His teams made the playoffs in eight of nine seasons from 2002 through 2011 before his teams in Arizona struggled to compete due to financial constraints. Most recently, he was a senior adviser for the NHL's Seattle expansion franchise, helping to design its revamped arena and build out the hockey operations department.
He didn't go to Seattle to become the team's coach, but the idea started to intrigue him as his competitive fires started burning again. But with Seattle not entering the league until 2021, the wait to be a coach would have been too long for him.
The Oilers, however, had a more immediate opportunity, with newly hired general manager Ken Holland looking for a replacement for coach Ken Hitchcock, who took over the team midseason and assisted in the hiring process after the season.
Both kept circling back to Tippett as the best candidate, and they signed him to a three-year deal. They liked the structure with which his teams played. They liked the results he had gotten in previous stops in the NHL. But mostly, they liked his experience.
"I'm big on experience," Holland said. "When you're in the NHL, there are always some choppy waters. You have to be steady on the rudder."
The waters aren't just choppy in Edmonton. Using that analogy, the Oilers are hockey's worst Jacuzzi. They've made the playoffs once -- McDavid's second season -- since 2006, and thus far they have squandered their chance to contend with the best player in the world on their roster.
Tippett sees the Oilers as more than a two-man team, with the 22-year-old McDavid and Leon Draisaitl. He said he sees a team that should follow the template of the two teams in the Stanley Cup Final, the Boston Bruins and St. Louis Blues.
"Sound defensive teams," said Tippett, "but teams that allow their players to flourish with the puck."
But when it comes to the big two, Tippett said he likes to see McDavid, who has a deal that runs through 2025-26 with a $12.5 million cap hit, and Draisaitl playing together.
Tippett said the two on the ice together reminds him of when he coached McDavid as an assistant with Team North America in the World Cup of Hockey in 2016 and Auston Matthews was added to McDavid's line as a winger.
"I like seeing them together. It seems like they feed off each other," Tippett said. "That being said, I'm not stuck on that. I want to see how the rest of that lineup looks."
Many are curious what the Oilers will look like under Tippett. His teams in Arizona were known for smothering defense. After Hitchcock, have the Oilers gone for a second straight veteran defensive coach?
Tippett pushes back against that label.
"I laugh at that all the time. My first [head-coaching] job in the NHL I got because I was an offensive coach," Tippett said, referring to being hired in Dallas after serving on the Los Angeles Kings' staff. "Then I went to Arizona and I have to figure out how to win without those high-end scorers."
He has them now in Edmonton, and Tippett's message at his introduction was clear: He's going to apply his philosophies to the team he's been given.
"I don't look at myself as a defensive coach or an offensive coach," Tippett said. "I look at myself as a coach that tries to find a way to win with the people that I have."
With that, the focus returns back to Holland, who will be tasked with trying to find the people with whom Tippett can win.