Kawhi Leonard for Damian Lillard. A Sweeping Change Worth the Risk?

The Trail Blazers probably need to make sweeping changes this summer if they ever want to break out of mediocrity during the Damian Lillard era, despite what general manager Neil Olshey claims.

The NBA’s entered into an unprecedented era of blockbuster trades with all-NBA caliber talent like Blake Griffin, Chris Paul, DeMarcus Cousins, Paul George, Jimmy Butler, Carmelo Anthony, Kyrie Irving, and others changing teams in recent years.

Teams are willing to roll the dice on monster trades than ever before! And that’s good news for the Blazers who should be as desperate as a used care salesman at the end of the month to make a deal (assuming they actually, you know, try to do something significant this summer).

The major trade target around the league will be Spurs forward Kawhi Leonard. Leonard missed nearly every game the season with a quadriceps injury, but assuming medical evaluations show no problems, his on-court bona fides will obscure a single season injury history. Leonard’s an unstoppable freak of nature on both ends, one of the top five talents in the entire damn league — finished third in MVP voting last year, and only 26-years old.

Ordinarily he’d be untouchable, but the Spurs have watched their ever-stoic franchise superstar transform into a brooding alleged malingerer, leading to the first public turmoil for a Gregg Popovich team since Avery Johnson tried to start a naked wrestling match in the locker room (Jerome Kersey and Terry Porter cameo appearances).

Even though the Spurs insist everything is fine, Leonard’s refusing to return their calls and may have already requested out of San Antonio.

Could the Blazers Get Kawhi?

Assuming he’s healthy, Leonard fills nearly every need the Blazers have. They’d be foolish not to go after him.

Olshey would likely start with a package centered on CJ McCollum and Zach Collins, which MIGHT work if the Spurs had no other offers, but the reality is several teams are already lining up to top that bid.

For example, the Celtics can offer Jaylen Brown and lottery picks. The 76ers could offer Markelle Fultz, Dario Saric, and lottery picks. The Suns could offer Josh Jackson, Dragan Bender, and lottery picks.

We all love McCollum, but from an outside perspective it’s tough to take on the maximum salary of a 27-year old non-All-star who showed no measurable offensive improvement this season when other teams have blue chip talent on rookie deals AND lottery picks available. There’s a reason the Blazers haven’t been mentioned as a potential destination for Leonard.

What About Lillard for Kawhi?

If the Blazers want to be part of this trade they’ll have to stare down an uncomfortable reality: Do they want to trade Damian Lillard?

The appeal to a Lillard-for-Leonard trade is utilitarian and grounded in Vulcan-level pragmatism. Lillard’s probably at the peak of his powers, likely sneaking onto an All-NBA first team this year, and is immensely popular with several years left on his contract. His trade value will never be higher, creating the rare opportunity to flip a top-15ish player into a top-5 player.

Because of their glut of high-salaried role player and restricted free agents, the Blazers have few other trade options that can create that kind of sure-fire, raw talent improvement. From a pure basketball perspective, this trade is a no-brainer. The intangibles of dealing Lillard, however, may give Olshey pause. It would signal the end of this era of Blazers basketball, and may alienate some fans who have come to adore Lillard.

The Spurs may have intangible concerns of their own with the trade. Lillard and Spurs star LaMarcus Aldridge had a well documented personality conflict as teammates in Portland. It would be incumbent on Popovich to convince the players to put that behind them for the greater good of the team.

Much like the Blazers, the on-court benefits of a trade like this could be enormous for San Antonio and help offset the chemistry concerns. Lillard and Aldrdge have proven on-court synergy and the Spurs already won 47 games this season — this trade could vault them into the 55-win range and make the Spurs a clear third team in the west.

But Kawhi’s Going to be a Free Agent

Other than the lingering quad injury concern, the other drawback is Leonard’s contract. It expires after this season, meaning any team that acquires him is taking a risk that he’ll leave for nothing in a year. If the Blazers did make the Lillard-for-Leonard trade it’s a precursor to a hard rebuild, with an all-time hail mary season thrown in first.

If things actually work out Olshey can (hopefully) convince Leonard to re-up, but if the team falters and Leonard leaves the Blazers can trade McCollum for draft picks, tank the 2019-20 season, and head into that summer with multiple lottery picks and nearly unlimited cap space.

Basically, they’d be gambling a chance of legitimate success in 2019 with Leonard and a subsequent re-signing, for whatever draft assets Lillard would have returned in a more conservative trade.

Bottom Line

Even in the age of the superstar trade, true MVP candidates like Kawhi are rarely available. The Blazers would likely have to part with Lillard to have any real shot at acquiring Leonard, opening them to significant risks and rewards. Olshey will have to weigh whether the clear on-court upgrade is worth the potential fallout if the team doesn’t immediately succeed. For a team that’s taken a maddeningly conservative approach to roster modification, it would be the ultimate sweeping change.