Roman Hamrlík and the rights to Paul Comrie.
Starting with Comrie, he only played 15 games with the Oilers in 1999-2000, scoring a goals and three points in 15 games. However, Hamrlík had a much bigger impact for the Oilers, playing 196 games for the Albertan team, scoring 22 goals and 103 points as a defenceman.
During the 2000 off-season, Hamrlík was traded to the New York Islanders for Eric Brewer, Josh Green, and a 2000 second-round pick that turned out to be Brad Winchester.
Starting with Winchester, he played 74 games with the Oilers from 2005-06 until 2006-07 before leaving the team as an unrestricted free agent. Green played parts of three seasons with the Oilers, two initially, playing 81 games from 2001-02 until midway through the 2002-03 season where he scored 10 goals and 17 points. 
Green was traded to the New York Rangers in Dec. 2002 for a conditional pick. It doesn’t seem that the pick transferred to the Oilers, but Green played his final National Hockey League season with the Oilers in 2011-12, scoring a goal and two points in seven games.

The Chris Pronger era and fallout

The other player the Oilers received in the Hamrlík trade was Eric Brewer, who had an impact on the ice and as a trade piece for the team. Playing four seasons with the Oilers, the defenceman scored 29 goals and 100 points in 315 games.
On Aug. 2, 2005, the Oilers traded Brewer, Doug Lynch, and Jeff Woywitka to the St. Louis Blues in exchange for star defenceman Chris Pronger. As for Brewer, he had a successful end to his career, scoring 43 goals and 158 points in 605 games with the Blue, Tampa Bay Lightning, Anaheim Ducks, and the Toronto Maple Leafs.
Pronger logged significant minutes for the Oilers in 2005-06, scoring 12 goals and 56 points in 80 games. The Oilers made the eighth-seed in the 2006 postseason and went on a miraculous run to Game 7 of the Stanley Cup Finals. In the postseason, Pronger scored five goals and 21 points in 24 games while playing over 30 minutes a night.
However, Pronger’s tenure with the Oilers didn’t last long though, as the defenceman was traded to the Anaheim Ducks shortly after the Game 7 loss for Joffrey Lupul, Ladislav Šmíd, a 2007 first-round pick (Nick Ross), a 2008 second-round pick (Travis Hamonic) and a conditional 2008 first-round pick (Jordan Eberle).
Lupul played only a season with the Oilers, scoring 16 goals and 28 points in  81 games as the Oilers failed to make the postseason. In the off-season, he was traded to the Philadelphia Flyers for Joni Pitkänen, Geoff Sanderson, and a 2009 third-round pick, Cameron Abney.
Like Lupul, Pitkänen only played a season for the Oilers, scoring eight goals and 26 points in 63 games before being traded exactly a year later to the Carolina Hurricanes for Erik Cole. The winger played 63 games with the Oilers, scoring 16 goals and 27 points before being traded back to the Hurricanes (along with a 2009 fifth-round pick) for Patrick O’Sullivan and a 2009 second-round pick that turned out to be Jesse Blacker.
O’Sullivan played parts of two seasons with the Oilers, scoring 13 goals and 40 points in 92 games before the Oilers traded him to the Phoenix Coyotes for Jim Vandermeer. The defenceman played a season with the Oilers, scoring two goals and 14 points in 62 games, assisting on Jordan Eberle’s first career goal. More on the winger later, though.
Moving to the Šmíd part of the Pronger trade, the Czech defenceman played parts of eight seasons with the Oilers, scoring 11 goals and 65 points in 474 games during the decade of darkness. Early in the 2013-14 season, he was traded to the Calgary Flames for Laurent Brossoit and Roman Horák.
Brossoit only played 28 games for the Oilers, posting an .897 save percentage and a 2.98 goals-against average in the four seasons he spent with the team. After leaving the Oilers as a free agent, he has a .914 save percentage and a 2.56 goals-against average in 112 games playing for the Winnipeg Jets and Vegas Golden Knights.
Horák, on the other hand, played two games with the Oilers in 2013-14 and has played in Europe since 2014-15. He currently played for Sparta Praha in his home nation of Czechia.
Anaheim’s 2007 first-round pick was traded with the Oilers’ second-round pick to move up to the 21st overall pick to select Riley Nash.  However, he was traded to Carolina shortly after for a second-round pick in the 2010 draft to select Martin Marinčin. Overall, the defenceman scored a goal and 11 points in two seasons with the Oilers.
At the 2015 draft, Marinčin was traded for a 2015 fourth-round pick, along with Brad Ross, from the Toronto Maple Leafs. That pick was flipped with Travis Ewanyk to the Ottawa Senators for Eric Gryba, who played three seasons with the Oilers, scoring three goals and 14 points in 114 games. Moreover, that pick turned out to be defenceman Christian Wolanin, who has played 86 NHL games with six goals and 23 points, most recently playing with Vancouver Canucks in 2022-23.
The 2008 second-round pick the Oilers got in return for Pronger was the 53rd-overall pick. Edmonton traded it to the New York Islanders to acquire Allan Rourke and a 2008 third-round pick that turned out to be Kirill Petrov. Rourke played 13 games for the Oilers with five penalty minutes and later signed with a European team. 
The Petrov pick is interesting because it jumped multiple teams. Originally belonging to the Oilers, it was traded to the Islanders for Denis Grebeshkov and was traded back to the Oilers for Anaheim’s second-round pick in 2008. The Oilers then used it in an offer sheet for Dustin Penner, who played for the Ducks, before Anaheim moved it back to the Islanders.
Petrov never played a game in the National Hockey League, playing his entire career in the Kontinental Hockey League, save for 13 games in the American Hockey League. However, the 2008 second-round pick was used by the Islanders to select Travis Hamonic, who has gone on to have a pretty solid career in the NHL.

The modern era

Šmíd was a useful player for the Oilers, but Jordan Eberle was by far the best player the Oilers received in the Chris Pronger trade, and it’s only because Pronger won the Stanley Cup with the Ducks in 2007.
Eberle was selected 22nd overall by the Oilers in 2008 and spent seven seasons with the team, scoring 165 goals and 382 points in 507 games. He was traded to the New York Islanders for Ryan Strome, who played parts of two seasons with the Oilers, scoring 14 goals and 36 points in 100 games. Strome was then traded to the New York Rangers for Ryan Spooner, who played 25 games with the Oilers, scoring two goals and three points, before the Oilers shipped him to the Vancouver Canucks for Sam Gagner.
In Gagner’s second stint with the Oilers, he scored 10 goals and 22 points in 61 games before the Oilers traded him, along with a 2020 and 2021 second-round pick, to the Detroit Red Wings for Andreas Athanasiou and Ryan Kuffner at the 2020 trade deadline.
Athanasiou played nine regular season games with Edmonton, scoring a goal and two points in nine games while being held pointless in four postseason games. He departed the Oilers following the 2019-20 season, while Kuffner never played for the Oilers.
Early in the trade tree, we start with an offer sheet, and the last player we’ll look at comes following an offer sheet. The Oilers moved a piece from the Pronger trade to regain their own third-round pick in the 2008 draft. A few weeks after that trade, the Oilers gave Dustin Penner an offer sheet, losing their first-round, second-round, and third-round picks in the 2008 draft.
Penner played 304 games with the Oilers in parts of four seasons, scoring 93 and 186 points in 304 games. The three players the Ducks received were Jake Gardiner, Justin Schultz, and Viktor Tikhonov. Funnily enough, Schultz was playing in the NCAA and decided to sign with the Oilers instead of the Ducks when he turned professional.
As for Penner, he was traded back to the Los Angeles Metropolitan area to the Los Angeles Kings for Colten Teubert, a 2011 first-round pick and a conditional 2012 third-round that was used to pick Danhil Zharkov, who never played an NHL game.
Tuebert, a right-shot defenceman, only played 24 NHL games, all for the Oilers, where he picked up an assist in 24 games with the Oilers in 2011-12. However, that 2011 first-round pick turned out to be important, as the Oilers selected Oscar Klefbom. Playing 378 games, all with the Oilers, Klefbom scored 32 goals and 156 points, along with two postseason goals, before officially retiring in Aug. 2024 after not playing since the end of 2019-20.
With Klefbom retiring, the Mark Messier trade tree came to an end. Talk about a wild ride. 
If you enjoy my content, you can follow me on Twitter @Ryley_L_D.