Bill O’Reilly has long helmed the most-watched show on cable news, but one prominent Republican has had harsh words for him: Gov. Jeb Bush, who once wrote that he had no respect for the host. And that tension highlights one of the ugliest stretches of Bush’s governorship.

On June 2, 2003, a Floridian named Omar Roberts—who didn’t seem to have any prior relationship with the then-governor—emailed Bush to praise him for a recent appearance on Sean Hannity’s show. Then he raised a concern: O’Reilly had been covering scandal involving Florida government entities, including the case of an autistic woman who was raped and impregnated while in state care.

“I would feel much better if you would just at least address these issues that O’Reilly is reporting either on his show or even on another interview with his friend, Sean Hannity,” continued Roberts. “I think that the issues of whether or not the Florida state leadership is to blame or if everything possible is being done—all need to be put to rest once and for all (or as much as possible).”

Then Roberts asked Bush to give him a heads-up if he ever went on the show. Bush replied to Roberts’ email a few hours later.

“Thank you for writing,” Bush said. “I did Sean’s show because he was in state and I respect him. O’Reilly on the other hand is someone who I don’t respect. I could give you many reasons but I won’t since it doesn’t matter.”

Bush then gave Roberts a little more background on the case of the autistic woman.

“Regarding the case of the woman raped, she was in a home licensed by the staten not in a state facility,” Bush continued [all typos sic]. “We revoked the license, have pushed gor a guardian for the mom and child. This is a tragic caseand we are on it. Mr. O’reilly won’t even seek information from our office on these matters. The department of children and families is a troublrf agency improving by the day. We will continue to strive to do better.”

A Bush insider told The Daily Beast that the governor gave O’Reilly a heads-up on these emails, and that the two men “have discussed and it’s water under the bridge.”

But in the early 2000s, O’Reilly leveled substantial criticism at Bush for his decision to push for two legal guardians in that case—one for the woman who was raped, and another for her fetus.

He also sharply criticized how Bush’s administration handled the case of Rilya Wilson, a young girl who disappeared from the Florida foster care system at age 4. She was gone for two years before authorities realized she was gone, and the head of the Florida Department of Children and Families resigned because of the scandal.

On a May 3, 2002, episode of his show, the host tore into the governor.

“Governor Jeb Bush says the state is reviewing the case, but the government can only go so far,” O’Reilly said. “I say baloney! The State of Florida can tell Americans exactly what happened here and arrest those responsible for criminal negligence.”

“To say they are investigating is simply a smokescreen, a Janet Reno tactic that is hollow and dishonest,” O’Reilly continued later. “Give us a status report on the investigation. Chances are that Rilya Wilson is dead because nobody cared about her. Her mother cared more about drug[s], her godmother cared more about money, and the State of Florida hired inefficient and possibly criminal people to look out for foster kids. How about a little outrage over that, Jeb Bush? How about some action?”

In a Jan. 13, 2003, segment, O’Reilly said Bush had “done a horrible job” handling the case and the department.

“We need people who take it personally, who want to help the kids,” O’Reilly said. “And with all due respect to Governor Bush, I have not seen one iota of that.”

O’Reilly also criticized Bush’s decision to push for a guardian for the fetus. The host discussed both issues in a May 20, 2003, segment, and had tough words for Bush.

“I have nothing against Jeb Bush, all right,” he said. “I don’t—you know, I know the man. I don’t have anything against him. But he just can’t seem to run the state vis-a-vis children and disabled people. This agency cannot perform. We have—this is going on six years that this has been in chaos, and I think everybody understands the situation. It’s indefensible.”

A few hours after the show aired, Jerry Regier, a social conservative activist who founded the Family Research Council, emailed Bush the text of an op-ed defending his decision to appoint a guardian for the fetus.

“I had’nt seen it and I am grateful,” Bush replied at 2:22 a.m. the next day [all typos sic]. “I got blasted on O’Reilly tonight about the rape and our inability to deal with it.”

Years later, O’Reilly has a nuanced view of Bush’s time in office. In a conversation on his show with Dana Perino on April 20 of this year, he said Bush “did a very good job in Florida.” And in March, he said he thought the former governor could beat Hillary Clinton.

But he wasn’t shy about criticizing Bush while he was in office. And that criticism seems to have hit home.