Hassan Whiteside Reclamation Project Will Be Damian Lillard's Greatest Test Yet

PORTLAND, Ore. — Fresh off their best season in almost two decades, the Portland Trail Blazers are making big changes.

Blazers president of basketball operations Neil Olshey took an enormous gamble Monday, agreeing to acquire disgruntled center Hassan Whiteside from the Miami Heat as part of a four-team trade that will send Meyers Leonard to South Beach and Maurice Harkless to the Los Angeles Clippers.

The Blazers are betting on their strong culture—and more specifically on Damian Lillard—to make the most of a talented player with plenty of baggage. It's a risk they've taken before, and it's paid off more often than not.

Whiteside will be their biggest test yet.

On paper, trading for Whiteside makes complete sense. Starting center Jusuf Nurkic is still recovering from the leg fracture he suffered in late March. Nurkic's return date is unknown as of now, but he will likely be out until at least the All-Star break, if not longer.

Against all odds, the Blazers got by with Leonard and Enes Kanter in the playoffs to reach the Western Conference Finals. However, that combination wasn't going to be sustainable for a full regular season while Nurkic is out. Whiteside is a more talented player than any stopgap center Portland realistically could have signed in free agency.

The risks with Whiteside are obvious. He hasn't lived up to the giant contract he signed with Miami in 2016, developing a reputation as a stat-hunter whose highlight blocks paper over his weaknesses as a defender. As his role with the Heat diminished, he was open about his frustration with how head coach Erik Spoelstra used him. Combined with some questionable off-court decision-making—in July, Whiteside's $50,000 assault rifle was stolen from his unlocked Rolls-Royce minutes after he purchased it—it helps to explain why his value was so low.

The Blazers are banking on their rock-solid organization and Lillard's leadership to get most out of Whiteside on and off the court. 

There's reason to believe this approach can be successful. After all, it has before.

When the Blazers traded for Nurkic shortly before the 2017 trade deadline, his reputation was likewise at rock bottom. Nikola Jokic's rise into a bona fide star was blocking Nurkic's playing time in Denver, and his obvious unhappiness had become a distraction.

The Nuggets were so determined to move on from Nurkic that they included a first-round pick in the trade with the Blazers, even though he was more talented than center Mason Plumlee, who Portland sent back to Denver in return. But the Blazers saw Nurkic's talent and believed he could thrive in a different environment, that what he could contribute on the floor would overcome whatever concerns there were in the locker room.

That gamble paid off in a big way, as Nurkic resurrected his career and built himself into a legitimate third pillar of the Blazers' starting lineup alongside Lillard and CJ McCollum. That turnaround was thanks in no small part to Lillard, who recognized an opportunity to take Nurkic's career into his own hands. The two forged a bond as close as any in the NBA, with Lillard knowing exactly which buttons to push to make sure Nurkic was as comfortable as he could be in Portland.

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Nurkic was 22 at the time of the trade, still in his third year in the NBA, still trying to prove he deserved a huge payday. Whiteside turned 30 last month and is set to make $27.1 million next season, the final year of a four-year, $98.4 million contract he signed with the Heat in 2016.

Given the way the last two seasons have gone for Whiteside, he has the same opportunity Nurkic did to rewrite his perception around the league and prove he's still a high-level contributor on a team with big-time playoff aspirations.

Olshey has overhauled the Blazers' roster in the early going of the offseason, allowing veteran forward Al-Farouq Aminu to leave for Orlando in free agency and dealing Evan Turner to the Atlanta Hawks for veteran wing Kent Bazemore. Leonard and Harkless, the two players he sent out in the Whiteside deal, had been staples in Portland for years. 

Whiteside is joining a team in transition. The Blazers realized the role players around Lillard and McCollum had likely maximized their potential, but they wanted to take advantage of Kevin Durant's departure from the Golden State Warriors and the suddenly wide-open Western Conference.

The one constant with the Blazers has been and will be Lillard, who kicked off free agency by agreeing to a four-year, $196 million supermax extension (first reported by The Athletic's Shams Charania). Lillard earned that contract not just through his All-NBA-caliber play on the court, but also through his full-on embrace of everything that comes with being the face of a franchise. 

Lillard's teammates swear by him. They talk about how he treats the rookies at the end of the bench the same way he treats his co-stars in the starting unit. He's stood behind head coach Terry Stotts at every turn, and the two have presided over one of the most stable, drama-free locker room cultures in the NBA.

Whiteside will test that culture as much as anything has. But his combination of talent and ability to fill a short-term need makes it obvious why the Blazers think he's worth the considerable risk.

Judging by their track record, it's hard to blame them.

Sean Highkin covers the NBA for Bleacher Report. He is currently based in Portland. Follow him on Twitter at @highkin.