DRIPPING SPRINGS — When Chip Roy entered the already-crowded GOP attorney general race last year, the Austin congressman thought he could exercise the frontrunner’s privilege to stay out of any negative campaigning.

“I was just trying to run [ads like], ‘I’m Chip Roy, here’s my background, here’s my experience, here’s why I should be attorney general,’” he told a crowd of supporters at a barbecue restaurant Sunday.

Then, he finished second in the March primary behind state Sen. Mayes Middleton, who spent more than $11 million of his own money on ads hammering Roy and touting his own record. The Galveston state senator didn’t clear 50% of the vote, forcing the two men into a runoff and giving Roy a chance to reconsider his strategy.

So at Pig Pen BBQ, on the eve of early voting, Roy got down in the mud and started slinging.

“I’m going to have to say something that’s going to be a little harsh, and I would have felt bad about it a few months ago,” Roy said. “I wouldn’t hire [Middleton] for an entry-level position at the Office of the Attorney General, if he were to apply when I win. That matters.”

Roy and Middleton share impeccable conservative credentials, with virtually no ideological gap between each other. They both focus on election integrity, immigration, cracking down on left-leaning district attorneys and combating the threat of Sharia law, and vow to take the baton from Paxton and use the agency to spearhead the conservative legal movement.

Where they’ve attacked each other, then, is on much more personal ground, focusing on experience, money and loyalty to President Donald Trump. Roy says Middleton is using his millions to buy the race despite a thin legal resume; Middleton says Roy has betrayed Trump and isn’t a true MAGA believer.

The race is already the most expensive attorney general primary in the country’s history, and runoff spending is expected to blow through any previous records. It’s being closely watched by national conservative groups, red-state attorneys general and the White House, and brought a lot of money off the sidelines in the homestretch.

“You look at the Texas attorney general’s office, this is the largest legal power in the conservative movement, nationally, period, end of story,” Adam Piper, executive director of the Republican Attorneys General Association, said. “This is not just about the boundaries of Texas. This is about the entire conservative legal movement and how we promote, protect and preserve freedom for future generations.”

The experience metric

After almost four terms in Congress, Roy entered the race more widely known than any of his opponents, who included two state senators and a former Department of Justice lawyer.

But he’s running less on his record in Congress and more on his time in the courtroom. A former federal prosecutor, Roy also served as Paxton’s first assistant attorney general, helping to set up the agency after he was first elected to the office in 2014. Roy led the agency’s litigation against the Obama administration, targeting the president’s signature environmental and immigration policies in court.

Middleton, on the other hand, has worked exclusively within his family’s oil and gas company. He has a law degree from the University of Texas, and has said he handles civil litigation as part of the company. But unlike Roy, who is approved to practice in the U.S. Supreme Court and the 5th U.S. Circuit Court of Appeals, Middleton is not admitted to any state or federal courts.

“This is the most important position for a lawyer who’s conservative to stand up and defend not just the people of Texas and the state of Texas, but to lead the entire conservative movement for the world,” Roy said from the stump in Dripping Springs. “You need someone who can be in there on Day One, who doesn’t need on-the-job training.”

Middleton, who did not respond to a request for comment, has equated his legal background with Paxton’s when he took over the attorney general’s office in 2015. Paxton was in private practice, including running his own law firm, and worked as general counsel for J.C. Penney.

“But that’s not why we supported him. We supported him for attorney general because of that proven conservative record,” Middleton told Austin television station KXAN. He’s also pointed to his experience running a business, saying he’s the only candidate with “executive-level experience of signing the front of a paycheck and knowing where the buck stops.”

The Texas Constitution doesn’t require the attorney general to even be a lawyer, although they all have been. Paul Nollette, a political scientist who studies state attorneys general at Marquette University, said it’s less about having a specific set of qualifications and more about what the voters will support.

“The strict lawyer skills are probably less important for AGs themselves, especially as offices have increased their staff and really built up their solicitor general’s offices,” Nolette said, referring to the top appellate lawyer within the agency. “But it does matter, do you know how an AG’s office works?”

During the primary, former DOJ lawyer and top Paxton aide Aaron Reitz hammered Middleton for his lack of legal experience, calling him a “child” who is “pretending to be a lawyer for the first time ever.” After finishing last, Reitz pivoted, endorsing Middleton for the runoff over Roy.

“Some criticize Mayes by saying he lacks the legal experience to lead. But that argument doesn’t hold up,” Reitz wrote in an op-ed announcing his endorsement. “For nearly twenty years, Mayes has practiced law as a civil attorney, focusing on oil and gas transactions and litigation, while at the same time serving in state government.”

Middleton has secured a wide array of endorsements from state lawmakers, including Lt. Gov. Dan Patrick, and grassroots conservative groups, many of whom have benefited from Middleton’s largesse as a GOP donor over the years. Like Reitz, these endorsers say they’re not concerned about Middleton’s legal resume — they want him for his conservative credentials.

“Mayes Middleton is one of the most conservative members in Texas Senate history — a proven, unapologetic MAGA conservative who fights and wins,” Patrick said on social media, adding that he would “make the Texas Attorney General’s office the strongest in the nation — relentlessly defending our laws and our Constitution.”

The Roy attacks

While Roy has hammered Middleton on experience, Middleton has launched a multifaceted attack on his opponent, painting him as insufficiently loyal to Trump, Paxton and conservative causes.

Roy has been a thorn in the side of GOP leadership during his tenure in Congress, undertaking often quixotic efforts to block legislation he believes unconstitutional or unduly expanding the size of government. As one example, earlier this year, he opposed a measure to criminalize the act of providing gender modification surgeries for minors over concerns about the legal framework of the bill, a decision Middleton has since thrown in his face as supporting the “transgender lobby.”

“False,” Roy said at the barbecue event, the beginning of a litany of responses to the allegations being thrown at him. “I voted for the bill in question. However, that bill is now dead in the Senate because arrogant people who don’t know about what they speak believed they could force through this bill.”

Middleton has also taken aim at Roy’s relationship with Trump, who has vacillated between calling the congressman “another ambitious guy, with no talent” to saying he’s “not easy, but he’s good.” Roy has delayed some of the president’s priority legislation over spending fights and supported Florida Gov. Ron DeSantis’ doomed 2024 presidential run against Trump. Perhaps most damning in the eyes of some conservatives, he said Trump engaged in “clearly impeachable” conduct on Jan. 6, 2021, although he later voted against impeachment.

In ads, Middleton has said Trump doesn’t trust “backstabbing D.C. Congressman Chip Roy” who “betrayed MAGA,” a theme Middleton has hammered in contrast with his “MAGA Mayes” messaging.

Roy has emphasized his near-perfect record of voting alongside the Trump agenda, and shared stories of working closely with Trump to improve legislation and carry bills on his behalf. But he’s also tried to tell voters why they want an attorney general who is willing to oppose the president — a potentially tough sell to Texas GOP voters who remain fiercely loyal to Trump.

“There’s no greater compliment that [Trump] could give me as your attorney general candidate than to say that I’m not easy, but I’m good,” Roy said. “The guy that we praise for the Art of the Deal, the guy that we think is so strong in negotiating with other countries, to say that I’m not easy, but I’m good? That’s what I want in our attorney general, whether it’s me or someone else.”

Roy has also had to battle his contentious relationship with Paxton. Roy was among the first to call for Paxton to resign after eight of his top aides reported him to the FBI for alleged abuse of office, and stood by the whistleblowers as Paxton faced impeachment. In recent days, Patrick took a swing at Roy, saying on social media that Paxton had him “escorted out of the building” when he left the attorney general’s office in 2015.

Paxton, Patrick wrote, “gave him a choice: be fired or resign. The reason was his continued insubordination to AG Paxton.”

In an interview, Roy dismissed the criticism as “people looking backwards,” and said he hoped voters would appreciate that he was public about his issues with Paxton. He noted that Middleton bankrolled two challengers to Paxton in 2022; he was also one of several senators who reportedly planned to vote to impeach Paxton but flipped when the majority wasn’t there.

Paxton, at least, seems to prefer Middleton’s quiet opposition to Roy’s more bombastic approach. According to leaked audio obtained by Texas Bullpen, Paxton said he plans to vote for Middleton and “could not imagine” Roy in the role.

The money factor

As loath as either of them are to admit it, Middleton and Roy really aren’t that different, at least when it comes to their ideological bent. Both members of the hardline Freedom Caucus in their respective chambers, both stalwart conservatives, both ambitious politicians who say they feel called by God to this role at this moment.

Who gets to answer that call will be decided May 26. In the March primary, the advantage was clear — Middleton gave his campaign almost $15 million, which he used to buy a seemingly endless drumbeat of television ads and mailers. Roy raised more than any other candidate in the race and spent $5 million on television ads, no paltry sum for a state attorney general race, but it wasn’t enough to beat the Middleton machine.

But the runoff has unfolded differently. Middleton has been slower to make television ad buys, according to media tracking firm AdImpact, giving Roy an edge on the airwaves. With early voting underway, Roy has spent more than Middleton, fueled by a surge in donations from several wealthy Texans, including $2.75 million from Amarillo billionaire Alex Fairly.

The money has helped Roy buy more television ads in recent weeks. Most of the segments hew to his original intent when he got in the race, focusing on who he is and what he’s done for Texans. But as the runoff draws closer, he’s released some new television spots, which he’s plastered across all the Texas television markets, that go negative against Middleton — criticizing him for having too many ads.