Looking back at the top free agent signings by the Edmonton Oilers

Happy birthday Canada and happy NHL Free Agency! As all the news breaks around the hockey world of free agents signing all over the league, let’s revisit the top free agent signings by the Edmonton Oilers, in no particular order.

Charlie Huddy was an undrafted blueliner when he inked his deal with the Oilers in Sept. of 1979. The then-21-year-old was playing with Oshawa Generals of the OMJHL and after signing split his time between the CHL and NHL until joining the Oilers on a full-time basis in 1982.

Huddy didn’t just sign with the Oilers and play a few years, he became one of seven players who helped the Oilers win all five of the franchise’s Stanley Cups (1984, 1985, 1987, 1988, and 1990). Huddy played 11 years in the City of Champions scoring 81 goals and 368 points in 694 games. The defenceman made his place prominent in the organization when he and linemate Paul Coffey combined for one of the best defensive pairings in league history.

Much like Huddy, Dr. Randy Gregg was also an undrafted player when he signed a deal with the Oilers in Oct. of 1982. Gregg’s NHL story is fascinating. As a young 19-year-old, he decided to give University hockey a shot while working on his medical degree. He played for the University of Alberta Golden Bears, becoming one of the top players in the league, and helped direct the team to two Canadian Interuniversity Athletic Union Championships.

After signing with the Oilers, he emerged as a regular in 1982-83, and his NHL career took off. Aside from the fact that Gregg retired four separate times from the NHL, Gregg was a five-time Stanley Cup Champion, with the Oilers winning it in 1984, 1985, 1987, 1988, and 1990. In 1990 he was claimed by the Vancouver Canucks in the waiver draft and played 21 games with them in 1991-92. In his nine years in the NHL, Gregg scored 41 goals and 193 points over 474 games and became a doctor.

In early January of 1984, Craig MacTavish was involved in a drunken incident that took the life of another driver. He was charged with vehicular manslaughter, and while serving his time jail, he became a free agent signing with the Oilers in 1985.

MacTavish was a previous member of the Boston Bruins, where he played for five years watching the Oilers hoist the cup twice before his arrival. When he arrived in Edmonton and played his first season since his sentencing, he surpassed his numbers produced in Boston, scoring 23 goals and 47 points in 1985-86. MacTavish won three Stanley Cups in Edmonton (1987, 1988, and 1990) and eventually took on the role of captain following the shocking Wayne Gretzky sale in 1988 and the Mark Messier trade three years later in 1991.

MacTavish remained with the team before being traded to the New York Rangers in March 1994 in exchange for Todd Marchant and won his fourth Stanley Cup that year with the Rangers. He signed with the Philadelphia Flyers for a short two-year stint after the win in 1994 and then was traded to the St. Louis Blues in 1996. He spent nine of his 17-year NHL career in Edmonton, scoring 155 goals and 331 points in 701 games.

On Canada Day in 2001, the Oilers traded their all-star captain Doug Weight to the St. Louis Blues, resulting in Steve Staios inking a multi-year deal in the City of Champions just 11 days later. The signing would mark the fourth NHL team Staios would bare on his jersey in his six years in the league after making stops with the Boston Bruins, Vancouver Canucks, and Atlanta Thrashers.

He quickly became the Oilers’ unsung hero in Edmonton winning that award after his first season notching 10 points and a plus-10 rating. He played his best year in his career in 2003-04, just ahead of the NHL lockout, for a career-high of six goals and 28 points with a plus-17 rating. He would match his career-high season after the 2004-05 NHL lockout and helped the team battle through the heartbreaking 2006 Cinderella Cup run.

He scored 35 goals and 146 points over the eight years he spent in Alberta’s capital and sported the ‘A’ on his jersey for five of those years. In 2010, the Oilers traded him to the Calgary Flames in exchange for a third-round pick in 2011 and Aaron Johnson marking the first time the rival teams had made a deal. He played one more year in Calgary before going to the New York Islanders for the 2011-12 season and retired the summer after.

Marc-Andre Bergeron was another top undrafted player the Oilers signed through free agency. In July 2001, he signed the papers and headed to the City of Champions.

Bergeron is remembered by many people for unintentionally driving Carolina Hurricanes forward Andrew Ladd into the net, sending both himself and Ladd crashing into Oilers netminder Dwayne Roloson during the final minutes of game one of the 2006 Stanley Cup Final. Roloson wouldn’t see playoff ice for the rest of the year after injuring his knee during the collision, and we all know how it ended for the Oilers.

Bergeron had the best season of his career with the Oilers in 2005-06. He scored 15 goals and 35 points with a plus-3 rating playing a part in the Oilers Cup run. After another good season the following year, he was traded to the New York Islanders in 2007. Before retiring in 2017, he went through five more colours of threads, playing for the Anaheim Ducks, Minnesota Wild, Montreal Canadiens, Tampa Bay Lightning, and the Hurricanes.

You can file Nikolai Khabibulin under the “random players who played for the Edmonton Oilers.” Khabibulin signed with the Oilers as a free agent on this day in 2009 having spent his career up to that point with the original Winnipeg Jets, who drafted him in the 9th round of the 1992 draft, and followed them to Phoenix. He inked a four-year, $3.75-million AAV deal.

Later stints brought him to Tampa Bay and eventually Chicago, before landing in Edmonton at 37-years-old. His debut with the team came on Oct. 3rd that year, but ended in disaster mishandling a puck and allowing Calgary Flames winger Davis Moss to score the winner. By the following January, he had surgery on a herniated disc in his back and injuries followed him into his second year, too.

Khabibulin had a strong start to the 2011-12, but his numbers fell off towards the second half of hte season. In his final year with the Oilers, the lockout-shortened 2012-12 season, he played just 12 games backing up Devan Dubnyk. He signed with Chicago the following year, and retired after that campaign.

On this day in 2016, the Oilers signed veteran forward Milan Lucic to a seven-year deal with a $6 million AAV. The 27-year-old played most of his career as a Boston Bruin, scoring 139 goals and 340 points over eight years with the team. He was traded in 2015 to the Los Angeles Kings in exchange for 1st round draft pick in 2015 (Jakub Zboril), Martin Jones, and Colin Miller. That offseason, he decided to test free agency leading to his signing with the Oilers.

His first year with the Oilers was by far his best in his three years in Alberta’s Capital City. The 28-year-old scored 23 goals and 50 points while bringing his gritty edge to the game. He scored 10 goals and 34 points in his second year, while his third slopped down to six goals and 20 points. He gave the Oilers two good years of hockey and was a part of the team that brought them out of the decade of darkness, but a seven-year contract was pushing it. The organization traded him in July 2019 to the Calgary Flames with a 3rd round draft pick in 2021 (Kirill Kirsanov) in exchange for James Neal. This year finally marks the last of his contract being paid off by the Oilers and earlier today he signed a one-year deal to return to the Boston Bruins.

The Edmonton market felt unsure when the rumours swirled that veteran-forward Evander Kane was conversing with Ken Holland in January 2022. Kane’s contract with the San Jose Sharks had been terminated after he violated COVID-19 protocols in the AHL.

When it was announced that Kane had signed a one-year contract worth $2.108-million, everyone wanted an opportunity to voice their opinions because at the time of Kane’s arrival, he was a controversial player.

Still, for the Oilers, it meant more secondary scoring and an addition to their top six. Kane has flourished since being in Edmonton and inked a four-year at the end of the 2021-22 season with an AAV of $5.125-million. By the end of this past season, Kane had 16 goals and 28 points over 41 games, with an additional three goals and five points during the playoffs. Aside from some meme-worthy playoff moments, Kane had his first of a handful of injuries this season, starting with having his wrist accidentally stepped on by Tampa Bay Lightnings’ Patrick Maroon, then breaking his ribs in February, and finishing with a broken finger during playoffs. Next year Kane is expected to return healthy and get back to his usual point-producing ways within the Oilers’ top six.

A year ago today, the Oilers signed goaltender Jack Campbell to a five-year, $25 million deal. Things haven’t exactly gone according to plan for the netminder.

He had a good campaign in 2021-22 posting a 31-9-6 record and .914 save percentage with the Leafs, but he fell off this cliff in his first year in Edmonton. While his 21-9-4 record was solid, his .888 save percentage and 3.41 GAA was far from where it needs to be.

Drafted 11th overall by the Dallas Stars in 2010, Campbell’s career took off when he was traded to the Los Angeles Kings in 2016 for Nick Ebert; at 27 years old, Campbell played in 31 games in 2018-19 with a record of 10-14-1. After a slow start to the season with the Oilers this year, Campbell found his groove during a stretch in early 2023, but his game fell apart again not long after. The netminder backed up rookie goaltender Stuart Skinner for the Oilers’ 12-game playoff run this year.