Joe Cronin didn’t just trade Damian Lillard to the Milwaukee Bucks in 2023.
Two years ago, Cronin played the long game. He compiled assets. And he built the Portland Trail Blazers not just with a core for the future, but with a war chest full of trade chips, should a trade war strike during the post-Dame rebuild.
Now, two years into the experiment, the long game is already playing out in Portland’s favor. And as it turns out, Cronin has set himself up to strike when the trade war begins.
Sep. 27, 2023 — On this date, Cronin began the long con.
Portland’s general manager, still very much a greenhorn, traded Lillard, a franchise fixture, after Dame’s trade request. It was the only move after Dame’s gut-wrenching trade request two months prior. But he did so with the future in mind. He compiled assets. He set up the Trail Blazers with both a core for the future and a war chest of trade chips, should a leaguewide trade war strike during the rebuild.
Now, two years into the experiment, the long game is playing out in Portland’s favor, with the Milwaukee Bucks down bad and their future picks looking more and more valuable, a trade war may be on the horizon.
The Latest Giannis Drama
On Wednesday, ESPN’s Brian Windhorst reported that, as it turns out, Giannis Antetokounmpo previously asked for a trade before the 2025-26 season. Shams Charania added that Giannis and his agent are discussing, as of this week, whether his long-term future is in Milwaukee or somewhere else, with clarity expected in the weeks ahead.
The Bucks, 10-13 on the season—and just 1-5 without Giannis—haven’t helped calm the situation.
The team’s play has been tumultuous, and Giannis’ non-contact leg injury on Wednesday only complicates what was already a fever dream of a Wednesday for the Bucks and their fans.
Of course, at this point, no one is reporting that a trade is imminent. That’s important to note.
That said, around the league, these are the kinds of signals that matter. This kind of smoke often leads to flames. And as it turns out, the Blazers are armed with enough fuel to light a fire on the Giannis trade market.
Portland Holds the Keys
From the moment Cronin traded Lillard, the young GM targeted future draft picks that could become extremely valuable. The Trail Blazers’ control of Milwaukee’s 2029 first-round pick, as well as the swap rights in 2028 and 2030, were always a forward-facing bet, and one made against the long-term outlook for the Bucks.
Today, those trade assets are important footnotes in this chapter of Bucks uncertainty. The Blazers hold those picks—not Milwaukee. While the Blazers, almost inexplicably, also roster both Lillard and Jrue Holiday … not Milwaukee.
On the modern trade market, front offices crave future picks from desperate contenders showing cracks. They headline superstar trades for their volatility and major upside.
That’s what happened when Milwaukee sent all those picks Portland’s way, just two years after Giannis and the Bucks won the 2021 NBA Championship. Portland now holds three valuable draft assets, as a result of that contender showing its cracks. And no team will value those picks more than the Bucks themselves, should Giannis force his way out of Milwaukee.
Portland Can Be a Power Broker, Even If Giannis Lands Elsewhere
Milwaukee’s draft picks don’t just give Portland a puncher’s chance at trading for Giannis. More realistically, they give the Blazers a seat at the table—as a facilitator and beneficiary—if a valid sweepstakes emerges.
If a larger market like Los Angeles or New York ultimately wins the bidding, the deal is likely to take on a multi-team structure. Portland’s picks and money-matching salaries then become tools that help complete the framework, and the Blazers can look to take back positive assets,—including extra picks, prospects or rotation players—simply by stepping in to make the math work.
In megadeals, the team that benefits most isn’t always the one landing the superstar, and Portland is built to be that team. It can even do so while keeping some of those Bucks trade picks, which, depending on what Portland would have to trade, might be better than taking on Giannis and his salary anyway.
The Tough Conversation: Portland’s Young Core
Speaking of hypothetical trade packages, the difficult part is deciding what Portland would give up.
Scoot Henderson hasn’t yet made his third-year debut, but hopes are sky high that when healthy, he can perform at a level we haven’t seen—and under the guidance of two future Hall of Famers in Lillard and Jrue Holiday, who are new to the roster.
Shaedon Sharpe, of course, remains the team’s most explosive upside swing. His rim attacks, deep-range pull-ups, and athletic bursts arrive in highlight waves rather than a steady dosage, but the flashes are becoming more consistent. His three-point shooting is the elephant in the room … but I have a feeling fans will look past that when thinking about his trade value at just 22 years old.
Above all else, Deni Avdija’s rise has been the most striking. His playmaking is sharp. His transition game has become a weapon few possess, and his reliable shooting has unlocked a true two-way connector. At 6’9”, he’s become one of Portland’s most reliable lineup stabilizers, which, frankly, is what any team trying to swing a deal with the Blazers would covet. If Giannis is involved, Deni’s name might come up. Of course, that’s not to say he’s on the block. But it’s also not to say he’s untouchable, either.
Cronin’s Long Chess Match Comes Into Focus
The 2023 Lillard trade was about more than resetting the roster. It rebuilt the timeline, expanded the asset base, and allowed Portland to control the very Milwaukee picks that could matter most if the Bucks ever slipped.
That was always part of Cronin’s plan. And two years later, the Bucks are watching their chances of keeping Giannis slip.
Of course, Milwaukee could still stabilize. Giannis could regroup, refocus, and recommitt. But suppose the situation reaches a breaking point. In that case, Portland is one of the only teams positioned to help shape the outcome—either by making a real run at Giannis himself or by extracting value as a third (or fourth) team broker.
If the Giannis Sweepstakes begins in earnest, Portland will be in the room. That’s why the Blazers have quietly become central to every leaguewide hypothetical. They hold the assets that actually affect megadeals.
Cronin didn’t just trade Lillard back in 2023. He set up Portland to matter in any version of the Giannis sweepstakes that was always going to happen down the road.
Whether they’re chasing the prize or helping deliver it, it fittingly falls to Cronin, the GM who put the Trail Blazers in this position with the most significant trade in franchise history just two years ago.
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