CHICAGO -- It was October 2008, on a picture-perfect autumn day, when

steered his Range Rover through a Portland suburb and spotted someone at a bus stop wearing a black Trail Blazers jersey.

McMillan had spent 14 hours with a reporter that day, running errands, watching film, coaching practice and talking at length about the promise of the Blazers' young, talent-rich team. Times had been rough for the Blazers in recent seasons, but McMillan, who had been hired to rescue them from the painful "Jail Blazers" era, was hopeful he was the coach that would give basketball-crazed Portland a championship and restore Rip City to a once-proud franchise.

"See that," McMillan said at the time, pointing at the man in the jersey. "It's coming back. Rip City is coming back."

But it didn't stay long.

During a whirlwind Thursday that will no doubt be remembered as a turning point in Blazers history, owner Paul Allen fired McMillan after six-plus seasons and named one of his assistants, 33 year-old Kaleb Canales, interim coach. The move was part of a shake up that also saw the Blazers

and

from the roster -- including former No. 1 overall draft pick Greg Oden -- signalling the start of a complete overhaul.

"This is a defining moment of a new direction for this team and this organization," Blazers President Larry Miller said during a Thursday night news conference in Portland.

McMillan's firing caught several Blazers executives and most of the coaching staff by surprise. The news first broke shortly after the NBA trade deadline had passed at noon, and when one assistant coach was contacted for comment via text message, he replied: "News to me."

But others had seen the writing on the wall for some time – including McMillan himself. Quietly, behind the scenes, McMillan acknowledged that if the underperforming Blazers didn't improve, he expected to take the fall. The Blazers (20-23) are perhaps the NBA's biggest disappointment this season, sitting in last place in the Northwest Division and 11th place in the 15-team Western Conference. They have lost seven of their last nine games, with all six of their March defeats coming by double digits.

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Pressure began to mount during these lopsided losses, and Miller said he and McMillan talked "multiple" times over the last week about McMillan's job status and the performance of the team. The final straw came Wednesday night, when the Blazers were humiliated 121-79 to the New York Knicks, suffering the fifth most-lopsided loss in franchise history.

McMillan’s players publicly supported him after the defeat, but it was clear a segment of the locker room had long ago tuned him out or, worse, quit on him. So Miller and interim general manager Chad Buchanan discussed McMillan’s future Thursday, and Miller said the two decided to recommend to Allen that he let McMillan go. Allen agreed.

McMillan did not respond to multiple interview requests from The Oregonian on Thursday, but Miller -- who broke the news to McMillan over the phone -- said the former coach was "taken aback" but "gracious and professional as always."

"Nate was not happy with where things were," Miller said. "I think he understood that the team was not putting out the kind of effort that he wanted to see, that any of us wanted to see. And he acknowledged that."

McMillan, 47, finished his Blazers tenure with a 266-269 record in just under seven seasons. It's the second-longest coaching stint and third-most wins in team history. But, like every Blazers coach but Jack Ramsay, McMillan also leaves without delivering Portland a championship.

It's hardly the exit many envisioned years ago.

The Blazers plucked McMillan, affectionately called "Mr. Sonic," away from the then-Seattle Supersonics before the 2005-06 season hoping that his no-nonsense approach and Old School reputation would be the perfect antidote for a struggling franchise trying to move on from the Jail Blazers era.

McMillan instantly took control of a loose locker room, led by Darius Miles and Zach Randolph, with demanding two-hour practices, drill seargent-like instruction and a requirement to work hard at all times. Randolph quickly dubbed him "Sarge."

The Blazers struggled his first season, finishing with the worst record in the NBA, but the groundwork for a transformation had been established. By the time the 2008-09 season rolled around -- when McMillan spotted that Blazers fan at the bus stop -- the Blazers were a team on the rise and the talk of the NBA.

With three potential superstars in Brandon Roy, LaMarcus Aldridge and Oden, most pundits predicted years of playoff success and, eventually, championships. But injuries, which will define McMillan's Blazers tenure as much as anything, sabotaged those hopes.

Oden would play just 82 games over five seasons as five separate knee surgeries ruined his career. And after developing into one of the game's best players under McMillan's tutelage, Roy also would encounter career-ending knee trouble. He retired on the eve of training camp this season.

From 2009-11, the "Frail Blazers" were besieged by injuries, epitomized by a 2009-10 season in which players racked up an astounding 311 games missed because of injury. Even so, reflecting the never-say-die, hardworking persona of their coach, the Blazers defied odds and won 50 games. They went on to lose in the first round of the playoffs, however, which was another reality that haunted McMillan during his tenure in Portland.

The Blazers have been one of the NBA's most successful regular season teams in recent years, winning 54, 50 and 48 games each of the last three seasons. But they also lost in the first round of the playoffs each time as McMillan and his staff were outcoached and outmaneuvered by the likes of Rick Adelman and Rick Carlisle. Critics chided McMillan for having a predictable and unimaginative offense and criticized his inability to make in-game adjustments.

Even if the Blazers hadn't underperformed this season, McMillan likely would have faced heat with another first-round playoff exit. Last month, when the season started to go south, McMillan told The Oregonian, "Sometimes if you go down, you are going down your way."

And there's no question McMillan went out his way. He never publicly threw any of his disgruntled players under the bus and he never stopped fighting to make the Blazers better. In the end, though, the Blazers' struggles were too much to ignore, particularly on a day in which Buchanan and Miller gutted the roster to make room for a rebuilding project.

"We decided that if we're going to make this kind of move, let's just do it now and move on," Miller said. "These are always difficult decisions to make. The timing we just felt was right to set this new direction for the team."