Happy 2026! As we start the New Year, I want to share the opening of the book I am writing, “All Over the Map: A Political Journey from Left to Right.” There are more chapters to share and I will keep you updated as the year goes along. Winners & Losers regular programming will return next week.
All Over the Map: A Journey from Left to Right
Introduction
Political scientists routinely describe the current division in American politics as “tribal,” as if the seething intensity each side feels for the other is something new. I was born into a family whose political roots run deep, and I can tell you, unequivocally, that politics has always been tribal.
I grew up in an Oklahoma, still caught between its “Grapes of Wrath” complex and the “wind sweeping down the plain” images from the Broadway musical. I went door to door with my father when he was running for office, and I collected campaign brochures like baseball cards. I do not recall a time in my life that I did not know who the political allies and enemies were.
I learned West Coast politics among the tree-hugging hyper-progressive elites of Oregon and then moved east, where I watched the Democrats from the wealth belt of New Jersey push all their chips into the middle of the table to keep Bill Clinton in the presidential race. I worked for the City of New York as it buckled under the crushing weight of bankruptcy, garbage and disease, and I saw it rescued, against all odds, by a Republican named Rudy Giuliani.
I watched Donald Trump sort through his early wives and figure out his shtick in New York and I saw how sex, race and ethnicity all become political forces before identity politics reduced them to a chorus of whining grievances.
I helped the Democrat machine elect the first African-American mayor of New York City and worked on the U.S. Senate campaign of Geraldine Ferraro, the first woman to run for vice president on a major party ticket. Later, I worked for over a decade for the Lieutenant Governor of Texas, an outspoken right wing leader who serves as a symbol of the conservative movement in Texas and its spokesman in many parts of America.
I called myself a socialist Democrat, progressive and decidedly left-wing before I called myself a conservative, and arrived at the place I mostly inhabit now—the proud, bright red right wing, (though not the fringe) of the Republican Party.
One thing I have never called myself is a moderate.
Politics is a difficult habit to kick, not that I have ever really tried. Unlike Alexander Hamilton, I have often been fortunate enough to be in the room where it happened, or at least in the building where it happened or the city where it happened. That is what keeps you coming back.
In 1988, after the Democratic team was crushed in the presidential election, I asked the legendary Democrat political strategist Robert Shrum for his advice on what I should do while we waited out the four year purgatory before the next election. He told me I had to decide if I wanted to be a pundit or a player.
At that time, nobody knew more about politics than Bob Shrum, so I figured I had to pick a lane. But every time I embraced being a political player, I found myself compelled to create the punditry and policy to explain the moment. However, even after I established myself as an analyst and a pundit, I could never stay off the political playing field for long. I had to get back in the game.
Decades later, it is clear Shrum was wrong. I didn’t have to choose. I have been a political player and a pundit my entire life and have left a written trail, going from political battle to policy wars across the country. The question I get most often is how did I get from way over there on the left to way over here on the right?
“All Over the Map” is the very long answer to that question.
Oklahoma Reds and Liquor-by-the-Drink
All four of my grandparents were living proof that politics has always been tribal. They were all born in the last decade of the 19th Century: 1889, 1891, 1895 and 1896. They migrated west from Tennessee, Illinois and Arkansas, and north from Texas, and settled in the Oklahoma oilfields at the turn of the century. They settled in a place called Oilton, three miles from the banks of the Cimarron River, and just west of the line that separated Indian Territory from Oklahoma Territory.
My father’s grandfather fought for the Union in the Civil War, and my other three grandparents were grandchildren of Confederate soldiers. But the Civil War did not drive the everyday narrative of any of them, even though they were all born about 30 years after Appomattox and must have grown up hearing about the war that their families had lived through.
Instead, they were part of what some call the “recovery generation,” after the Civil War. About 20% of all children were gainfully employed by the age of 10 at the time, and the stories my grandparents told all stemmed from hard times and survival—which had shaped their world view and defined their politics.
Their thought leader was Will Rogers, the legendary Oklahoma-born humourist and political commentator and, like him, they believed Oklahoma was the heart of the country. They thought the red clay of the Cimarron River was the lifeblood of the nation, kind of an Okie Nile. I was baptized in that river.
My grandmother told me that her father had been part of the socialist movement known as the Oklahoma Reds that grew out of the dustbowl. The Working Class Union (WCU) in Oklahoma elected almost 200 people to the state legislature between 1915 and 1917, and their gubernatorial candidate got 30% of the vote in 1916. They were anti-capitalist isolationists, driven left by the exploitation of farmers by Northeastern banks. It’s not clear whether my great grandfather was a Socialist or a Communist, but whichever it was, my grandmother did not share his views.
Late in her life she told me, “My father was always going to Socialist meetings and talking about what was said. He had Socialist magazines and newspapers all over the house. I read them all and I didn’t believe a word of it. So in 1918, when women got the right to vote in Oklahoma, I went right down and registered Republican.”
She voted Republican her entire life, much to the consternation of my father who thought her political choice reflected her ignorance. The Democrat Party was the party of working people. Oklahoma was a Democrat state and had been since the beginning. To vote Republican meant you were opting out of most elections, since the victor of the primary was always the ultimate winner. The only other Republicans anybody knew about were African-Americans.
Her husband, my grandfather, was also a Republican for family reasons. He told me that because his father had fought for the Union, in “Lincoln’s Army,” he voted Republican in his honor.
In my mother’s family, politics was driven by cultural issues. My mother’s father had been a bootlegger during Prohibition, and our family albums include several arrest and conviction clippings. He mostly shifted away from criminal activity after Prohibition ended, but stayed in the beer joint and night club business, sponsoring the occasional floating poker game on the down-low.
My grandfather’s bar had a big picture of Will Rogers on the wall, the same Will Rogers who said he “didn’t belong to an organized political party; he was a Democrat.” I can never remember not knowing that joke.
Rogers is most famous for saying is that he never met a man he didn’t like, but his political commentary was all based on “us”—the Everymen of Oklahoma and America and “them” —the rich, the elites in the Northeast and the ridiculous people in Hollywood. He made fun of both sides, but it was tribal.
In my first trip to Washington, D.C. after college, my family made sure I found the statue of Will Rogers in the Capitol—Oklahoma’s contribution to Statuary Hall. It’s in a prime spot outside the U.S. House Chamber, and television crews today call it the “Will Rogers stakeout” because they can ambush lawmakers there and force interviews.
The big picture of Will Rogers in my grandfather’s pool hall may have provided him with the inspiration to keep battling to legalize liquor-by-the-drink in Oklahoma. It was legal to buy a glass of beer (nobody drank wine), but a bar could not dispense hard liquor.
Most bars, including my grandfather’s, got around the law by declaring they were private clubs and handing out membership cards to customers to display if the police showed up. The liquor bottles all had people’s names written on them—to prove that the members had brought them in and the bar was just serving them. This charade went on in honky tonks and fancy hotels. It was the Oklahoma way.
Liquor-by-the-drink was on the ballot every election year when I was growing up. My grandmother always had a Legalize Liquor by the Drink bumper sticker on whatever big Oldsmobile she was driving.
I asked my father once about life during the Depression, and he told me that 1933 was the worst year. There was no money, and he and his father had worked for food because everyone was trading by a barter system. But he added, “Of course, your grandfather had money.” Apparently, the bar business was always good.
My bar-owning grandparents were “yellow dog,” straight-ticket Democrat voters, but it didn’t help them. They died in the early 1980s before liquor-by-the-drink became legal in Oklahoma.
All Politics Really are Local
All four of my grandparents made it very clear to me that politics mattered and understanding it was important, but it was my father who showed me what living a political life meant. He ran for city council when I was in elementary school, and later was elected mayor when I was in high school. He was always in contested elections, often engaged in the very bitter battles that define small town politics. I grew up campaigning.
Although my father had strong political views, he was a reluctant politician. Going hungry during the Depression haunted him throughout his life. So did his time fighting in four theaters of war during World War II. He remained angry that President Franklin Roosevelt had promised that “no American son would have to fight in more than two theaters of war,” but he’d been shipped into four.
He didn’t think he’d make it back, but he did and returned to the oilfield job he got when he graduated from high school. While he was still, in his 20s, he was urged to run for city council. He seemed to exemplify the greatest generation before they knew they how great they were.
After a few terms on city council, he was elected mayor—a job which famously paid one dollar a year—and pushed forward an expansive agenda for our town starting with buying the water company, a move that meant that anytime someone had low water pressure, they called our house to complain.
The track survey for our little town was wonky, so he walked every block and assigned each house its proper number. Then he got the Boy Scouts to sell everybody new house numbers.
My parents supported President Lyndon Baines Johnson, and after he launched the War on Poverty my father got a call from a guy in the newly established office of Housing and Urban Development (HUD) who wanted to meet with him and get a tour of our little town. My dad was very excited about this because he had some ideas about building some housing for old people and young families who really needed it.
His real job was in the oil fields, so on the day of the meeting, he had to take off work and change his clothes before he could meet the HUD man. He made it back to our house just in time for dinner.
When my Mom asked him how it went, he laughed and said that the man from HUD had condemned the entire town, pronouncing every house (including ours) as substandard. He wanted to tear them all down and build new ones.
My mother was wild eyed with disbelief. Our house had been given to us by my grandfather, and my Dad had fixed it up. We lived next door to the house where my mother was born. She told my father unequivocally they he could not let them tear down our house.
My Dad assured her that wouldn’t happen, dismissing the HUD men and his colleagues as “crazy bureaucrats.” It was the first time I ever heard that term, but it ultimately helped me understand the entire War on Poverty.
The HUD man never returned and no houses were torn down. A couple years later, I was home from college for the weekend and my father asked me to help him fill out a HUD grant application to build the low-income rental housing he’d envisioned. The town was awarded the grant and built 20 units across from the baseball field. They are still there.
I don’t think our neighbors ever had any idea what he’d saved them from.
Sherry Sylvester is a Distinguished Senior Fellow at the Texas Public Policy Foundation and the former Senior Advisor to Texas Lt. Governor Dan Patrick.
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