Al Simpson May Still Be the Most Interesting Man in Wyoming

“What I used to call THE BIG TENT is now what I call THE BIG TENTACLE,” former Sen. Al Simpson told me on a sunny Wyoming afternoon recently.

The retired U. S. Senator, 90, has long been critical of how Wyoming Republican politics has become more exclusive compared to the “Big Tent” plan used by himself and promoted nationally by former president Ronald Reagan. It implies that anyone who believed in basic Republican principles is welcome in his version of the party. 

He was speaking in reference to July 7, when President Joe Biden gave him the Presidential Medal of Freedom, the highest civilian honor available to an American.

Simpson, who lives in Cody, journeyed to my hometown of Lander recently to attend the funeral of a wonderful woman named Eileen Oakley. Eileen died of colon cancer at the age of 75. Al’s son Colin is married to one of Eileen’s three daughters, Debbie. Debbie is an outspoken Wyoming political personality, herself, but that is another story.

Big Al (who stands 6-7) continued: “When I go to Washington, I am going to say that simply I am an American who lives in Wyoming. I will not be saying that I am a member of the Wyoming Republican Party.”

His dismay, over the hard conservative direction the Wyoming Republican Party has taken this century, has been evident for years. Being pro-choice, Simpson has found himself isolated from the majority of members of the state’s current GOP for decades.

He likes to single out current state Republican Chairman Frank Eathorne for criticism. “I would like to discuss family values with him sometime,” he said. 

He also has nothing good to say about former President Donald Trump, which does not endear him to Republicans in a state that voted more overwhelmingly for Trump than any other in both the 2016 and 2020 presidential elections. 

Simpson retired in 1996 and has long claimed it might be impossible for him to win the election these days. He won three elections to the U. S. Senate, mostly by wide margins. He was an amazingly influential member of the Senate, serving as both Majority and Minority Whip for ten years.

Another Wyomingite to receive the Medal of Freedom is his friend Dick Cheney, the former Vice President. Cheney was given it in 1991.

At the ceremony, President Joe Biden called Simpson “the real deal” and complimented his ability to work in a bipartisan manner in Congress and do what was best, despite outside pressures and political polarization stating that his “conscience was his guide.” 

“He never allowed his party or state or anything get in the way of the way he felt was right,” Biden said. “He believed in forging real relationships even with people on the other side of the aisle and proving we can do anything when we work together as the United States of America. 

“It matters, it matters, it matters,” Biden continued. “We need more of your spirit back in the United States Senate on both sides of the aisle.”

“Simpson and Biden served together for 18 years in the Senate, spending seven years together on the Senate Judiciary Committee. Biden said Simpson was one of the “finest men he’s ever worked with.”

“He never takes himself too seriously, nor takes me seriously,” Biden 

Some years ago, I ran a statewide contest to identify Wyoming’s most interesting person. I used the popular beer ad campaign, as an example, which was used as a spokesman for the most interesting person in the world. Thus, I sought the most interesting person in Wyoming.

Simpson won because of his amazing record of service to Wyoming, to his country, and also for his wit and amazing life outside of politics. The man is unique. A true Wyoming original.

Here is what I wrote when Al was overwhelmingly picked for that singular honor:

Picture this: the most interesting man in Wyoming is surrounded by his beautiful wife, his daughter, his pretty daughters-in-law, and his pretty granddaughters. He raises a glass in a toast and looks into the camera and says:

“I don’t normally drink, but when I do, I drink Wyoming Whiskey.”  

Coincidentally, he had recently been featured at the time in a promotion for the Wyoming Whiskey distillery where he had his own barrel of bourbon made. Big Al carefully and methodically signed and numbered all 216 bottles in his name. Congratulations to this amazing man and his family.