in January 2022, Lillard sat across from his old pal and new head coach Chauncey Billups and asked a more pointed question: “What are we doing?”
...
“The biggest message that I wanted to send to Dame,” Billups told me, “was that this thing needs to be built around making sure we bring people around that can actually help him be better.”
...
Billups, in his first year as a head coach, also has had a relationship with Lillard for more than a decade. In 2014, during Billups’s final year in Detroit, the Pistons took a trip West to play Portland. Jared Jeffries told Billups, then near the end of his career, to watch out for the kid from Oakland. “He was like, ‘I got your twin, bro. This dude is your twin,’” Billups said. “Y’all play, y’all act alike. This is your twin.”
...
Billups would send congratulatory texts after big games and offer pointers. When the Blazers lost Game 5 to Denver in the 2019 Western Conference semifinals, falling behind 3-2 in the series, Billups, then a TV analyst, sought out Lillard in an arena hallway. “I saw him in the back and he was like, ‘Hey, man, this is it right here,’” Lillard said. “He almost got at me like, ‘You got to come on with it. Y’all facing elimination.’ I deal best with people that are straight to the point.” Lillard dropped 32 points in Game 6, a Portland win, then overcame a poor shooting night to post a near triple-double on the road in Game 7, sealing the first Western Conference finals berth of his career.
...
But looking forward meant parting with the past. CJ McCollum had been by Lillard’s side every season since his sophomore year, experiencing all the ups and the downs—and the many, many trade rumors.
...
“I think with him and CJ, they’re brothers, and I think they both knew at some point they was going to have to split,” Billups said. “If you wanted more, I was going to try it a different way. They had really pretty much maxed it out, just them two.”
...
Last year, while playing in the Summer Olympics, Lillard was so impressed by Team USA teammate Jerami Grant that he plotted a plan to steal him from the Detroit Pistons.
...
Enamored of Grant’s talent, and aware of his work conundrum, Lillard prepared a blunt pitch. “Bro, if they’re not trying to win and then you decide that you going to leave, tell them to trade you to Portland,” he’d say.
...
Now the starter next to Lillard in the backcourt, Simons signed an extension this offseason that will pay him $100 over four years. A week later, Jusuf Nurkic, another Lillard favorite, signed a four-year pact worth $70 million. With the no. 7 pick in the draft, Portland drafted Shaedon Sharpe, another 19-year-old with immense promise.
“I think we just got to keep building toward winning it all,” Lillard said.
...
Last season was the worst in Lillard’s decade in Portland, but it did give him time to reassess what’s important as he enters the next stretch of his career. When abdominal surgery ended his season last winter, Lillard retreated home and enjoyed a luxury that NBA players rarely experience. “Being at home with my family, my kids, and my wife. Being around my mom, and just going to my nephew’s football games, and traveling, and shit like that,” he said. “Just getting that family time in. I was just able to fill my cup, do the stuff that I never get to do, and just be present with my kids. It just brought me a different type of happiness, and a different type of peace.”
Now, Lillard has everything he could want. It isn’t the typical path for players of Lillard’s caliber in the current climate, but it may be the one that suits him best.
“I love what we have,” he said. “We look really good on paper, the way things stack up. But when you put on the floor you gotta connect, we gotta be tapped in. How well we jell and how connected we are is ultimately gonna show that in our performance.”
