It will be easy to criticize my presumptuousness in this blog because I’m going to compare myself, in a way, to Kris Kristofferson, an actor/singer/songwriter we lost last year. Kristofferson won numerous Country Music Association awards and Grammys, along with a Golden Globe award and an Academy Award nomination. He also received several other “minor” awards that far outshone anything I’ve received. While I’ve had a relatively successful career, Kristofferson’s has dwarfed mine. Plus, most women found him gorgeous, and I haven’t been cursed with that affliction.

With that said, I recently came across on YouTube a four-part series on Kristofferson, hosted by Steve Earle in 2008, and found many similarities between Kris’s life and mine. So, forgive my presumptuousness if you can and hear me out.

Kris wrote hundreds of songs, but four of his biggest hits were recorded in a few months in the early 70s — “Sunday Morning Coming Down,” recorded by Johnny Cash, “For the Good Times,” recorded by Ray Price, “Me and Bobby McGee,” first recorded by Roger Miller but Janis Joplin posthumously made it a huge success, and “Help Me Make it Through the Night,” originally released by Sammi Smith and later by more than 400 other artists. While Kris lived more than a half-century more, having success in a variety of ways, that brief early-70s period gave him enough continued royalties that he didn’t have to work any longer if he didn’t want to.

For me, my most successful moment was a six-month period in 2000-2001 when I was able to net more than $1 million. I chronicled this run in my “Million Dollar Video Poker” autobiography. While the money was enough for me to retire, if I wanted, it gave my career the boost of credibility. I was essentially the same player before and after the million-dollar experience, but many players took winning that much as a sign I was very knowledgeable. And they bought my products.

While Kris’s run was a lot more lucrative than mine, probably the biggest difference between the runs was the percentage of luck versus the percentage of skill. While both of us had a healthy dose of both skill and luck, luck is a much bigger factor in gambling success than it is in writing four critically acclaimed and commercially successful songs back-to-back-to-back-to-back.
During and after Kris’s success in the 70s, drinking, drugs, and womanizing cost him his marriage to Rita Coolidge. My closest parallel to that also happened in the 70s — which was well before I moved to Vegas and experienced gambling success. While I was never a heavy drinker, and dabbling with marijuana was never a major hobby, there was a period of almost ten years when I couldn’t be trusted to be a faithful boyfriend/husband. I probably would have been a worse philanderer had it been easier. I never had groupies. I was okay looking, but women didn’t fall over themselves vying for my attentions. I’ve heard it said that a man is only as faithful as his opportunities. While there is some truth to that, strength of character can overcome these opportunities. For about a decade, I didn’t have that strength.

Kris seemed to overcome many of his demons with a religious conversion and an eye-opening movie role. In the 1976 version of “A Star is Born,” Kristofferson played opposite Barbra Streisand as an alcoholic self-destructive rock and roll star and songwriter. Over the course of the movie, Kristofferson gets more and more destructive and eventually kills himself while driving a car recklessly. Kris must have seen the movie as semi-autobiographical and become aware that if he didn’t change his ways, he too would likely face an early demise. At about the same time, Kris converted to Christianity and wrote the song “Why me?” (Sometimes called “Why Me, Lord?” when sung by other artists.) This song was his only number one record as a solo artist.

For me, I never starred in a movie, nor did I have a religious experience to straighten me out. I took the Erhard Seminars Training (EST) in 1980 — with positive results. The training is loosely based on Zen principles. It has generated substantial criticism, but for me it was the single-most important event on my journey towards being a responsible human being. I have had no contact with the organization for more than 40 years, which has morphed a few times but still exists, but it remains an important part of who I am.

When Kristofferson’s musical career was floundering in the mid-1980s, he teamed up with Willie Nelson, Waylon Jennings, and Johnny Cash and formed “The Highwayman.” These four artists, called outlaws by some, were as big as you get in country music. At the time, being less aware of Kristofferson’s achievements than I am now, I was surprised when he was included in the group, rather than, perhaps, Merle Haggard. While the group sang hits from each of them, about 40% of those songs were written by Kris. That’s why he was in the group. 

For me, my late-in-life partnership was the “Gambling with an Edge” podcast, especially when my co-host was Richard Munchkin. Prior to that show, I’d been a magnet for Internet criticism. People who did not know me regularly posted negative things, often untrue, about me. When the show became a hit because of the people we interviewed, much of that criticism stopped. For that, I am grateful.

Finally, both Kris and I eventually got marriage right. His third wife, Lisa, bore him five children and stuck by him 40 years until his death in 2024. By all accounts, they were happy. For me, I’ve had more than three wives. Bonnie came to me late in life. We recently celebrated our 11^th anniversary — and both of us expect it to last for the duration.

So many of the good-and-bad events of my life parallel those of Kris — and I find that I personally respond to his lyrics. Maybe you can’t relate to “Well I woke up Sunday morning with no way to hold my head that didn’t hurt,” but I can. My favorite Kristofferson song, “Jody and the Kid,” was never a commercial success. But look it up on YouTube. You’ll be glad you did.