MIAMI -- The last time Pat Riley faced the end of an era like this, his back was literally against the wall.

Prolonging the inevitable burned Riley when he last tried to squeeze a last-ditch loyal run out of the remains of his first Miami Heat championship team in 2006. Apply the bitter lessons learned back then to now, and perhaps it's understandable why a clean break from Dwyane Wade was the move to make.

Miami's magical Big 3 era technically ended two seasons ago when LeBron James bolted back to Cleveland. Couple that with Wade's stinging departure last week in free agency to Chicago and the uncertainty of Chris Bosh's medical condition moving forward, then it's conceivable that no one from the most accomplished trio in franchise history will ever score a point in a Heat uniform again.

Riley can move on with a heavy heart but a clear conscious now because the alternative is desperately holding on too long like he did nine years ago.

Back in the 2007-08 season, in a desperate move to shake up a roster that had grown stale around an aging Shaquille O'Neal and an injured Wade, Riley offered an invitation into his soul after a practice at AmericanAirlines Arena during what would be his final season in the dual role of team president and coach.

This view of one of the most relentless, ruthlessly successful and maniacal executives in NBA history would be as clear as the picturesque Biscayne Bay just outside of the Heat's practice facility.

"You all know me," Riley told a small group of reporters at the time. "I'm always pushing my chips into the center of the table. You want to make a deal? Let's make a deal. Let's go all in. How far do you want to go? I'm always willing to see how far we can push it -- to the absolute max. What is it going to take?"

That approach has driven Riley through a Hall of Fame career that has seen him -- in one role or another -- collect NBA championship rings for all but one finger. Yet in this instance, the riverboat gambler in Riley drove him directly into a trade for Ricky Davis and Mark Blount.

The intent was to salvage one last productive season out of a disinterested O'Neal, and to reinforce the roster with a perimeter scorer to carry the load on nights Wade required injury rest or rehab.

Oops.

Pour Riley a glass or three of his preferred wine and play just the right rhythm-and-blues vinyl record to reflect his mood, and he might admit that his ego, ambition and pride got the best of him in what led to an injury-riddled, frustrating 15-win season that stands as the worst in his 21-year Heat tenure.

Back in 2006, Pat Riley and Dwayne Wade celebrated the Heat's first championship. Andrew D. Bernstein/NBAE via Getty Images

Before now, that decision stood as the most recent example of Riley launching the franchise into a massive rebuilding process. Until now, he always has had the benefit over the past 13 years of putting the pieces back together with Wade as the foundational rock.

The same intestinal fortitude, intensity and entitlement that steeled Riley and Wade together through five trips to the NBA Finals, the most successful four-year run in franchise history and three championships are the character traits -- and flaws -- that eventually ripped them apart.

"I will always love Pat, and I know he feels the same way about me," Wade said over the weekend during an appearance at his youth basketball camp in Miami. "He's a tough cookie. And I've grown into being a tough one as well. Yeah, we can butt heads at times."

That's Wade admitting that he and his professional father figure and mentor are more alike than different. In fact, their similarities are what made it impossible to turn back once they had their differences.

In what ultimately amounted to a $3 million difference in bitter contract negotiations forced Wade to stand on pride and leave behind a legacy in Miami for a two-year, $47 million deal with the Bulls. And in what amounted to a weekend binge to move the franchise forward, Riley executed a flurry of signings with the $20 million in 2016-17 salary cap space earmarked for Wade.

Forget the facts, for a second. It's the optics that make this divorce overwhelmingly depressing a week later in the aftermath. If you're Riley, how do you justify matching a $50 million contract to retain undrafted, second-year guard Tyler Johnson and balk at giving Wade the $50 million he sought to stay? When Goran Dragic showed up last season admittedly out of shape after signing a five-year, $85 million contract, it was Wade who provided his healthiest season in five years by playing in 74 games. Hassan Whiteside secured a four-year, $98 million contract as Riley's No. 1 priority in free agency on July 1.

The partnership between Pat Riley and Dwyane Wade brought three titles to Miami. Joe Murphy/NBAE/Getty Images

But it was Wade who nearly pushed the Heat to within one game of reaching the conference finals as Whiteside was sidelined with a knee injury midway through the second-round series against Toronto. Simply put: Wade was the Heat's best player last season, and also would have been next season. He felt he should have been paid as such. Or at least right behind only Bosh's $23.7 million salary.

On the other hand, if you're Wade, how do you still hold a grudge for never being the Heat's highest-paid player in any season when the reality is you netted the max allowed on the rookie deal and extension through your first seven seasons? Then, when James and Bosh arrived in 2010, all three took less over the next four years until they each opted out in 2014. In retrospect, Wade bypassing the final two years and $42 million on his original big three contract proved as regrettable as the mistake Riley made six years earlier when he miscalculated Shaq's competitive hunger and Wade's health.

The irony is that had James, Wade and Bosh played out the completion of their 2010 Miami contracts, they would have reached the finish line this summer. But an era that opened with such hope and promise is on the verge of ending in pain as it pivots toward a necessary roster reboot.

Six years ago, as James, Wade and Bosh were raised onto a stage to introduce their unprecedented union to the sports world, few could have honestly imagined it would splinter apart at the finish quite like this. And if we were told only one member of that trio would still be on the roster six years later, there's no doubt Wade would have been the unanimous assumption.

If there's one other thing Riley and Wade have in common, it's that they don't do breakups well. There's a trail of strained or ruined personal and business relationships alongside the championships and personal triumphs in their respective and collective wakes along the way.

What Riley eventually proved in the face of past personnel mistakes is that, given time, he'll steer the franchise back onto a championship contending course. But at age 71 and likely facing retirement soon, Riley lacks the time and patience he enjoyed a decade ago. Now, his back is figuratively against the wall heading into the toughest rebuild yet.

Riley has never lacked the will to forge a way forward in Miami.

Only this time, he no longer has a Wade.