A native of Minneapolis, Minnesota, the former Minnesota North Stars, Edmonton Oilers, and New York Rangers defenceman has followed up his formidable nine-year National Hockey League (NHL) career from 1978-87 in the coaching ranks across North America and Europe in the proceeding 29 seasons.
Jackson played his role as a defensive defenceman behind the likes of Paul Coffey, Glenn Anderson, Wayne Gretzky, Mark Messier and Jari Kurri on the ice for the Oilers from 1981-86. As a coach, his name has become synonymous with championships in his adopted country of Germany.
Eight league titles in 11 seasons, an exceptional rate of success in any league, can do that.
"They're still not easy," he said.
Jackson spent the first four seasons of his career jumping between the NHL's North Stars and their minor-league affiliate in Oklahoma City before being traded to the Oilers at the onset of the 1981-82 season.
"I was being traded from my hometown, which was a bit of a shock," Jackson said of the move. "But at the same time, I knew I was coming to a young team. I still wasn't fully familiar with the likes of Paul Coffey or Mark Messier being that I spent three or four years in the minor leagues before I arrived, but I knew I was coming to a good club."
The former blueliner's career at this junction could have taken a dramatic turn as he considered a career outside of hockey in real estate.
"I had given myself a short time to make it in the league before making another decision on my career," Jackson said. "Economies weren't very good at the time and the job market wasn't great, so I took a week to think things over before deciding I needed a paycheque and coming to camp in Edmonton."
Spending the majority of the following season playing for the Wichita Wind, Edmonton's Central Hockey League affiliate, Jackson earned his break in 1982 as a bottom-pair defenceman when the Oilers began establishing themselves as one of the league's budding rosters.
He found a role as a shutdown defender alongside regular partner Randy Gregg among the star-studded cast of the Oilers at the time. Never amassing more than 20 points in an NHL season, Jackson stuck to his role and fought when needed to protect his teammates, often times simultaneously with Dave Semenko.
"I always considered myself to be one of those sixth defencemen and one of those guys that needed to perform certain roles on the team to stay there and contribute," he said. "With that, I just felt during practices and competing against guys like Gretzky, Kurri and Messier gave me a huge opportunity to become a better player."
Falling short in the second round of the 1982 NHL Playoffs against the Los Angeles Kings and the Stanley Cup Finals a season later against the New York Islanders provided necessary lessons for an ambitious Oilers team that was setting the foundation for one of the league's greatest dynasties.
"I thought for the club to come off the year they had previously that included the 'Miracle on Manchester' and then coming around to make it to the Stanley Cup Finals the next year was a big step," Jackson said.
An aging New York Islanders dynasty gave way for the young Oilers in 1984, with Jackson earning his first of two Stanley Cup rings in a 4-1 series win.
"As was documented and heartfelt was that we learnt a lot from the Islanders," he added. "They were aging, we were maturing, and it just so happened that we got matched up against them in the Finals, which couldn't have been a better matchup for the history of the game."
After being traded to the Rangers in 1986, Jackson retired the next season before beginning his coaching career with the East Coast Hockey League's (ECHL) Knoxville Cherokees in 1989. Sixteen years later, as an assistant coach with the Ottawa Senators, the 2004-05 NHL lockout served as the catalyst for another crucial and defining moment in his career.
Europe came calling.
"That lockout season left the Ottawa staff without jobs," Jackson said. "Coincidentally, I got invited by Red Bull to come and consult in Salzburg during their first year in a team sport."
Jackson was then brought to Germany in February of 2005 as an assistant with Eisbären Berlin, who'd win their first championship that season winning three games to one over Adler Mannheim.
Two seasons in Düsseldorf at the helm of the DEG Metro Stars led him back to Berlin and a head coaching role there, yielding plenty of success for both Jackson and Berlin in the form of five championships in six seasons from 2007-13.
"It was definitely an adjustment. Learning and adapting to circumstances is the key," he said of his transition to coaching in the DEL and early success. "Between every league in the world, there's always a bit of a cultural difference, not just in the culture itself but the style of hockey. So when you go to Germany, Sweden, Finland, or even Russia and Switzerland, there's always some difference in the style of hockey. Same goes for the NHL."
The next season, in 2013, Jackson moved back to Austria and EC Red Bull Salzburg, coming within one game of capturing his fourth-consecutive championship. The organization quickly brought Jackson back to Germany, this time to head up their flagship team in Munich.
The results should have been expected - four more German league titles in four seasons from 2014-18, embracing much of the same structure and tactics that made the Oilers successful three decades prior.
"Guys like Gretzky, Messier, Coffey and Kurri were natural leaders and that's kind of how I framed those guys to this point in my career," Jackson said. "They made me feel important, and over 30 years later as a coach, those are the kinds of players I'm looking for and paying attention to when recruiting.
"Character and leadership are the foundations for any organization."
The fast, free-flowing style of the Oilers in the '80s can still be seen present day in Jackson's coaching philosophy and across the DEL as a league.
"It's the kind of hockey we pride ourselves on playing," he continued. "Guys will talk about what a good league it is here. Germany winning a silver medal in the Olympics, and the type of personnel that has come into the league over the past decade has helped German players. There are some excellent players playing overseas like Leon Draisaitl."
Jackson's seen first-hand the buzz, and the boost, Oilers centre Leon Draisaitl has made in advancing German hockey over his nearly 15-year career coaching in central Europe.
"He played his junior years in North America, so the end of his development was constructive there," Jackson said. "But he played his earlier years in Mannheim which is a great organization committed to the development of players, so I think that helped him a lot. Plus, there's no doubt he has the skill level and determination to be successful."
With the Oilers facing Draisaitl's hometown team in the Cologne Sharks on Wednesday morning at 8:00 AM MT before beginning their NHL campaign in Gothenburg, Sweden against the New Jersey Devils on Oct. 6, Jackson says the Oilers can expect to be pushed by a strong, conditioned German side for the entire 60 minutes.
"Number one is they're going to play really hard," he said. "Number two is that the skill is good. Generally, the difference is in the level of speed, and Cologne are already six weeks into the regular season. They'll have their hands full.
"There's been several NHL teams that have played here in the past from the start of their training camp to when they get themselves geared up and ready to play a regular season schedule. They've become competitive games and fun to watch."