The winner in the NBA-shaking Damian Lillard trade? Pretty much everyone

What a time to be alive – and be Jrue Holiday.

One morning, the sports world is reporting on your hope to retire with the Milwaukee Bucks. A few hours later, you’re a member of the Portland Trail Blazers.

Life moves fast. And in the world of NBA team-building and title-chasing, time waits for no man. Or general manager.

Tuesday’s NBA universe-altering, three-way trade between Milwaukee, Portland and Phoenix – with Damian Lillard becoming a Buck, Holiday and Deandre Ayton moving to Rip City, and Jusuf Nurkić and depth pieces heading to the Suns – offered no better proof of just how quickly entire rosters can turn over in the ever-fluid NBA ecosystem.

And now that the dust has settled, the moves seem to stand as close to a win-win-win as could be drawn up on any ESPN trade generator. That is the beauty of three-team swaps; they are not usually zero sum. Though for one of these three teams, the trade is not without risk.

Let’s examine the deal for each team, starting with the Bucks, the NBA champions in 2021 (which, in light of Holiday heading to the north-west, suddenly feels like a lifetime ago).

For Milwaukee, the prize is obvious: Lillard, named as one of the Top 75 players of all time, probably the best point guard/rapper to ever do it, and a seven-time All-NBA player, coming off a career best 32.2 points, and 7.3 assists per game last season – and now getting a formidable running mate in Giannis Antetokounmpo.

Lillard has proven himself time and again capable of single-handedly winning a playoff series with a single clap (sorry, 2014 Chandler Parsons), ending a short-lived “superteam” (sorry, OKC Paul George) or – my personal favorite – pouring in 55-and-10 (on 24 shots, and only one turnover!) while playing 52 minutes in a 147-140 double OT first-round loss at Denver in 2021.

With the championship-contention-or-bust Bucks on a mission to keep their generational superstar Antetokounmpo satisfied (no matter the beautifully inspirational fodder Giannis offered up after getting bounced from the playoffs) – it is precisely Lillard’s playoff-altering ability that general manager Jon Horst craves in Wisconsin.

After all, simply picturing the Lillard-Giannis high pick-and-roll and/or any dribble-handoff action is enough to make an NBA junkie dream– and conjure nightmares for anyone trying to conceive of a plausible defensive counter. Giannis and Lillard are both, by far, the best player either has ever teamed up with in the NBA – and now they’ll get to chase a championship together, with a Gibraltar-sized chip on Lillard’s shoulder.

It is also now abundantly clear Horst and Co weren’t content to simply take the path of least resistance – perhaps because of Giannis’ recent ponderings to the NY Times about his future – even if that path would have felt entirely understandable to keep trudging. After all, given the Eastern Conference’s uncertainty – here’s looking at you Harden v Morey in Philadelphia, the Kristaps Porzingis experiment in Boston, or the inevitability of Tom Thibodeau running his starting five into the ground in New York – the Bucks deciding to simply run it back with a roster that secured last season’s No 1 seed would have made plenty of sense.

Because make no mistake: trading for Lillard comes with risks.

Those risks include his health (a year on from abdominal surgery), his shaky defense (a contrast with Holiday’s No 2 ranking for guards leaguewide), and last but not least, Lillard’s massive four-year, $206m contract. All of which likely affected Lillard’s trade value this offseason.

In sum, are Milwaukee better positioned with Lillard, for this year at least? Almost certainly – he offers enough playmaking cover to make a deep postseason run possible, even if Khris Middleton’s health concerns linger.

That said, the euphoria of adding Dame may obscure how much the Bucks could miss Holiday’s defensive versatility and strength should Milwaukee end up in a grueling playoff series, where Lillard will undoubtedly be tested and hunted on switches.

Losing Holiday is a gamble – to say nothing of giving up guard Grayson Allen, and plenty of intriguing draft capital – but it is probably a shot Milwaukee needed to take, presumably with Giannis’s blessing.

Meanwhile in Portland, general manager Joe Cronin deserves credit for making the most of a combustible situation (that he of course helped create by drafting Scoot Henderson, a natural replacement for Lillard, at No 3 this summer) and tightroping the build of a new Blazers foundation, without totally alienating his fanbase.

Does Cronin deserve a parade? Probably not. But his bets – in particular, the one on Henderson – all seem sound. After all, a small market team these days almost has to take a flyer on a preternaturally gifted, athletic and grounded 19-year-old like Henderson, given the 14-year disparity (and huge salary difference) between the rookie and Lillard, and their accompanying potential playoff-contending windows.

And in the light of Lillard’s enormous contract, the Blazers did quite well to acquire creatively.

In Ayton, they hope they will get the seven-footer who was the third- or fourth-best player on a team two wins from a championship in 2021 rather than the center who was benched for Jock Landale in last year’s postseason.

Ayton will join what should be a young and super-fun Portland team led by Henderson, the ultra-promising Shaedon Sharpe (who Lillard compared to a young Vince Carter during the Blazers’ long-forgotten hot start in 2022), and the multi-faceted (and slightly underrated) Jerami Grant. Add Holiday to that mix, and it gets even more interesting, although there are reports he may be moved again.

Lastly for Portland, from a value-perspective, adding the 2029 Milwaukee first round pick (alongside 2028 and 2030 pick swaps) is another calculated, and downright Danny Ainge-ian bet, as well.

Meanwhile, Phoenix may feel that much closer to playing for a title again – or at least getting past the defending champion Nuggets in the West – with the 7ft Nurkić in tow to jostle with Nikola Jokić, should the two teams meet again in the playoffs next year.

Throw in the added depth via the suddenly undervalued Allen (40% from three last year) and the lingering wing potential of Nassir Little, and Phoenix did well to turn the inevitable Ayton separation into a more sturdy support system for their three stars, Bradley Beal, Kevin Durant and Devin Booker.

Add it all up, and the trade’s wins are plentiful – with perhaps no bigger winner than the giddy fans who finally got the blockbuster trade they’ve been waiting months for, not to mention the ones who seemingly wrote, produced and directed the preseason climatic ending of the summer soap opera itself: the NBA.