Chauncey Billups just made headlines for an unfortunate reason. On October 23, 2025, the Portland Trail Blazers head coach and Miami Heat guard Terry Rozier were arrested in Florida as part of a federal gambling investigation. The arrests occurred after a game between the Heat and Magic, during which Rozier was in uniform but did not play. According to reports, the investigation involves about two dozen people facing criminal charges across two illegal gambling cases, with ties to organized crime groups. FBI Director Kash Patel was expected to hold a news conference to provide additional details.

But beyond the breaking news, Billups has built an impressive financial legacy over nearly two decades in professional basketball. The former Finals MVP accumulated substantial wealth during his

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