Playoff appearances have been few since the glory days of the 1980s. Coaching changes and chaos, however, have been abundant.
With a recently retired backup goalie now running the show from the front office, and DiPietro about to begin an unprecedented 15-year playing contract, some stability might be coming to Long Island after all.
"I think the biggest thing for us coming into camp was to use these exhibition games to really find out who we were as a team," said DiPietro, the Islanders' top goalie who will be under contract until he's nearly 40.
DiPietro became the first goalie ever taken with the No. 1 pick in the NHL draft when the Islanders selected him in 2000. Since then, he has played for five coaches in New York. And he just turned 25.
Thursday night's opener at Phoenix will see No. 6 come on board, and it's Ted Nolan - a former coach of the year who hasn't held an NHL job since being fired by the Buffalo Sabres after his award-winning season in 1997.
With Butch Goring, Lorne Henning, Peter Laviolette, Steve Stirling and Brad Shaw running the bench, the Islanders developed a reputation of not necessarily going full throttle every game.
"Last year, I don't think we had the consistency in our work ethic," DiPietro said. "It seemed like things would start to go wrong and you would start to get the snowball effect rather than picking our heads up and battling back."
After seven straight non-playoff seasons, New York got back to the post-season twice under Laviolette and once under Stirling. But the three-year run ended after the lockout.
"We were a hardworking team I just don't think we showed it every night," forward Jason Blake said. "That's probably why we got labeled that our work ethic wasn't up to par."
That and the lack of consistent victories led to Stirling's dismissal last season. Shaw held the position the rest of the way until Nolan was hired in June.
"He's great, he really is," Blake said. "He said, 'This is just how it's going to be."'
Suddenly, change that was so familiar around the team in a negative sense started to take an upbeat feeling.
Along with Nolan, the Islanders introduced new general manager Neil Smith, best known for building the Rangers' Stanley Cup championship team in 1994. But Smith quickly showed an inability to work in team owner Charles Wang's new front office by committee, and was gone just weeks later.
Without missing a beat, Wang tabbed backup goalie Garth Snow as the new GM - giving him the chance to hang up his skates and move into the boss' chair.
Before Smith was dismissed, he made several splashes in the free agent market. Smith signed Mike Sillinger to a three-year deal after he came off a 31-goal season; hard-hitting defenceman Brendan Witt, who also agreed to a three-year contract; offensive-minded defenceman Tom Poti; and forwards Chris Simon and Andy Hilbert.
"We want to be known as a working team, which hasn't been done the last couple of years," Nolan said. "Bringing those guys on is kind of rubbing off on everyone else.
"When you don't make the playoffs, there is a reason for it. We looked at the conditioning aspect, we looked at the leadership aspect, we looked at all those types those things and we addressed those couple of things."
Nolan used the pre-season to evaluate what he has on the bench. He quickly decided to keep enigmatic forward Alexei Yashin as captain following a season in which the centre had 28 goals and 66 points.
"Alexei is our leader," Nolan said. "For what he's been through the last couple of years, you have to support a guy. Nobody does it by themselves. He seems to be enjoying the game and having a lot of fun."
What was so often thought to be "Yashin's Team" has now shifted to one in which DiPietro is being groomed to lead. Yashin still has five years left on a 10-year deal, exceeded in length only by DiPietro's stunning new US$67.5 contract that runs through 2021.
For now, DiPietro will be backed up in goal by journeyman Mike Dunham, a former college teammate of Snow's at Maine who signed a one-year deal last weekend.
"As far as Ricky, he's our guy but you also have to have maturity around him," Nolan said. "Dunham is a classy individual as the other guys we've brought in.
"You win not just with talent but good people."