Biography & Early Wealth Journey

With a lengthy road to recovery ahead of him, Lillard was waived by the Bucks. Milwaukee did that in order to sign center Myles Turner, who had just reached the NBA Finals with the Indiana Pacers. But the Bucks still owe Lillard the money remaining on his contract—which is worth about $112.5 million.

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Now, the Bucks will pay Lillard $22.5 million per season through 2029. That makes him the third highest-paid player on Milwaukee's books for the upcoming season, even though he's been off the team for over a year.

Primary Income Streams & Multi-Million Contracts

Only Tyler Herro ($33 million) and Turner ($26.5 million) will be making more than Lillard during the 2026-27 campaign. The next closest players are Kyle Kuzma—$20.4 million and provider of sage financial wisdom—and Gary Trent Jr., who just signed a $64 million deal that the NBA is investigating for circumventing league rules.

Meanwhile, Lillard, who missed the entirety of last season as he recovered from his injury, is also getting paid by the Trail Blazers. He signed a three-year, $41 million contract to return to Portland after the Bucks waived him, so he's due for an additional $13.3 million from the Trail Blazers.

Nearly $39 million from two teams with over a calendar year in between games? Rehabbing an Achilles injury is a brutal process with a tough emotional toll, but at least Lillard is getting some relief in the form of a massive payday—one the Bucks will likely rue for the rest of the decade.