MIAMI -- Pat Riley had already executed the greatest coup in the history of NBA free agency, but his maneuvering was far from finished.

The Miami Heat president had locked up LeBron James, the league's premier player, as the centerpiece of a star-studded haul that included the addition of Chris Bosh and the re-signing of Dwyane Wade. But on one of James' first nights in South Florida in the summer of 2010, the superstar was struggling with the emotional departure from his home state of Ohio while his now-wife, Savannah, was anxious about their family's transition. On top of everything else, the couple was starving. Savannah craved Italian.

LeBron settled into his normal role as facilitator. And with one phone call, Riley switched from franchise cornerstone to James family concierge.

"It was a place out in Coral Gables," James said this week. "I made one call to him. He made one call, and everything was set up before we got in there. Everything was taken care of. They gave us the back room of the restaurant and everything. It was spectacular. And Savannah got what she wanted."

James then laughed and shook his head in disbelief.

"Obviously, the game of basketball is what's most important," James said. "But the family side is just as important, because if the family isn't secured then it affects everything else. [Riley] wants to win more than anything. But he cares about how your family and your kids and the people around you are doing. And that's huge, especially in this business. When you're here, you feel that."

That family-friendly approach and personal touch have helped Riley to execute blockbuster player acquisitions and build championship contenders for parts of three decades. But with potential luxury-tax penalties looming, and James, Wade and Bosh all able to opt out of their contracts after this season, Riley faces perhaps the biggest challenge of his front-office career to keep his surrogate Heat family intact.

LeBron James and Pat Riley have a good thing in Miami. Will salary-cap realities get in the way? Ron T. Ennis/Fort Worth Star-Telegram/Getty

According to the ESPN Forecast panel, the Heat rank second behind the San Antonio Spurs in a rating that gauges the success, stability and decision-making of a franchise's ownership, front office and coaching staff. The Heat's management (president/GMs) also ranks second, behind the Spurs.

Riley's résumé, as a Hall of Fame coach and executive, along with his reputation one of the league's most respected -- and shrewd -- businessmen in the game, have made him as polarizing as he is successful. But his methods and high-risk gambles have frequently produced championship results -- seven, to be exact -- from his days coaching the Showtime Lakers and overseeing major overhauls of the Heat's roster. But even Riley, who once compared himself during trade talks to a riverboat gambler, has concerns about the uncertainty that looms after this season.

"You always fear," Riley told ESPN.com. "It's not a real fear. I always have concern when players are in the situation they're in. But we feel we have the best organization in the league for those players to stay, and to also attract others to want to come here. With our three guys, we hope that this turns into a generational team. And that it's not just we're at the end of this four-year run right now because players have some options this summer."

The Heat have endured a wild ride with their current roster. James has fallen slightly off his MVP pace from previous seasons and Wade has missed 23 games this season, primarily as a cautionary measure to protect his balky knees. There have been 19 different starting lineups and the team still doesn't have a strong feel for what offseason acquisitions Michael Beasley or Greg Oden might provide in the playoffs. And Miami is relying heavily on veterans in their mid-to-late 30s -- Ray Allen, Shane Battier and Chris Andersen -- to bolster the bench.

Yet the Heat have pushed through it all, moving into first place in the East with nine games left in the regular season.

Riley's confidence in his roster has withstood some frustrating and inconsistent stretches this season. The Heat president started his career coaching Magic Johnson, Kareem Abdul-Jabbar and James Worthy to four titles over the span of nearly a decade in the 1980s. Now Riley, who turned 69 last month, has visions of a perfect bookend to his decorated career.

The goal is to retool the Heat's roster around James, Wade and Bosh to keep them together and in title contention for another handful of years and produce another dynastic decade. Despite difficult financial decisions looming amid a more punitive luxury tax set to kick in this offseason, Riley hopes to rely on three franchise pillars that have kept the Heat proactive and productive all these years. It starts with stability.

Riley believes he still works for a team owner in Micky Arison who remains as committed to winning and producing an elite product now as he was when they first met 19 years ago. Securing James in 2010 was the most recent splash, but Riley points out that Arison has been willing to create waves for decades. The process began in 1995 when, just two months after Riley was hired, Arison signed off on a trade that brought in Alonzo Mourning and later led to deals for P.J. Brown, Juwan Howard, Tim Hardaway and Dan Majerle. Riley said what the Heat pulled off in the summer of 2010 was similar to what they initially had visions of doing over a nine-month span in the mid-1990s before the NBA voided Howard's contract.