Lowe: A Dame-Giannis pick-and-roll! Did Miami play it too cool? Breaking down this colossal Lillard trade

When Giannis Antetokounmpo put the Milwaukee Bucks and the league on notice — twice — the Bucks had no choice but to explore what role player upgrade they might get for the only first-round pick (its 2029 selection) it could trade outright.

The challenge in such an incremental move would be finding a player who would nudge the needle enough to surrender that pick with light protections, plus the needed matching salaries — likely those of Grayson Allen and Pat Connaughton, presuming the Bucks would not break up their championship core.

Skeptics within the league wondered: Why burn that pick in an inconsequential move when the Bucks could wait until this offseason and bundle more picks in a game-changing trade?

The reality is that the Bucks did not have that time nor the luxury of waiting to see this season play out and failing again (and, yes, last season was a failure.) The risk of Antetokounmpo requesting a trade would be too great. Potential suitors were already gearing up.

And so in an NBA earthquake, the Bucks dispensed with the incremental moves and reached for an improbable blockbuster: swapping Jrue Holiday, the two-time All-Star they acquired the last time Antetokounmpo’s future in Milwaukee appeared uncertain, that 2029 pick, and two unprotected first-round picks swaps (2028 and 2030) to the Portland Trail Blazers for Damian Lillard — the main part of a three-team (for now) megatrade that also sent Deandre Ayton to the Blazers, with Jusuf Nurkic and role players from both Milwaukee (Allen) and Portland (Nassir Little) headed to the also-all-the-way-in Phoenix Suns.

It is a trade that both keeps Lillard away from East rivals — notably the Miami Heat, Lillard’s top choice — and deals at least a partial blow to teams hoarding assets for any future Antetokounmpo pursuit. One of those teams may end up nabbing Holiday as a consolation prize, though his market will be very wide, league sources said Wednesday. With Lillard, the Bucks reassert themselves as favorites in the East.

Milwaukee is trading two starters for one, and one of the league’s best perimeter defenders in Holiday for a minus at the point of attack in Lillard. Connaughton seems the best candidate to slide into Allen’s fifth starter role. Connaughton is stouter than Allen on defense, but the Bucks no longer have a bonafide wing “stopper” type to guard Jayson Tatum, Jaylen Brown, Jimmy Butler, and the other elite wings in the East. (Butler just cackled reading that sentence given the meanness he unleashed on Holiday in the playoffs — even if Butler’s Heat could enter the Holiday derby, per league sources.)