Forget about death and taxes. Today, there are only two sure things in life: Every few years Rick Perry will run for office, and every few years Rick Perry will grind his opponents into dust. Since 1984, the man once derided as “Governor Good Hair” has participated in ten contested elections*  and won all of them. A few were against relatively weak opposition, but many were against prominent figures who were expected to give Perry a run for his money. Jim Hightower, John Sharp, Tony Sanchez, Chris Bell, Carole Keeton Strayhorn, Kay Bailey Hutchison, Bill White—you could competently govern a medium-sized republic with political talent like that. But all of them fell to Perry’s deep coffers, disciplined campaign style, occasional refusal to debate, and (semi-) popularity among Texans. What is it like to run against the man who may well be the most successful state politician in Texas history? To find out, we spoke to eleven people with intimate knowledge of what is, after dying and paying taxes, the most unpleasant experience a politician can endure. Mitt Romney, Michele Bachmann, Barack Obama: Read closely.


1984 Democratic primary for state representative (District 64)


Kenneth Neighbours (D), lost with 22 percent*

Perry won his first race handily, and in District 64 in the mid-eighties, winning the Democratic primary was equivalent to winning the general election. Neighbours, a rancher and longtime history professor at Midwestern State University, in Wichita Falls, died in 2002. During his life, he kept regular journals, which are now held at the University of Texas at Arlington. Several of the entries from 1984 address his campaign against Perry.

May 1: Forum at Granbury. Wrote speeches for tonight. Went for haircut. Minor local candidates spoke first. Then leg. cand. Rick Perry had county remote official stand in for him. Said he was socked in by weather in Mi Wells. I read my paper last.

May 5: Primary election 7 a.m.–7 p.m. Went to Winn Dixie. Young man sacking groceries invited me inside where it’s cool . . . middle-aged woman asked whether I knew Rick Perry. I said, “Yes, he’s cute.” She turned red and accused me of breeding, training, and selling race horses for amateur betting. First malicious and false rumor I’ve heard. Shriner man laughed heartily at my calling Rick cute . . . Left Winn Dixie at 6:45. Ate at cafe next to Holiday Hills . . . drove my pickup home. Bill used portable radio and phone to get results. Rick Perry won.


1986 Democratic primary for state representative (District 64)


W. R. “Bob” Hailey (D), lost with 24 percent*

Perry’s second race was not much more challenging than his first. Hailey, a Fort Worth public school teacher and principal, as well as a World War II veteran (he is said to have shot at Erwin Rommel’s car), died this past June. His daughter Celeste Sainte-Marie recalls that he refused to take money for the race so as not to become indebted to anyone. “He was always more concerned about the little man who can’t take up for himself,” she says. “The average taxpayer.”


1990 general election for agriculture commissioner


Jim Hightower (D, incumbent), lost with 48 percent

By 1990, Perry had switched parties to run against Hightower, the incumbent ag commissioner. Best known today as a radio host and author, Hightower at the time had a national profile as Texas’s most liberal and populist statewide official. That wasn’t enough to help him hold on to his job, though he came as close to defeating Perry as anyone else has, falling short by a little more than one percent.

Hightower: The Republicans were pissed at me, because I had gone after Bill Clements when he was running against [Governor] Mark White. And the chemical lobby despised me, and the Farm Bureau hated me too. They were pushing two pieces of legislation, one to remove my authority for pesticide regulation and the other to make the office appointed [by the governor]. That was unsuccessful, but it led to this committee hearing, and Perry was the chair of that committee. I suppose Karl Rove looked at him and thought, “Here’s a guy who’d look good in chaps and who is an empty slate and we can make him an offer that he’ll grab because he’s a political opportunist.”

I guess I’d call Perry’s campaign ghostly, because he was not the main character. Rove, who recruited him to switch parties and run against me, directed the effort. Perry was not any good at campaigning; he had no idea how to deal with Houston and Dallas and San Antonio and South Texas and all that, though I don’t know of any inappropriate comments that he made, because he wasn’t really getting any media. Rove got frustrated with him and sent him out to West Texas to attend Farm Bureau county meetings while Rove raised, I think it was about $3 million, and threw it into TV ads against me. They ran ads of me endorsing Jesse Jackson—ran that in East Texas. One ad showed a hippie setting a flag on fire and throwing it on the ground, and my picture came up out of the flames. So I had supporters in Dallas and Houston and East Texas who said, “Well, I liked ol’ Hightower but I didn’t know he burned flags.”

There was a debate on Channel 13 in Dallas. Just the usual stuff. He tried to use some of the Rove negative things, including the flag-burning stuff, I think. Off the cuff, he was nondescript. He hadn’t really developed any political chops at the time. Obviously he has since. I think he’s a good campaigner. I think that’s the one thing he actually does well, as opposed to actually governing or having actual ideas or principles.


1994 general election for agriculture commissioner


Marvin Gregory (D), lost with 36 percent

Gregory, a 72-year-old chicken farmer from Sulphur Springs, served on the Texas Agricultural Finance Authority with Perry in the early nineties and then, after switching from the Republican party to the Democratic party, ran against him for agriculture commissioner in 1994. Today Gregory says he will support Perry for president.

Gregory: He hasn’t changed that much since I first met him. He doesn’t make a lot of loose talk. He doesn’t say things that you would use against him later on. He’s not his own enemy, is what I would say. If you look at our president today, he’ll say one thing one week, next week he says something else. So there’s always room to go back and say, “Well, you said this then. What’s the difference now?” And you never hear that much from the governor.

There was never a doubt in his mind, I don’t think, that he was going to win. So he went on about his business; he ran it like he was going to win it. We had debates at different places, and he just basically didn’t show up most of the time. And you can’t blame him, because when you’re ahead, [participating in debates is] not a real good idea.

Whoever runs against him, they better have all their irons in the fire when they come after him, because he’s going to have his ready to go. He don’t have many skeletons in the closet. Just be ready for a fight, ’cause you’re going to get one.


1998 general election for lieutenant governor


John Sharp (D), lost with 48 percent

A veteran of the state House and Senate, Sharp, who had been a friend of Perry’s at Texas A&M, gave up his position as comptroller to run. But he wasn’t quite able to close the gap. He recently announced that he would run for the Senate seat that Kay Bailey Hutchison is vacating.

Sharp: Running against Perry is like running against God. Everything breaks his way! Either he’s the luckiest guy in the world or the Lord is taking care of him. In 1998 Governor Bush told Bob Bullock he was going to stay out of our lieutenant governor’s race, according to Bullock. Then Bush realized that he could not run for president if it meant leaving office would elevate a Democrat to governor. So he was forced to get involved, and his parents ran ads for Perry.

He’s a relentless campaigner. I was up at five every morning just to match his schedule. Our money was about even, until an extra million dollars miraculously came to him at the last minute. Two weeks before the election, the largest flood of the century hit the Eighteenth District, which I’d represented in the state Senate. The flood inundated towns all along the Guadalupe River, with massive flooding in Gonzales, Cuero, and Victoria, my hometown. No one thinks about voting when their house is flooded. I received 70 percent of the vote there, but, of course, it was a record-low turnout. It’s hard to get out the vote from a boat. I don’t know if God is calling Rick Perry to run for president, but if he runs, the other candidates are going to need a big dose of magic and a lot of shoe leather. He is focused with a capital F, and his political advisers are the best I’ve ever seen. If you run against Rick Perry, you better pack a big lunch.


2002 gubernatorial general election


Tony Sanchez (D), lost with 40 percent

When George W. Bush won the White House, Perry acceded to the Governor’s Mansion, which gave him the advantage of incumbency in his first gubernatorial run. Still, Democrats had high hopes of knocking him off with Sanchez, a wealthy Laredo oilman and banker. The campaign was run by Glenn Smith, a former Houston Post and Houston Chronicle reporter who had worked for Bill Hobby and Lloyd Bentsen and headed up Ann Richards’ successful race for governor, in 1990. The Perry-Sanchez contest was hard-fought, but the most memorable moment was surely a controversial ad from Perry that asserted that Sanchez should have known that his savings and loan company was laundering drug money. Sanchez declined to be interviewed about the race. Smith currently runs the political website

Smith: I’d known Rick Perry since I’d covered him as a reporter back in the eighties and he was in the House. I knew he had a disciplined team around him, that he shouldn’t be underestimated, that they were coaching him very well and that he would follow instructions very well. And he also had the benefit of watching George W. Bush do just that: run very disciplined campaigns, repeat the same message over and over, and minimize mistakes.

In the summer of 2001, Bush wasn’t doing well, the Enron scandal had happened, and Perry looked very vulnerable. But after 9/11 things turned around nationally for the Republicans. We had a lot of issues going for us—public education and higher education, high insurance rates, cleaning out the corruption. All of those worked pretty well, but as soon as Bush rattled the saber with regard to the Middle East, it erased all those issues from voters’ minds. National issues just so dominated the minds of voters that they didn’t have the time or inclination to worry about almost anything else, including those things we wanted to talk about.

I think [the S&L ad] was racist. I think he used code to imply that a Hispanic candidate had a part in the murder of a couple of DEA agents. I think they knew that was the effect of it, and it was unconscionable and immoral. I’ve never seen an ad like that anywhere, any other time, by anybody. I don’t really expect fairness in political campaigns. If you want fair, go to the circus, you know what I mean? But I think that ad was way beyond normal ethical bounds, and after it went up, Perry started to lengthen his lead over Tony, which at times was pretty small, even late in the campaign.

I would tell whoever goes up against him, Don’t underestimate his ability to perform on the stump. He doesn’t make mistakes. He follows instructions. He’s not going to have a “macaca” moment.


2006 Republican gubernatorial primary


Larry Kilgore (R), lost with 8 percent

An Amarillo native and Air Force veteran, Kilgore has been an outspoken proponent of the Texas secessionist movement. In 2006 he challenged Perry in the Republican gubernatorial primary and came away with less than 10 percent of the vote. Two years later, he challenged John Cornyn for the Senate and earned a notable 19 percent.

Kilgore: I didn’t think I had a very good chance against Perry, but if there happened to be a huge downturn on Wall Street, if there had been a nuclear weapon that exploded somewhere, say, in Washington, D.C.—I’m just talking some scenarios; hopefully they don’t happen—if some of those items would have happened, then it would have changed dramatically. People would have said, “Hey, Texas can be free and independent. Let’s go with Larry instead of trying to stay with the United States and they take all of our money.”

The way we do campaigns here in the United States, folks give money and the people with the most money usually win. If I was more of a pro-business-type person, then it would be much easier for me to raise cash.


2006 gubernatorial general election


Chris Bell (D), lost with 30 percent; Carole Keeton Strayhorn (I), lost with 18 percent; Kinky Friedman (I), lost with 13 percent

Bell, an Abilene native and former Houston councilman and U.S. congressman, won the Democratic gubernatorial primary, only to face three larger-than-life figures in the general election: not only Perry, but Friedman and Strayhorn as well. After an impressive debate performance, Bell trounced the two independents but lost to Perry by nine points. Following an unsuccessful 2008 run for the state Senate, he returned to his private law practice.

Bell: The thing that amazed me about Perry was his luck. He’s the luckiest politician in the world. At the time I ran against him, there was a lot of criticism of him in Republican circles, and I really wasn’t that concerned about him. He had a reputation for hiding as much as he could and not appearing at joint forums. That being said, I knew he’d be formidable. He’d have a lot of money and would be well advised, as he always had been. The advantage we had was that he was unpopular and had made a lot of people mad.

We had one debate, which was the first and only time we met until after the election. It was an obvious part of Perry’s strategy to make sure there was little interaction, whereas I saw Strayhorn and Friedman quite a bit. None of that with Rick Perry. He kept to his planned schedule of going to friendly Republican audiences.

At the debate, Kinky and Carole were horrible. Perry got through it and didn’t make any major blunders. But after the debate everything changed for me. [Plaintiff’s lawyer] John O’Quinn put in a million bucks. Once I had money and could go on TV the whole complexion of the campaign changed. I started going up in the polls and moved from the last paragraph in each story to the first paragraph.

I was making headway, and Perry goes up with his first attack ad of the campaign, talking about “the sharks in the water,” the sharks being the trial lawyers. They started attacking me for taking that money from O’Quinn. Then the Chronicle poll came out; we knew we were surging but the poll did not reflect that. It showed Perry with a solid lead and Carole and me neck and neck. To win, there had to be a great distance between [me and Carole], and the distance wasn’t there. I figured that poll was gonna kill the enthusiasm, and sure enough, the next day there was a reception and hardly anybody showed up.

The guy catches more breaks than anyone in the history of man. Sixty-one percent of the people voted against Rick Perry, but he had two egomaniacs running against him.

The former mayor of Austin and onetime Texas railroad commissioner, Strayhorn was serving as state comptroller when she got in a feud with Perry, a fellow Republican. Rather than face him in the primary, she entered the general election as an independent and unsuccessfully tried to get herself listed as “Carole Keeton ‘Grandma’ Strayhorn” on the ballot. She placed third.

Strayhorn: I got into the race because of issues I cared about—education, our forgotten foster children, expanding CHIP, opposing the Trans-Texas Corridor. With four people in the race, I really wasn’t running against Rick Perry. There was a window there, but our real opponent was the system. We had to spend a huge amount of our time on petitions to place our name on the ballot. In two months we gathered a quarter of a million signatures of registered voters who had not voted in either primary. It cut down on our campaigning, and it cost a lot of money. The biggest factor was that, in the end, people went back to straight-ticket voting. You’re really fighting the system to run as an independent in Texas. Texas needs a true open primary.

Friedman, the songwriter, mystery novelist, and humorist (and sometime TEXAS MONTHLY contributor) gained national attention for his campaign, the slogan of which was “How Hard Could It Be?” Yet despite attention from media outlets like the New Yorker and 60 Minutes, he finished a distant fourth.

Friedman: Rick didn’t really campaign a hell of a lot. He didn’t have to and he knew it. He had that election wrapped up. Money elects you in politics. By the time we spent the six million bucks we raised to get on the ballot we were pretty much broke.

He’s got really good people working with him. His campaign manager—that’s a guy that anybody would like to have. I think they do what they have to do to win. They don’t get into bitchy little battles with people when they don’t have to. I didn’t see a lot of snide comments coming from them about anybody.

Perry was a gentleman during the debate. But it was an off night for me; I was kind of off my feet. One reason is, I like Rick. I didn’t want to have to attack him the way you would have to attack someone when you know that he’s winning. I think Rick and I, although we disagree on a great many things, are incapable of resisting each other’s charm.


2010 Republican gubernatorial primary


Kay Bailey Hutchison, lost with 30 percent; Debra Medina, lost with 19 percent

A onetime state representative and treasurer who had won four elections to the U.S. Senate, Hutchison likely hoped that Perry, after ten years in office, would step aside and let her take the Republican nomination for governor. Instead, Perry ran again and beat the popular lawmaker handily. Hutchison declined to be interviewed about the race, as did multiple members of her campaign staff, many of whom are currently working for other candidates. Matt Mackowiak, her Senate press secretary at the time the campaign began, was a frequent commentator on the 2010 race, though he did not have an official role within the campaign.

Mackowiak: The individual issue attacks that Hutchison had—things like HPV, Trans-Texas Corridor, and the eminent domain issues—weren ’t breaking through or piercing the overall dynamic that Perry was able to create very early on. He did this partially by adopting the tea party identity before anyone really knew its full power. In April 2009 no one really knew what the tea party was. So it was something I think that Senator Hutchison wanted to be somewhat cautious about. She didn’t know what it was; she didn’t know what they were trying to do at the time. Of course she thought that the federal government was too big. Of course she thought that spending was too high. I think at some level she fully connected with the reasons the tea party came into existence, but she didn’t quite understand how to tap into it at that time. And Perry’s instinct was to tap into it immediately. I think that inoculated him from a tea party challenge. Medina could have been a much greater threat had he not adopted the tea party platform early on in a direct way.

One of the biggest surprises of the 2010 Republican gubernatorial primary was the strong showing by Medina, a nurse and small-business owner from Wharton. Despite being a largely unknown and inexperienced politician from the party’s libertarian-oriented Ron Paul wing, Medina impressed many with her debate performances.

Medina: I think a lot of people marveled at Perry’s campaign. It was pretty widely reported at the time that he didn’t do a lot of the traditional stuff; he went to more of a social media marketing model. I don’t know if that works for anybody that hasn’t been in office for twenty years, but it worked for him. He just took that “I’m the governor, I’m going to be reelected, and I don’t have to mess with you people from Texas” attitude. They took the position for a very long time that I didn’t exist, and I think it absolutely worked for them.

But I won both of the debates hands down. Perry’s demeanor when he initially came onto the stage the night of the first debate—it wasn’t serious. It was jovial, like “Great to be here!” It was almost comedic, you know? It was kind of a Three Stooge-y feeling. And that’s what was reported—that his answers were not good, he didn’t take the debate seriously, he may be a little arrogant. He was very confident in his place as the governor, and he got shown up. In fact, they both did. And I think that’s really the thing—that we had two people who spent almost their entire adult lives in service to our state who knew less about what was going on in our state than a nurse from Wharton, Texas.

His demeanor in the second debate was much more serious. But I still think I beat him.

After the primary election, I think, we initiated a call to Perry, and he agreed to take it, and we set up a time to talk. And I remember getting off the call and thinking, “I know why he wins campaigns; he’s a really smart guy.” People from all parts of the state were telling me to endorse him, and I was like, “Until he does something that’s consistent with the ideas that we have, how can I endorse him?” So I thought, he’s going to say to me, “You know, Debra, you really need to.” And he didn’t. He never did mention it. He didn’t put me in a position to tell him no.


2010 gubernatorial general election


Bill White (D), lost with 42 percent

Democrats who hoped that the popular former Houston mayor would break Perry’s nine-race winning streak were in for a disappointment. Despite frequent claims that White would make it a close race, Perry outmaneuvered him at every turn, refusing to debate unless White released all of his tax returns (which he did not do) and accusing White of profiteering off of Hurricane Rita. White lost by a thirteen-point margin.

White: Rick Perry has a justifiable reputation as somebody who lives and breathes politics and has a fierce determination to stay in office. [I met him] decades ago at a Texas Lyceum event when he was a young Democrat. He was a handsome young man who worked the crowd, but there were a lot of ambitious young people in the statehouse, and I don’t recall him sticking out particularly.

He raised more money than I did, but from a much smaller number of donors, and some of his donors gave millions. His principal handler is a Mr. [Dave] Carney, who lives in New Hampshire and is charging the campaign millions of dollars in fees, but he’s a real pro, and Perry tends to keep on the script that’s given him.

I sought to debate, but he did not want to debate and defend his record. He very rarely campaigned in person. When he did, he chose public appearances, where questions from the press would be limited. If his handlers had exposed him to more questioning, then he might have responded in a way that hurt him. One of the few—perhaps the last—impromptu sessions he had with a journalist occurred about six months before the election: After a meeting with BP executives he said that the oil spill might have been caused by an act of God. After that there weren’t many impromptu sessions with journalists.

His strategy was to claim that Texas government was in good shape, when, obviously everyone now knows, it was not. Perry ran massive amounts of advertising in Houston in the last six weeks. About two thirds claimed that Texas state government was in good financial shape and took credit for the fact that Texas had grown faster than other states, despite the fact that it has for one hundred years. The other ads had pictures of me and President Obama. Some, especially outside the Houston area, attacked Houston and my performance as mayor. Polls showed that he pulled into a lead after the massive advertising barrage principally because of the influence on independent voters who didn’t like the growth of government in Washington.

There were also some silly things that happened that are still hard to believe. One consulting firm of his created artificial people to tweet. [The campaign] wanted to question my support in the African American community, but they couldn’t recruit an African American person to do it, so on Twitter they used a stock photo of a black person. One of the people who supported my campaign clicked on the image and found out it was a singer from Atlanta. The Twitter address was registered at the same location as one of Mr. Perry’s political consultants.

Perry and I spoke briefly the night he won. I told him congratulations and that I hoped he would do well as governor. We both acknowledged that our wives are better people than we are.