Not long ago I got an important private email message from Milward Simpson, director of the Wyoming Parks and Cultural Resources department, and opened it thinking he was reaching out to sharp political thinkers like me as he considered a run for the seat vacated by Rep. Cynthia Lummis (R-Wyo.) in the U.S. Congress. Simpson later cleverly covered his tracks by notifying me (and a few thousand other confidantes) that a hacker had gotten into his office email and was trying to infect us all.

Now, after a couple of weeks stripping all the data out of my computer and thinking up new passwords (the misspelled middle name of the bassist in Deep Crimson, followed by the number of billions bankrupt Arch Coal is in the red), it’s time to think again about the prospect of Simpson running, even if he hasn’t thought about it. Because it’s just too much fun imagining Democrat Milward against Liz Cheney, who is rumored to be about to throw her cowboy hat into the ring on the Republican side.

Better than Jeb Bush versus Hillary Clinton — and about as likely.

(Jeb was recently seen personally and energetically deporting all children of immigrants from Florida, with a brief layover and photo op in New Hampshire, including his daughter by his Mexico-born wife Columba. He reminded reporters that he would rather the daughter’s drug-addiction remained a private family matter, unless, perhaps, they would like some video of him crying about it.)

(Hillary last month sent out Chelsea on the campaign trail to rip Bernie Sanders a new one on the issue of universal health care — the surgery for which will be covered by the congressional health plan, which he has and you don’t. It’s not clear if Chelsea charged her usual $65,000 speaking fee, but the poor girl is pregnant … in any case, she will continue up until her third trimester to aggressively attack Hillary’s most formidable opponent…. Bill Clinton has not yet responded.)

But where were we? Oh yes: Simpson vs. Cheney, the dynasty battle for Wyoming’s sole, or soul, seat in Congress. What a race it could be! The daughter of Wyoming’s most famous figure, former Vice-President and hunter-of-anything-that-moves Dick Cheney, against the nephew of Sen. Al Simpson, best friend of Presidents and octogenarian radio sex advisor. The two seniors have been buddies for ages, since the days when they campaigned together like a couple of frat brothers, threatening to throw pies at hecklers and masquerading as each other to unsuspecting radio interviewers.

But that friendship was strained two years ago, when Liz Cheney decided to get in the race early for the seat of retiring U.S. Sen. Mike Enzi. The problem was, Enzi’s retirement was still at least seven years away. Al Simpson, who is remembered by every U.S. Senator since 1980 as “my best friend,” remained loyal to Enzi (who is lauded by many as the best Wyoming senator since … well, since Mike Enzi was elected in 1997). This caused a rather public spat between the Cheney and Simpson families, climaxing with Lynne Cheney’s immortal words: “Shut up!” Liz eventually withdrew, citing a previous commitment to fight ISIS in Syria, or maybe it was the War on Coal.

Of course, political dynasties are tricky. It’s not clear, frankly, whether either Al Simpson or Dick Cheney could lately get elected State Auditor in Wyoming. (What’s that, you ask? It’s an office in the State Capitol; the Capitol which will be, for the next few years, located in an old Safeway building. Perhaps the State Auditor’s job is to tally your vegetable purchases at check-out.)

We will not tally, along with the vegetables, the past races in which Simpsons not named Al or Cheneys not named Dick have run and either lost or withdrawn. Nor will we tally the immense field of Democrats who have qualified to enter the race for Lummis’ seat by spending no less than 24 hours (but apparently no more than 48) in Wyoming during the 2014 election. Nor can we add up the dizzying number of Wyomingites who have entered the lists on the Republican side.

There are in fact some formidable gladiators in the Republican primary besides the pizza guy. Tim Stubson or Leland Christiansen, for instance. Never heard of them? Well, they’re not the State Auditor. They’re state legislators with years of solid service. Unfortunately for them, voters across the state are more likely to know the second-year point guard of the Wyoming Cowboys basketball team than they are our Cheyenne solons. For starters, did you know Wyoming had a Legislature?

Republican operatives in Washington, D.C., think that if Liz Cheney runs, she’s a shoo-in. But they also believe, as we see in the Republican presidential race, that voters care foremost about Syrian terrorists Fedexing themselves to our doorsteps, rather than, say, earning a living or curing cancer. If the beltway brilliants are right, then Cheney’s State Department experience, not to mention her knowledge of the street system of suburban Washington, D.C., might be a plus.

What would be an even bigger plus, for Cheney, would be an endorsement from Mike Enzi. Hopefully, such an endorsement would be stronger than Enzi’s farewell to Lummis, a press release praising her for “(sharing) ideas in such a way that people often think it was their idea.” Not likely.

Milward Simpson, of course, faces an even tougher path to Congress than Cheney — the biggest impediment perhaps being that he isn’t actually running. In fact, were we to run into each other on the broccoli aisle at the Wyoming Legislature in Cheyenne, he would probably greet me with a Cheney campaign slogan: “Shut up!”

— Columns are the signed perspective of the author, and do not necessarily reflect the views of WyoFile’s staff, board of directors or its supporters. WyoFile welcomes guest columns and op-ed pieces from all points of view. If you’d like to write a guest column for WyoFile, please contact WyoFile editor-in-chief Dustin Bleizeffer at

Geoffrey O’Gara is a writer and documentary producer based in Lander, Wyoming. He works for The Content Lab, LLC and serves on WyoFile's board of directors. His column, Weed Draw, is named for a remote...

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  1. If the young Milward has the great intellect and humor of Al, then I wish he would run. We are in short supply in Washington DC

    Como Boyle

  2. Dear Wyoming Residents,

    Liz Cheney did past the radioactivity test for present and future.


    Nestor Luis Rivera

  3. Oh please, oh please Milward. Take this wonderful column as a sign from the Cowboy universe that now is your time to be bold!

  4. Thanks. That sums up the Wyoming political landscape nicely.

    Note to self: Must make greater effort to chill out and find the humor.