But as free agency opens just after midnight Tuesday, the question is whether the accomplished and proud 69-year-old veteran executive can assemble another masterpiece similar to the success he had four years ago when bringing the Big Three together.
There should be absolutely no doubt about the answer.
Riley didn't need to recite the finer points on his decorated resume during his stern and stoic season-ending news conference after San Antonio demolished the Heat in five games during the NBA Finals, which emphatically ended Miami’s quest for a third straight title.
But the tone Riley set weeks ago during the first five minutes of his hour-long plea for perspective and call for James, Wade and Bosh to “stay the course” clearly resonated heading into a high-stakes July.
“I've been a leader and a decision-maker,” Riley said of a career that has included nine championship seasons as a player, assistant, head coach and executive over 45 years. “That's my level of expertise. I'll do everything in my power to retool this team. What cements a forever bond is going through what we went through this season and staying the course.”
A process that started with Riley's state of the union address three weeks ago continued in recent days when James, Wade and Bosh opted out of the final two seasons of their contracts to help create a league-record $55 million in salary-cap space. It all culminates in a potential splash in free agency designed to make the next four or five seasons for the Heat as productive as the past four seasons.
James, Wade and Bosh are all expected to re-sign longer deals with the Heat, with their recent decisions indicating intent to give Riley an opportunity to land a handful of free agents to stabilize a supporting cast that had grown stale after four straight trips to the Finals and two championships.
Riley often has used baseball clichés to characterize the Heat's lofty plans in these situations. Since he arrived in Miami nearly 20 years ago to work under owner Micky Arison, there have been no fewer than three major makeovers of the Heat's roster that put Miami in championship contention.
The first push landed Alonzo Mourning and Tim Hardaway in the mid-1990s. The second rebuild saw Riley draft Wade, trade for Shaquille O'Neal and surround them with veteran mercenaries in Jason Williams, Antoine Walker, Gary Payton and James Posey to form the 2006 championship team. Then, James and Bosh came in 2010 to join Wade to launch the Heat's current run.
Whereas those roster moves constitute the “swinging for the fences” approach Riley and Arison have taken in the past, that's not what the Heat need right now. They already have hit their home runs with James and Bosh still in the prime of their careers and Wade, 32 and coming off a disappointing effort in the Finals, showing a willingness to buy into the program by opting out with $41.8 million left on his deal.
What the Heat need now is to plug holes to replenish an aging roster that wore down this season and lacked the type of reinforcements that could relieve some of the burden from James and Bosh.
With the ultimate amount of flexibility and financing, the Heat will open free agency aiming for star power. Carmelo Anthony will reportedly meet with the Chicago Bulls first, but he can probably count on Riley at least placing a call to check in and offer a good morning greeting. Kyle Lowry is also likely to be at the top of the Heat's board of free-agent targets.
Those are the stars of the 2014 class.
But there are also plenty of prospects who could add stability to the Heat's roster. Ramon Sessions, Luol Deng, Shawn Marion, Marvin Williams, Marcin Gortat and Trevor Ariza are among the middle-to-lower level free agents who would bolster the Heat's depth and address pressing roster needs.
Riley will have a full menu of options. But much of it wouldn't have been available had James, Wade and Bosh -- along with Heat veteran Udonis Haslem -- not shown the kind of chemistry in recent days that was missing on both ends of the court during that series against the Spurs.
There are also potential dangers involved with free agency. There's nothing stopping a team from poaching the Heat's star players, especially James and Bosh. There are tempting opportunities out there, and you can bet Houston could try to convince either of those players that joining Dwight Howard and James Harden presents a stronger alternative than staying intact in Miami.
But while other marquee free agents are already lining up meetings with potential suitors, there could be a very good reason why there have been no such reports of Miami's free agents taking on recruiters.
Either they're good at keeping their business quiet, or they're in lockstep with one another and Riley.
Entering the offseason, Bosh said the Heat's Big Three are more in tune now than they were in 2010 entering this process.
“It's easier to get on the same page now because we know each other,” Bosh said. “I didn't really know those guys [four years ago]. We weren't like that. We hung around each other, but not really. They did. Now, the communication is so much easier because we can get the kids together, we can go out to dinner with the wives, we can do something. We know how to talk to each other. Those things allow us to connect and feel each other out. Before, it was awkward.”
Now, it has become routine.
James has said the Heat need upgrades at every position on the team. That's not necessarily the case, but his point was clearly made. He's not satisfied with where things stand. Without changes, the four-time MVP isn't convinced his next four years will be as promising as the previous four.
“I just want to win -- it's all that matters to me,” James said. “I've been fortunate enough to play in five Finals. I've lost three of them. That doesn't sit well with me at all, being in this position, being able to get to that point. I take a lot of credit, a lot of blame. I just feel like I could have done more. I'm harder on myself than anyone else could be.”
Riley is now armed with everything he needs to ease that burden.
“We're going to find out what we're made of here,” Riley said recently. “It's not about options. It's not about free agency. It's about what we have built over four years here. We have a chance to [again] do something significant. We have a tremendous opportunity to do something special.”
LeBron has led this team on a remarkable run, as far as it could go under the circumstances.
The Heat's Big Three have turned the reins over to Riley to hit the reset button.