The Truth About Willie Nelson's Legal Troubles

Born in 1933 in Fort Worth, Texas, Willie Nelson began his journey to country superstardom at an early age. Nelson's grandfather taught him how to play guitar as a young boy. By the early '60s he'd find himself playing in Ray Price's band in Nashville, and by 1975 his first major album, "Red Headed Stranger," which featured the hit song "Blue Eyes Crying In The Rain," began playing from record players and radios across the country (via Britannica). He spearheaded the outlaw country movement and released countless hits throughout the following decades, cementing his position as a country legend.

With such success, you might think that Nelson found himself amassing the sort of wealth most people will never see in their lifetime. For Willie Nelson, this simply wasn't the case. While there was always a steady stream of money coming into the Nelson estate, it tended to enter through a revolving door, with Nelson spending it as quickly as it came in on both himself and those in his circle needed a helping hand.

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.

After years of generosity and financial missteps, the walls of Willie Nelson's financial state began closing in on him. With a $16.7 million tab for unpaid back taxes, Nelson's assets were seized by the IRS on November 9, 1990, in the form of clothing, equipment, his gold and platinum records, and more (via Rolling Stone). One asset he was determined to keep out of the IRS' hands was his guitar, "Trigger."

Trigger has been with Nelson since the early days of his career. He has even been quoted as saying, "When Trigger goes, I'll quit" (via Texas Monthly). When his home in Tennessee caught fire in 1969, it was one of the only things he rescued from the flames. In the Rolling Stone documentary "Mastering the Craft," Nelson recalls the events of that night and says, "I came home, rushed in, and I went in and got my guitar and a pound of weed. I saved Trigger, so it was a good day." Having battled a house fire to keep Trigger safe, Nelson wasn't about to give the instrument up. He'd heard about the IRS seizing musician's instruments for auction in the past, so he entrusted his daughter, Lana, with bringing Trigger from his studio directly to his home in Hawaii. To this day, Nelson is still making music with Trigger.

Following the initial seizure of assets, Willie Nelson spent two days in meetings and negotiations with IRS agents and managed to whittle down his debt to $9 million (via Rolling Stone). During that time, he could be seen parking his bus outside the office and signing autographs for fans, including some of the IRS agents with whom he was meeting. Following the negotiations, Nelson released an album commemorating the event to raise the funds to pay his debt, aptly titled The IRS Tapes: Who'll Buy My Memories. According to Rolling Stone, the album did not sell as well as Nelson had hoped — due in part to Nelson advertising the incorrect purchasing phone number on a T-shirt.

After appearing in commercials to boost his financial state, Nelson was able to pay down his debt. Throughout the ordeal, Nelson maintained a positive attitude, telling Rolling Stone in 1995, "Mentally it was a breeze. They didn't bother me, they didn't come out and confiscate anything other than that first day, and they didn't show up at every gig and demand money. I appreciated that. And we teamed up and put out a record." 

These days, Nelson has a net worth of $25 million, according to Celebrity Net Worth. But it seems as long as he still has Trigger, there's not much more he needs. "As long as I've got my guitar, I'll be fine" Willie often says (via Texas Monthly).