A pair of his greatest players -- bedrocks of the four-Cup dynasty -- were exiting Stage Right after herculean careers.
Denis Potvin decided to end his playing days following the 1987-88 season; and there were no ifs, ands or buts about it. In the spring of '88 -- depending on playoffs, -- the world's best defenseman would become an ex-Islander.
Bossy wasn't so sure. The urge to play; to score; to help his buddies make the playoffs was there; no question.
But there was one thing missing on Boss -- a good back, as opposed to his rapidly deteriorating bones that had cramped his All-Star style.
Following the club's seven-game series loss to Philadelphia in April 1987, Mike checked with virtually every available doctor specialist, non-specialist, chiropractor, you name it, to find a cure for his back woes.
The answer was the square root of nothing.
In his autobiography, Boss -- The Mike Bossy Story, he laments the fact that no cure was available. His medical list ran to the dozens as did his frustrations.
Bossy: "One doctor described my bad back as a condition common to people across the country. He didn't think there was anything he could do."
As for Potvin, The Captain unequivocally declared that some time in springtime, of 1988, when the birdies are warbling, he would remove his Islanders jersey for the last time and hang up his skates.
"I've done just about everything I can do," Denis announced. "I didn't want to play for one season too many."
Video: Denis Potvin was captain of Islanders' 1980s dynasty
Nor did the dynasty-builder feel like waiting around; Torrey already had begun to make constructive moves.
Bow Tie Bill traded Duane (Dog) Sutter to Chicago for a second-round pick while searching around for other deals that might help his team, long and short-range.
By the time the 1987-88 season got under way, the only remaining four-time Cup-winners on the team were Denis Potvin, Bryan Trottier, Ken Morrow and Bill Smith. Bossy, too, if you count the fact he was seeking pain-killers.
It had become time for change and for that reason -- among many -- the club held a secret, behind-the-scenes pow-wow to find a successor to Potvin as team captain.
There were the usual suspects including stalwarts such as Pat LaFontaine and Patrick Flatley, among others. But the players-only conference resulted in a mere two names on the ballot -- Bryan Trottier and Brent Sutter.
Sentiment and accomplishments should have made Trots the favorite. Instead after the votes are collected, Brent Sutter got the "C" barely edging out Trots who was given an alternate captaincy along with defenseman Steve Konroyd.
As the fourth captain in team history, Brent evolved into the very model of a quiet, tenacious and indomitable leader of men.
"Sutter's leadership in the dressing room was far-reaching," was the way one beat reporter noted. "For his relentless drive and stoic professionalism, Brent was willing to do anything."
That was good news for second-year coach Terry Simpson. a tough-tough loser, Simpson spent many hours of his summer vacation wondering why his club capitulated so crumbly in Game Seven at Philly.
Simpson: "That game (in Philadelphia) is a cross we all had to bear all summer. I hope it gets heavier before the new season starts."
In a sense, Simpson was fortunate that Captain-In-The Wings, Brent Sutter, shared every last one of the coach's sentiments. If nothing else, Brent would emerge as the most dependable player Terry had in the entire lineup.
One writer's Analysis: "Brent was able to juggle the chores of being the players' player and go-to guy for management. As a matter of fact, some of Sutter's teammates would jokingly refer to him as a member of the front office."
As for the front office, Torrey maintained his faith in Simpson despite the fact that such future Hall of Famers as Bossy and Smitty suffered disagreements with the sophomore bench boss.
Since Bossy was out with his chronic back injury, his anti-Simpson input was less stinging but Battlin' Billy was not doing cartwheels of joy as back-up to Kelly Hrudey.
Tough Western Canadian that he was, Simpson did it his way totally unconcerned -- shall we say oblivious -- to the perturbed stars and their petulance.
Starting the new 1987-88 season in Los Angeles, Terry won over Billy by starting him against the Kings and Smitty returned the favor, headlining a 4-1 win.
Other players jumped on the Simpson Bandwagon and after 20 games, the club's record was an awe-inspiring 14-5-1; best start for the Nassaumen since the 1978-79 season.
Minus Bossy, Simpson turned Mikko Makela into Trottier's right wing and the unlikely -- in every way -- pair clicked providing a one-two offensive punch.
When even productive players like Makela irritated the coach, Simpson disciplined them faster than a hammer can hit a nail.
Once, after an aching 5-2 loss to Toronto at Maple Leaf Gardens, Simpson accosted Makela, Brad Lauer and Gerald Diduck during the second intermission.
Although there remained a whole third period to play, the coach ordered the trio to take off their sweaters and remain in the dressing room. At least Makela got the message; he scored a career-record 36 goals that season.
By mid-season Simpson's had a two-pronged target range: 1. Gain a playoff berth; 2. Shoot for a first-place finish and home-ice advantage.
The first road detour sign read 2-7-2; ergo a pre-New Years slump that prompted Torrey -- on coach's advice -- to lighten the load with the demotion of two 1985 first round picks, Brad Dalgarno and Derek King.
if there were hurt feelings, too bad. Even the productive Pat LaFontaine was slighted when it appeared that Simpson would bypass him as the club's rep in the NHL All-Star Game.
Simpson: "I don't think we have an All-Star on this team. Al Arbour -- Radar who was named an "honorary" captain -- should be our only rep."
Wales Conference coach Mike Keenan disagreed -- bypassed Simpson -- taking LaFontaine and Denis Potvin as an honorary selection.
Nice guy that he was, Keenan noted that Potvin had recently (January 14, 1988) scored his record 300th goal. As for picking Patty, no explanation was necessary except that he remained one of the league's best centers.
Moribund as the Islanders may have seemed to Simpson's Argus eyes, there also remained a hidden sparkplug that, when ignited, would produce yet another breathtaking finish to the regular season.
What made the successful homestretch run even more astonishing is that it was accomplished after ever-reliable Patrick Flatley tore ligaments in his right knee and was lost for the season.
Torrey: "Our comeback from Flats' injury in early February to where we wound up at the start of April has to go down with one of the more underrate accomplishments of this franchise."
As it happened -- with perseverance and grim determination -- Simpson's two primary goals miraculously would be achieved.
LISTS: FOUR WAYS TERRY SIMPSON KEPT HIS TEAM A WINNER
1. SURPRISE REPLACEMENTS: One hardly could expect Mikko Makela to duplicate Mike Bossy's accomplishments alongside Bryan Trottier; yet the Flashy Finn finished the year with a commendable 36 goals. Not as productive but no less effective was 24-goal-man, Alan Kerr.
2. HAPPY GOALIES: Bill Smith adjusted to his back-up role and proved both mentor and inspiration to starter Kelly Hrudey. As a tandem they made beautiful music together.
3. LATE ADDITIONS: Once the 1988 Winter Olympics ended, gifted USA team defenseman Jeff Norton signed on with Torrey. He became one of the NHL's most fluid skaters. Toughie Mick Vukota was a free agent signee as well.
4. THE VETS DELIVER: Both Denis Potvin and Tomas Jonsson enjoyed solid seasons behind the blue line; an encouraging farewell season for the Captain.