Trail Blazers stick it to Damian Lillard with Jrue Holiday trade

Lillard asked out in Portland because he wanted to play for a contender. Specifically, he wanted to play for the Eastern Conference champion Heat. But Lillard's agent, Aaron Goodwin, annoyed the Blazers by allegedly calling non-Miami teams to warn them against trading for his client. Portland didn't communicate with Miami for months and ended up trading the perennial All-Star to Milwaukee, perhaps the polar opposite of Miami as a city.

Days later, the Blazers turned around and traded Jrue Holiday, who came over in the Lillard deal, to the Boston Celtics. That's Milwaukee's biggest rival in the Eastern Conference (no offense to the Heat). Not only that, but Holiday was defending Lillard when he had the worst playoff series of his career in a first-round sweep by the New Orleans Pelicans in 2018.

Holiday held Lillard to 35.2 percent shooting from the floor and 30 percent from behind the arc, and he hounded Lillard into 16 turnovers in four games. Meanwhile Holiday went for 27.8 points per game and 6.5 assists in the series.

It's not that Portland was malicious. The Blazers got a great return from the trade, getting two first-round picks, young center Robert Williams and veteran point guard Malcolm Brogdon in the deal for Holiday. Now they're planning to trade Brogdon for more assets.

But it has to sting Lillard. After years of struggling to contend in Portland, he joined the Bucks and became the championship favorite. A few days later, Lillard's path to a title got much tougher. If Portland turns around and sends Brogdon to Miami, it's going to look personal.