Now both are out of jobs, part of a dramatic Broad Street breakup Sunday designed to jolt the NHL-worst Philadelphia Flyers out of the cellar and end their worst start in 17 years.
Clarke resigned in his second stint as general manager, unable to match the Stanley Cups he won with the team as a Hall of Fame centre in the 1970s. Hitchcock was fired more than a month after signing an extension, but with the Flyers 1-6-1 and with the fewest points in the NHL.
"I no longer wanted to make the decisions general managers have to make," said Clarke, long synonymous with the Flyers. "I felt it was time to step back."
Assistant John Stevens was appointed head coach and former Flyers coach Paul Holmgren was promoted from assistant general manager to interim general manager - the latest combination in an attempt to end a 31-year Stanley Cup drought.
Stevens, a former Flyer who coached the team's AHL affiliate, will be behind the bench when the Flyers play at home Thursday against Atlanta. He led the Phantoms to the Calder Cup championship in 2005 with many of the players now on the roster.
"We're very confident we can turn this thing around," Stevens said.
Even with Stanley Cup championships elsewhere on their resumes, Clarke and Hitchcock, close friends, never found the right mix together to bring a title to Philadelphia. The Flyers reached the Stanley Cup final under Clarke in 1985, 1987 and 1997. This year's team is miles from such a destination.
Flyers chairman Ed Snider said he decided to fire Hitchcock after a 9-1 loss to Buffalo last week, one of the worst in the franchise's 40-year history.
"We don't expect miracles, but we're hoping for a lot better results," Snider said.
While Clarke was given parts of 19 seasons in charge to win a Stanley Cup, Hitchcock had a considerably shorter stick. Only in his fourth season with the Flyers, Hitchcock signed a new deal in training camp through the 2008-09 season, so it was startling he didn't even finish this one.
"It's disappointing personally I wasn't given the opportunity to turn it around because I felt in my heart it was turning around," he said.
Snider acknowledged the Flyers had tuned out Hitchcock and his demanding style.
"I knew what went on," he said.
Clarke said the Flyers' record played no role in his resignation. He said he began feeling spent during last year's draft and hoped for renewed zest once the season started. That never happened, and Clarke said he decided to quit after the third game of the season.
"I felt strongly from the end of last season on, I don't know if the right word is burnt out or tired, but the decisions that had to be made, I was not willing to make them," Clarke said. "I was letting other people make them. I know I didn't do the right job for this organization."
As general manager, Clarke never matched the success he had as a Hall of Fame player when he led the Flyers to Stanley Cup championships in the 1973-74 and 1974-75 seasons. Clarke was in his 13th year in his second stint as general manager, after handling the GM role in the 1980s.
"When you're as close to someone as I believe I am, you recognize things. You see things. His mind-set hasn't been the same," Holmgren said.
Known for his "toothless grin," Clarke played for the Flyers from 1969-84 and captained the famed "Broad Street Bullies" teams in the 1970s. He immediately went from playing into management, holding the GM role from 1984-90. He returned to the position in 1994, famously feuding with Eric Lindros in 2000.
Philadelphia was bounced in the first round of the playoffs by Buffalo last season, and has seemed ill-equipped to win a Stanley Cup in an NHL where speed and scoring are now more valuable than the big, tough guys they've traditionally built around. Many of the same problems they had last season have lingered, notably a plodding defence that has yet to score a goal.
The Flyers waived three players last week after the blowout loss to the Sabres and Hitchcock even shuffled the lines, trying to anything to spark his sagging club.
"It's not going to be very far along before this team starts to win on a regular basis," he said.
In 10 NHL seasons with Dallas and Philadelphia, Hitchcock is 408-249-100. He is 66-51 in playoff games and won the Stanley Cup with Dallas in 1999. He led the Flyers to the conference final in 2004, where they lost to the Tampa Bay Lightning, who later won the Stanley Cup.
"It's not acceptable the start we had and I think the change needed to be done," Flyers captain Peter Forsberg said.
The Flyers are off to their worst start since another 1-6-1 start in the 1989-90 season, coincidentally costing Clarke his first shot as GM. The Flyers missed the playoffs that season, starting a five-year span without a post-season appearance.
The Flyers have to pick up the goal scoring if they want to make the post-season for the 12th straight season. They have only 15 goals in eight games - five by Simon Gagne. They are a woeful 4-for-55 on power-play chances this season.
"We're all responsible for what happened," Gagne said. "It's not only them. It's enough. We need to find a way."
Clarke and Hitchcock said they want to take a break from the game before returning, both even saying they would return to Philadelphia, if wanted.
"I would have never thought I'd get tired or burnt out or something. But this is what's happened," Clarke said. "I've got to try and figure out why and how."
Now Stevens and Holmgren take their turn, trying to figure a way to bring the Flyers back among the NHL's elite.