Pat Riley continues to toe the thin line between winning and misery

Pat Riley's all-or-nothing approach may have caught up with him this summer, losing Dwyane Wade and adding few reinforcements.

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It’s been a long summer for Pat Riley.

Between the Heat’s public divorce with Dwyane Wade, their organizational struggle with Chris Bosh and the ongoing attempts to field a competitive roster—which culminated in the signing of Dion Waiters on a team–friendly deal Monday—the NBA’s master planner has been more reactive than active this off-season.

It was Riley who set himself up for high expectations this summer, when he told reporters at his end-of-the-year press conference that June and July would be fun and fruitful. Instead, they were hurtful and barren.

Wade fled to Chicago, at least momentarily fracturing the goodwill of a fan base that worships Riley. Who was right? Wade was understandably insulted Miami never made him a top priority after 13 years with the franchise. But Riley also offered the 34-year-old guard more than $40 million.

And what about Bosh? The Heat’s big man wants to play, but the organization is uncomfortable watching him take the court while still on blood thinners. Bosh is trying to convince the Heat to let him play under a new medication that would exit his system before games, while the team is reluctant to entertain such dangerous scenarios—all while Bosh’s massive salary cap hold hangs in the balance.

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How did Riley, whose hair seemingly hasn’t moved out of place since 1980s and who can’t break a sweat in an Armani suit under the South Florida sun, find himself so frazzled amid so much chaos? (And if you think Riley isn’t in a weird emotional state, you only need to read his text to Dan Le Batard after losing Dwyane Wade.)

It looks like Riley’s all-or-nothing attitude has finally caught up to him.

Alexander Tamargo/Getty Images

It’s heresy (and hurtful) as a South Florida expat to suggest Riley’s mastermind ability is slightly overrated, but that’s exactly what I’m about to do. Riley swung a trade for Shaq, but within three seasons had a largely dysfunctional roster. Riley signed LeBron, but is it Wade who deserves credit for luring James to Miami? And while Riley held out for James, he largely wasted arguably the two best years of Wade’s career. And since James has left, so too has Wade and any immediate hopes of challenging in the East.

The thing is, any move Riley makes can immediately be couched in what makes his cult so powerful: a chance at a bigger move in the future.

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That’s really the only way to describe the Heat’s off-season this year, it’s all about creating a chance at a bigger move in the future. Miami’s rash of recent signings—Luke Babbitt, James Johnson, Willie Reed, Wayne Ellington, Waiters—were all about maintaining cap flexibility in 2017, when Russell Westbrook, Blake Griffin and other big names will likely be free agents.

Miami can create a significant amount of cap space next summer if they trade Goran Dragic, and will have a Micky Arison-yachtload of room if Bosh doesn’t play again. You can 1,000% believe Riley has already begun going through these machinations, plotting a big splash that could be the final masterstroke for the 71-year-old.

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There is certainly nothing wrong with playing for the home run, unless you’re doing it like Sam Hinkie. But it’s that catch-a-whale mentality that ultimately led Riley to lose Wade, refusing to offer the franchise’s most beloved athlete a third year so he could keep cap flexibility.

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Of course, Riley’s had plans before, many of which were blown up when LeBron decided to leave in 2014, leaving the Heat grasping. The Heat are in the unique position of having experienced the best and worst sides of NBA’s players-wielding-power era.

But these are the stakes when championships are the singular focus, as they are for Riley. When you hit, the NBA Finals are coming through Miami every year and your city becomes the center of the basketball universe. When you miss, James Johnson and Derrick Williams are battling for starting forward spots while Udonis Haslem will be expected to look after your max-contract center.

There’s winning and then there’s misery. That’s one of Riley’s core philosophical tenets. This summer has been miserable for Riley, and so will this upcoming season. But if there’s winning at the end of the tunnel—perhaps a couple more stars really do decide to team up in Miami next summer—it will have all been worth it. Again.