So look where it got him: In Buffalo of all places, preparing to face the league's top-seeded Sabres, who happen to be the team he formerly coached.
"It's funny how life works sometimes," Nolan said Wednesday, a day prior to opening the best-of-seven first-round series in Buffalo.
Not that Nolan's spending a lot of time laughing or catching up with old acquaintances.
"I'm trying to come up with a game plan to beat this high-powered offence," he said. "We're going to have our hands full."
The Islanders (40-30-12) are viewed as the prohibitive underdogs after sneaking into the post-season by winning their final four games to clinch the Eastern Conference's eighth and final berth. And they'll play Game 1 minus star goaltender Rick DiPietro, who hasn't been cleared to play after sustaining two concussions last month.
Minor league backup Wade Dubielewicz, who closed the season with four wins, will start instead.
The Sabres (53-22-7), by comparison, have been on a season-long roll in finishing with the NHL's best record. They closed by going 9-3-1, led the league with 308 goals, and are the healthiest they've been all year after forwards Maxim Afinogenov and Tim Connolly returned from injuries last week.
The Sabres' roster is so deep that their so-called third line combined for 87 goals: Thomas Vanek with a team-leading 43, followed by Afinogenov (23) and Derek Roy (21).
"Our strength is our secondary scoring, which I really believe can be found on all lines," coach Lindy Ruff said. "I think sometimes opponents have to pick their poison."
Goaltender Ryan Miller added there's no secret to what will allow the Sabres to carry over their success into the post-season.
"If we play good hockey and play together and play with energy, we're nearly impossible to beat," said Miller, who won 40 games to set a franchise record.
The Sabres won three of four meetings against New York, including a 6-4 win on March 30. The team also returns with the core intact from the group that reached the Eastern Conference finals last spring, when Buffalo lost Game 7 to Carolina, the eventual Stanley Cup champion.
The Sabres, however, raise numerous reminders of why they're not looking past the Islanders.
There's last year's playoffs, when top-seeded Detroit was upset in the first round by Edmonton. And no team since Detroit, in 2002, has won the Cup when finishing first in the regular season.
"We want to make sure the confidence is there, but we want to make sure it's not overconfidence," Sabres co-captain Daniel Briere said. "We worked hard to get the No. 1 seed, and we want to use it to our advantage. We don't want to blow it in the first game."
The Islanders are in the playoffs for the first time since 2004, but haven't advanced past the first round since reaching the conference finals in 1993.
New York has been led by Jason Blake, who scored 40 goals and added 29 assists, and the team bolstered its lineup by acquiring offensive forward Ryan Smyth in a deal with Edmonton at the trade deadline in February.
They've been streaky at best this year. New York's four-game win streak to end the season matched its longest of the year, but was preceded by an 0-3-1 skid.
The series features numerous subplots, the most intriguing Nolan's return after his tumultuous departure in the summer of 1997. Replaced by Ruff, Nolan left the team after two seasons and after being named the NHL's coach of the year, unhappy when the Sabres offered him a one-year contract.
No hard feelings.
"Let bygones be bygones," said Nolan, who didn't coach again until guiding Moncton of the Quebec Major Junior Hockey League last season. "Buffalo will always have a special place in my heart. But now we have to try to beat their hockey team."
Sabres general manager Darcy Regier, who offered Nolan the one-year deal, is fine, too.
"It's 10 years ago. He certainly deserves to be coaching in the National Hockey League," Regier said. "And he's done an outstanding job with that team."