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Five Country Singers That Almost Lost It All..

Updated: Apr 25

Some of our all-time faves have lived to tell as we like to say. Naturally, the artists that come immediately to mind are Hank Williams, Willie Nelson, and Dottie West among others. But we wanted to explore some not so typical examples of financial loss among some of our favorite country singers, and how they made it through.

The reasons for financial loss In many instances is a combination of trusting the wrong people, not staying on top of financial matters, substance abuse problems and even natural disasters. Some of these stories are heartbreakingly sad, but fortunately for most there was a light at the end of the tunnel. Thankfully that light wasn't coming from a steam rollin' train. :)



The greatest country singer of all-time and my personal favorite.

The Possum was no stranger to heart-breaking times, and unfortunate events explored previously in this blog. Unfortunately, post Tammy Wynette, and pre Nancy era George had developed a severe alcohol and cocaine addiction. His music suffered as noted with only two songs topping the charts as a solo artist in the 1970s. His substance abuse problems also kept George from performing at scheduled concerts.

The infamous "No Show Jones" moniker was unfairly attached to George. In his book "I Lived To Tell It All" George shared how some venues would advertise he was going to play at a certain date when he was already scheduled somewhere else just to opportunistically pad their pockets at his expense.

The life of excess came to a head in 1978. Promoters were suing George for missed concert dates. He had $36K in back child support an arrest warrant, and 1 million plus in debt. With record sales waning, and debts mounting George filed for bankruptcy. The following week he added an assault charge to his resume of unfortunate events.

The following year was even worse for Jones. He was homeless, and living in his car. Willie Nelson, and friends came to his rescue by recording My Very Special Guests. The revenues from the album helped, but it would take several years, more arrests, and an on, and off again toxic relationship with alcohol before beating that devil. George would eventually kick cocaine, which was easy for him, quit alcohol, and regain not only his riches, but his life, and most importantly his peace of mind. It was a long climb back up, but he made it!

Artist: George Jones

Song: These Days I Barely Get By

Album: The Best of George Jones

Single Billboard Debut: 3/22/1975



Merle Haggard
The Hag

The Mighty Merle is one of the very few that can give George Jones a run for his money in the singing category. It's hard to believe that we may have never been delighted by Merle's iconic sound, if he had made just one wrong decision while in a California prison.

What I am specifically talking about is when he was pulling his fifteen year stint in San Quentin, his cellmate Rabbit Kendrick planned an escape, and wanted Merle to go with him. In the last hours before the planned prison break Merle decided not to go. The Hag may not have known it at the time, but it was a fateful decision that could have changed the course of his life forever. Rabbit ended up killing a police officer, and was captured. A year after Merle was released early for model citizenship, Rabbit was executed..

Though Merle was a habitual offender since his youth, he was not a hardened criminal. It is easy to discern Merle's soft heart when you read the lyrics to some of the songs he wrote. As a matter of fact it wasn't crime, drugs or alcohol that precipitated the loss of his fortune. It was making the wrong decisions in business, and in love.

Merle was married five times and fathered six children. His child, and spousal support payments rivaled that of Hollywood stars in the 90s.

He also had several lawsuits for copyright infringement while alive, and after death as many unlawfully sought to profit from his talent without paying royalties to the artist. Some of the companies sued were the Smith Music Group, Green Train, and a quasi fan who stole a cassette of unreleased music from Merle's tour bus, and then tried to sell it on Ebay for $325,000!

Unfortunately, Merle was not immune to lawsuits as he was also sued for canceling show dates. 600 of Merle's songs were sold for 3 Million to help offset his 14 Million dollar debt which also included a 5 Million debt owed to the IRS.. But in true Merle fashion he kept working, and performed weeks before his passing. He was in such fragile health that Toby Keith, who was onsite stepped in to finish Merle's last show at the Mandalay Bay Casino in Las Vegas.

Artist: Merle Haggard

Song: The Bottle Let Me Down

Album: Swinging Doors

Single Billboard Debut: 8/27/1966



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New Traditionalist Randy Travis

For fans of old school country Randy Travis was a hero! Randy was instrumental in bringing traditional country back in the 80s & 90s along with Alan Jackson, George Strait, Dwight Yoakam and several others. It seemed as if everything Randy recorded topped the charts. With 23 number ones, 6 Grammy wins, and a multitude of ACM & CMA awards among many others, Randy was unstoppable.

The troubled youth who had turned to drugs, and alcohol at the age of eleven was finally hitting his stride in Nashville. At one point Randy's fortune was estimated at 36 Million. One of the key players in Randy's career was Lib Hatcher, who owned a bar in Randy's hometown w/ her then husband.

Of course as the story goes she divorced her husband and moved to Nashville with Randy. They eventually married in 1991. All the business aspects of his career were managed by Libby. Randy shares in his memoir how he was under the impression that his voice was insured by Lloyd's of London, and that there were investments, and money in the bank.

Libby filed for divorce after 19 years of marriage. During their divorce proceedings it became clear that most of the shared assets were gone.. Randy had to start all over again as even the royalties that he should have received were annihilated due to advances that were taken unknown to him. There were also lawsuits, and counter lawsuits stemming from the divorce where it seemed like the only parties truly benefitting were the lawyers. His near fatal 2013 stroke exacerbated an already complicated situation.

Randy pulled through personally, and financially, and is in a much better place now. He streamlined his life by selling his condo, and a Santa Fe Ranch. He relearned how to walk, talk, and has gained enough strength to tour with the help of singers, and musicians to augment the shows. An induction into the Country Music Hall of Fame cemented his legacy in 2016.

Artist: Randy Travis

Song: On The Other Hand

Album: Storms of Life

Single Billboard Debut: 8/31/1985



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Twitty Burgers

Very few artists can claim the career trajectory of Conway Twitty.

His career spanned five decades with pop, and country chart toppers. Conway started out in high school baseball, and was signed by the Philadelphia Phillies, but unfortunately was drafted into the U.S. Army before he started with the championship team.

But Conway would parlay that same determination, and perseverance into a music career where he topped the charts an unprecedented 41 times! That also includes the number one pop hit "It's Only Make Believe" in 1958.

Conway was also a shrewd business man and spearheaded several ventures unfortunately not all were successful. Case in point,

Twitty Burgers, a chain of fast food eateries that featured a burger with a deep fried graham cracker crusted pineapple, cheese, bacon and a beef patty!! Dear God lol... He generated a lot of financial help from his friends about 75 or so invested in the venture including Merle Haggard, and Harlan Howard. After a year or so the eatery went belly up.

One of the recurring pieces of advice I always read in Forbes, and Entrepreneur Magazine is to identify your potential audience by conducting some research before launching a business. Conway tried to sell the idea to other established restaurant chains, but there were no takers, and that may have been a good warning to heed. But since it was a burger he had fond childhood memories about, he wanted to share the food joy with others which is totally understandable, and a compelling reason to get the wheels turning..

In business though, your brain has to override your heart. Not all ideas are great ones even, if your heart says so. Conway also did not know much about the restaurant business, and it did not look like there was a written business plan which is key to the success of most enterprises. A business plan tells you where your idea/business is currently at, and where you want it to go, and most importantly how you are going to get there. Here is a great example.

Twitty Burgers went bankrupt with a total of zero assets.

But something very interesting did happen with the demise of the venture. Conway being the standup gentleman that he was paid back all the investors with his own money, and wrote the expense off when he filed his taxes. The IRS challenged a portion of the write-offs, and Twitty had to take them to court! I think the Tax Court Judges were country music fans because Conway won, and the historic ruling was never contested.

Artist: Conway Twitty

Song: I Couldn't See You Leavin'

Album: Crazy In Love

Single Billboard Debut: 1/5/1991



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Kenny Chesney

I have serious doubts about anyone who doesn't vibe with Kenny Chesney's beach country sound. So laidback, and easy breezy, just like the late Jimmy Buffet, but with more twang. Kenny has been on top of the country music game for 20+ years now. His tours are always among the top grossing in any music genre!

Kenny has topped the Hot Country Song chart twenty three times, and counting. AND has won the CMA Entertainer of the Year four times. All of his success has made it possible for Mr. Chesney to live the type of life many just dream about. His songs about your toes in the sand and a drink in your hand are not just lyrics, it is a lifestyle.

Kenny spends much of his time as an islander living coastal in the U.S. Virgin Islands where the lyrics to some of his most iconic tunes come to life. Unfortunately, as I know too well living coastal in Florida, hurricanes are an equal opportunity destroyer. in 2017, the disastrous Hurricane Irma leveled Kenny's house in St. John.

He said it was a biblical level devastation he had never seen before. In my home state, 77 people were killed. Kenny responded by launching the Love For Love City Foundation, and donating revenues from some of his music to help with recovery, and rebuilding efforts.

Artist: Kenny Chesney & Uncle Cracker

Song: When The Sun Goes Down

Album: When The Sun Goes Down

Single Billboard Debut: 2/7/2004


If you walk away with a lesson from this particular blog post let it be to

choose wisely, base your decisions on facts. In the event that you are starting a business or going into business with others, you have the right to see the business plan, and financials. A business attorney, and CPA can help you exponentially as you move forward. Doing these things in the beginning can save you a lot of headaches later.

As read even the most dire and catastrophic situations can offer a sliver of hope, and an opportunity to turn tragedy into a victory by the lessons learned, and helping others. Regardless of the situation, always try to keep your spirits high, and keep faith, and hope alive.

Have a great rest of your day.


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