How Damian Lillard, the NBA superstar headed to Milwaukee in pursuit of a title, makes and spends his millions

An Oakland, California, native, Lillard did not receive much college recruiting interest out of high school. He decided to play for Weber State — a Division I school in Utah — after the Wildcats' head coach became the first to show serious interest in his talents. He also left with the intention of separating himself from the violence of his home city, which he once told ESPN claimed the lives of many of his friends "before we even graduated from high school."

The 6-foot-2 guard thrived in the NCAA. He earned Big Sky Conference Freshman of the Year honors in his first season on campus, and became one of the most prolific scorers in the country over the next two years.

He opted to skip his senior season at Weber State to declare for the 2012 NBA Draft, where the Portland Trail Blazers selected him with the sixth overall pick. And Lillard wasted no time proving that he was right where he belonged alongside the top talents in the sport.

Lillard got off to a hot start in the NBA, becoming one of just four players to win Rookie of the Year unanimously after he averaged 19 points, 3.1 rebounds, and 6.5 assists per game over the 2012-2013 campaign.

And he only improved from there. Lillard earned All-Star nods in seven of the subsequent 10 seasons thanks in large part to his scoring ability; his seasonal scoring average jumped from around 20 points per game in his first few seasons to 25 a few years later.

By the time he reached his eighth season in the league, Lillard was averaging 30 points per contest, making him one of the most lethal scoring threats across the entire league. But it's not just his mind-boggling point totals that put him on the map.

In the biggest moments, Lillard virtually never disappoints. In fact, he so consistently comes up big "in the clutch" that he earned a special nickname for the superhero-like figure he becomes under the bright lights: "Dame Time."

When Lillard drains a shot in the waning moments of a game — as he so often does — he'll point to the spot on his wrist where he'd wear a watch to signify that he's done it again.

When he was first drafted into the NBA, Lillard signed a four-year, $13,845,166 contract with just over $6.2 million guaranteed. By the time his entry-level contract was up at the end of 2015, Lillard had already established himself as a top-tier talent who could command considerable cash for his abilities.

Ahead of the 2015-2016 season, the point guard inked a rookie extension for five years, $139,888,445 — all of which was guaranteed upon signing. Once that contract expired, he signed a four-year, fully guaranteed veteran's extension worth a whopping $176,265,152.

With an average salary of $44 million per season, Lillard instantly became one of the highest-paid players in the NBA. In all, he's earned upwards of $233 million from his NBA salaries alone, according to Spotrac. And that total doesn't even include income from his ventures off the court.

Lillard signed a multi-year shoe deal with Adidas when he came out of college in 2012. Two years later, when it was becoming apparent he could develop into one of the brightest stars in the NBA, the then-Trail Blazers point guard renegotiated the sponsorship agreement.

The resulting contract was reportedly worth around $100 million for 10 years, amounting to one of the largest shoe deals in NBA history. Lillard's signature shoe, the Adidas Dame, has been popular with fans and fellow basketball players alike, meaning that he's likely due for another big payday come 2024.

Lillard has lucrative endorsement deals with several other brands as well, including Gatorade, Bose, Meta, Modelo, Oakley, Panini, and more. He also co-founded Move, an insole brand made for comfort and performance, and co-owns a Toyota dealership in Oregon.

Lillard has also embarked on a career in music. Dame D.O.L.L.A. has dropped five albums — "The Letter O," "Confirmed," "Big D.O.L.L.A.," "Different On Levels The Lord Allowed," and "Don D.O.L.L.A."

His first album reached No. 119 on the Billboard 200, while "Confirmed" and "Big D.O.L.L.A." each cracked Billboard's Top Album Sales chart. Lillard has also founded his own Indie label called "Front Page Music."

While he's found some success on the music scene, Lillard has earned the vast majority of his wealth through basketball and his related sponsorships. In 2023, Lillard clocked in at No. 25 on Forbes' annual list of highest-paid athletes with a total income of $58.6 million.

All-in-all, the superstar reportedly boasts a net worth that hovers around nine figures. And even though he's publicly acknowledged that it's more than enough to provide for his family for generations, Lillard is still not one to spend frivolously.

In a 2022 interview with Andscape's Marc J. Spears, Lillard admitted that he's "just naturally a worrier" when it comes to finances. He inherited the trait from his father, who always tried not "to do too much" and avoided "being flashy."

"I wanted to make sure that I just was carrying it the right way in the beginning instead of thinking this money was just going to keep coming," Lillard said. "I was more focused on working hard, sticking to what got me here instead of like, 'Oh, I made it. I got it.' And that money, it goes fast."

"I got that management part from my dad."

In the same interview with Spears, Lillard said that "making a lot more money than I ever would've thought" has enabled him to loosen up a bit and spend on "the stuff I like." Clothes and shoes are at the top of the list.

Lillard is regularly spotted donning designer apparel — Balenciaga, Dolce & Gabbana, and Gucci appear to be among his favorites — while walking into NBA arenas or sitting courtside on nights he doesn't play. He's even taken trips to Paris to attend shows during fashion week.

His jewelry doesn't disappoint, either. Though he has an endorsement deal with watch brand Tissot, Lillard's been seen out and about sporting several high-end Rolexes. He often wears gold chains around his neck, too.

Five years into his tenure with the Trail Blazers, Lillard purchased a dazzling estate in the West Linn suburb of Portland for $6.7 million. The lakeside home boasts five bedrooms, 12 bathrooms, an infinity pool, a tennis court that doubles as a basketball court, a gorgeous kitchen with top-end appliances, a home theater, and much more.

Lillard also spent years constructing a custom-made mansion in nearby Tualatin, Oregon.

It's unclear whether he's sold either property in light of his trade to Milwaukee, but he's sure to invest in more real estate now that he's arrived in Wisconsin.

For Lillard, it's all basketball — with a bit of music and parenting sprinkled in — during the NBA season. But once summer comes along, he's free to travel the world and spend quality time with loved ones.

He took a recent trip with family and friends for his 33rd birthday, according to his Instagram account. Activities included jet-skiing, zip-lining, swimming in the pool, and catching some rays on the beach.

And whenever Lillard does splurge on a trip, he flies private. He regularly posts photos of himself and his kids on chartered jets.

Lillard has three kids. His eldest son, Damian Jr., is five years old. His twins, a girl named Kali and a boy named Kalii, will turn 3 in January.

The NBA superstar and the mother of his children, Kay'La Hanson, had been in a relationship since their college days. The pair got married shortly after the birth of their twins in 2021, but sources have reported that Lillard filed for divorce shortly after leaving Portland for Milwaukee.

Lillard has said publicly that he takes pride in being able to provide for his children and alleviate the pressure he and some of his loved ones felt around money as kids. He's also taken on that role for extended family members whenever he can.

"I just don't feel comfortable knowing that I have what I have and then people are just struggling," Lillard told Andscape. "And then when they reach out to you, I feel like it's kind of my job to help them."