The Truth About Willie Nelson's Legal Troubles

When financial favors were requested of him, Willie Nelson often went above and beyond what was asked. He preferred to enjoy life, and put in his best efforts to ensure those around him enjoyed it too. In response to his attorneys' requests for better financial planning, Nelson simply responded, "It's more fun if we don't" (via Texas Monthly).

Nelson's daughter, Lana, who had a hand in managing her father's finances, estimated that Nelson only kept around 10% of his finances for himself (via Texas Monthly). Nelson was notoriously generous to those around him. For example, former roadie Tim O'Connor was reportedly given a check for $50,000 from Nelson after requesting that he co-sign a loan for the same amount. And Paul English, who played drums for Nelson, held a "Guinness World Record" for the highest paid sideman/drummer, at one time earning 20% of whatever Nelson made (via Saving Country Music).

Though these financial decisions could be considered irresponsible, they are not the sole reason for Nelson's financial troubles. According to Austin360, Nelson claimed his manager from 1975-1978, Neil Reshen, failed to file taxes and made a mess of his finances. Following Reshen's departure (Nelson ultimately sued Reshen for $12.7 million and later settled for an undisclosed sum), he hired accounting firm Price Waterhouse to clean up the mess. This led him to several bad investments in the cattle industry, which Nelson claims cost him $15 million.