After trading for Damian Lillard, the Blazers started shopping Jrue Holiday to contenders.

In a huge, league-changing trade, Damian Lillard will join the Milwaukee Bucks, giving Giannis Antetokounmpo the best point guard he has ever played with and putting Lillard on the best team he has ever played for.

To the Portland Trail Blazers in exchange, the Bucks are sending a first-round pick in the unprotected class of 2029, two pick swaps, and Jrue Holiday, while Grayson Allen goes to Phoenix.
From the Blazers’ point of view, the Milwaukee future first plus trading Jusuf Nurkic for Deandre Ayton was a better offer than anything Miami could have made.
However, it also enables them to keep looking for more future assets by shopping Holiday to other contenders, as Adrian Wojnarowski claims they plan to do.

Holiday is regarded as the NBA’s best perimeter defender and will be very valuable to teams that want to compete.
Holiday should bring in at least another first round pick for any playoff contender looking to add a point guard, including the Miami Heat.
Since it would be much simpler to move Holiday to a fourth team as part of one trade than deal him separately, we’ll probably have to wait until the Holiday portion of this deal is completed before it’s officially announced.
However, it’s still unclear where Holiday will actually go.

It’s challenging to predict who will be the leading candidate for Holiday because you can convince yourself that he makes sense in a lot of situations.
He’s the kind of point guard who can fit in alongside an established point guard as well, providing a strong defensive presence and secondary ball-handler to relieve pressure off of another star guard.
All the teams in the Lillard sweepstakes still figure to want a point guard upgrade.