Who Has the Most to Gain in the 2020 Playoffs?

With a true postseason in place, these legacies could receive a major boost in 2020.

The NBA’s restart plan is certainly unorthodox, but given the traditional playoff format ahead, it’s hard to argue that the 2020 champion will be anything but legitimate. The champion will still need to win 16 games, and there will be a true—albeit imperfect—warm-up period before the 2020 postseason. Any talk of an asterisk feels largely disingenuous.

With a true postseason in place, many legacies could receive a major boost in 2020. Kawhi Leonard and LeBron James can both secure a Finals MVP with their third team. James Harden could get the monkey off his back. Even reaching the conference finals should cool talk of a breakup in Philadelphia. The strange circumstances of the playoffs shouldn’t distract from the fascinating on-court action ahead.

So which NBA figures have the most to gain in the 2020 playoffs? We at The Crossover examined the top candidates.

BOSTON, MA - MARCH 6: Jayson Tatum #0 of the Boston Celtics handles the ball against the Utah Jazz on March 6, 2020 at the TD Garden in Boston, Massachusetts :: Brian Babineau/NBAE via Getty Images

Mike D’Antoni

Houston’s head coach entered 2019-20 on the final year of his contract after extension talks stalled between him and the organization, creating a serious sense of urgency at the Toyota Center. Neither D’Antoni nor Daryl Morey entered the year with much job security, and after acquiring Russell Westbrook, Houston has put its chips in the middle. D’Antoni’s job status was a simmering topic of conversation for much of the regular season.

The heat has been turned down a degree in recent weeks. Owner Tilman Fertitta gave a vote of confidence to Morey last week, and effectively noted D’Antoni’s future lies in Morey’s hands. Even an early exit in the 2020 playoffs could still result in D’Antoni getting one more year to reach the Finals in Harden’s prime. Defeating the Lakers or the Clippers in round two could lead to D’Antoni earning a long-term deal that will take him through his early 70s. It’s been an imperfect tenure for D’Antoni in Houston, but it’s hard to argue with the results. He’s gotten the best out of Harden, and he quickly made Westbrook feel comfortable in a new environment. He deserves another shot past 2020 to guide the Rockets to the Finals.

Pat Riley

Pat Riley has nothing to prove at this point in his career. The 75-year-old has tallied five championships as a head coach and two as an executive, standing among the most impactful non-players of the modern era. So what could add to Riley’s Hall-of-Fame legacy? Winning yet another championship in Miami.

Despite the Heat’s impressive 2019-20, their next championship isn’t coming in Orlando. The Heat trend closer to a nice story than a true contender this season, currently holding the No. 4 seed in the Eastern Conference. It’s hard to win a title with Jimmy Butler as the lead option, while Bam Adebayo, Tyler Herro and Duncan Robinson still have plenty to prove on the game’s brightest stage. But a deep playoff run could set the stage for another free-agency coup in 2021.

The 2021 class has been discussed as a potential gold mine for years now, with two obvious options for Miami. There’s (of course) Giannis Antetokounmpo, the crown jewel of the class, and a transformational talent that would immediately vault Miami to the top of the Finals conversation. Then there’s Victor Oladipo. The Pacers guard didn’t look quite like his former self after returning from a knee injury in late January, but when healthy, there’s no denying his immense talent. Pairing Butler with Oladipo could give Miami the top two-way backcourt in the Eastern Conference. Miami could reassert itself as an elite free-agent destination with a deep playoff run in 2020.

NEW YORK, NY - MARCH 6: Danilo Gallinari #8 of the Oklahoma City Thunder drives to the basket against the New York Knicks on March 6, 2020 at Madison Square Garden in New York City, New York :: Jesse D. Garrabrant/NBAE via Getty Images

Danilo Gallinari

Perhaps the 2020 free-agent class lacks the sizzle of the 2021 crop, but there are still quality players available on the market for a slate of title contenders. Consider Danilo Gallinari as one of the top options.

Gallinari doesn’t jump off the page at first glance. The Italian forward has never made an All-Star team, never averaged 20 points per game, and he sports a lengthy injury history. Galinari won’t receive a nine-figure deal at this point in his career, though with a strong playoffs, he could cash in with a hefty multi-year contract.

The 6’10” forward appears to be aging like a fine Chardonnay as he approaches his age-32 season. Gallinari has averaged over 18 points per game in four of the last five seasons, and he’s crossed 40% from three in each of the last two years. He’s a legitimate 6’10” with a smooth release, and he’s more agile off the bounce than one would expect. Gallinari may be a defensive liability, but the right scheme can hide even the most egregious wing defenders. Expect a playoff team (perhaps even Oklahoma City) to shell out major dollars if Gallinari continues his impressive season.

Jayson Tatum

Boston’s precocious wing is already creeping toward top-10 status across the league, and he’s likely to garner multiple All-NBA selections over the next decade. Tatum is a singular scoring talent, one who has refined his shot chart in 2019-20 after avoiding contact at the rim far too often in 2018-19. The Duke product is surely one of the game’s top assets entering the 2020 playoffs. But a surprise playoff run could kickstart a true superstar ascent.

Tatum could zoom past the likes of Paul George and Anthony Davis among the league’s top players if he leads the Celtics to a championship—or at least the Finals—and he very well could be positioned as the premier Boston athlete of the 2020s. Tom Brady is in Tampa. Mookie Betts is in Los Angeles. Perhaps this is more an honorary designation, but it could lend to the legend of Tatum growing exponentially over the next decade. Let’s not enshrine Tatum in Springfield just yet. But if Boston wins the East, he could be well on his way to a Hall-of-Fame plaque.

HOUSTON, TX - MARCH 10: Russell Westbrook #0 of the Houston Rockets dunks the ball against the Minnesota Timberwolves on March 10, 2020 at the Toyota Center in Houston, Texas :: Bill Baptist/NBAE via Getty Images

Russell Westbrook

Russell Westbrook was never going to win a ring as a leading man during the Thunder’s peak in the 2010s. That’s no disrespect to the 2016-17 MVP, but Kevin Durant wasn’t a second fiddle in Oklahoma City nor Golden State. Now in Houston, Westbrook finds himself in the same situation, this time behind James Harden in the offensive hierarchy. But that doesn’t mean there isn’t plenty of upside for Westbrook’s legacy in the 2020 playoffs. A championship in Houston could put Westbrook among the greatest No. 2 options in NBA history.

If the last two months of the season were any indication, Westbrook should be in prime position to push the Rockets to a potential second-round upset against the Lakers or Clippers. He’s averaging 31.7 points and 6.8 assists per game since the calendar turned to 2020, shooting a blistering 52.7% mark from the field. Perhaps Westbrook is a dip below his athletic peak at this point, but he was playing perhaps the most efficient basketball of his career before the COVID-19 hiatus. Westbrook has attempted more than two three-pointers in just four of his last 20 games. He’s driving to the rim with abandon, punishing teams who choose to double James Harden. After a rocky start, Harden and Westbrook found their groove around February.

Houston has made the best of its situation, making an imperfect fit work amid a roster with noted deficiencies. The Rockets were on pace for their fourth straight 50-win season in 2019-20, and Harden will likely finish in the top three of the MVP voting once again this season. In most years, Houston would be among the championship favorites. But in 2020 the Rockets face an uphill road. The Finals are a serious long shot for Houston, though both Los Angeles teams should be on upset alert. For the Rockets to move past the second round, Westbrook will need to be elite. An MVP-level playoffs could shift the narrative on his Hall-of-Fame career.