“I think the key with Charles was that he was with him in 2016 and was aggressively on the cause,” said American Conservative Union Chair Matt Schlapp, a prominent Trump supporter who is also supporting Herbster. “Charles has been on the team the whole time, and not just in a small way but in a large way.”

That was not the case for the Rickettses. During the 2016 GOP primary, Ricketts’ parents, Joe and Marlene, donated $5.5 million to a super PAC devoted to stopping Trump from winning the Republican nomination. Trump lashed out, tweeting that the family “better be careful, they have a lot to hide!”

But the Ricketts family soon got on board. The day after Trump became the presumptive nominee, Pete Ricketts attended a rally in Omaha with the candidate, where the governor expressed his support. Joe Ricketts became a seven-figure donor to a pro-Trump super PAC. And after Trump won, he nominated Todd Ricketts, the governor’s younger brother, to become deputy commerce secretary. Todd Ricketts eventually withdrew his nomination but in 2018 was named Republican National Committee finance chair, with Trump personally involved in selecting him.

During Trump’s 2020 reelection race, Joe and Marlene Ricketts gave $2.5 million to the pro-Trump America First Action super PAC, putting them among the group’s biggest donors.

The 2022 governor’s contest emerged as a test of whether the Rickettses could leverage their recent alliance with Trump to stop Herbster. Nebraska Republicans trace the family’s antipathy toward Herbster back to the 2014 governor’s race, when Herbster financed a Pete Ricketts opponent, Beau McCoy. The race got personal, with McCoy calling Ricketts a hypocrite for co-owning what McCoy described as the “gay-friendly” Chicago Cubs — an apparent reference to Ricketts’ sister, Laura, who is a lesbian. (Herbster has said he didn’t agree with McCoy’s criticism and denied that he had anything to do with it.)

The two squared off again in 2020, when Herbster, who owes his fortune in part to selling bull semen, bankrolled a state legislative candidate who waged a primary challenge against a Ricketts-appointed officeholder. The Ricketts-backed contender, Julie Slama, ultimately survived the hard-fought contest, but the governor’s orbit remembered Herbster’s involvement.

Tensions quickly boiled over as the 2022 governor’s race got underway. After Herbster launched his campaign this spring, the term-limited governor publicly came out in opposition. Meanwhile, a top Ricketts political adviser, Jessica Flanagain, took a job with a Herbster primary opponent, Jim Pillen, leading to speculation that the governor was picking sides in the primary.

But the most dramatic turn came two months later, in late June, when Ricketts attended an RNC-hosted donor retreat at the Ritz-Carlton Resort in Dana Point, Calif.

After delivering a headline speech, the governor ran into Kellyanne Conway, a former Trump adviser who is working for Herbster. A heated exchange over the Nebraska race ensued.

According to a person familiar with the interaction, Conway approached Ricketts and complimented him on his remarks and his education policies. She also mentioned that she and the governor would be on different sides of the race to succeed him.

Conway — who has previously worked with the Ricketts family on political projects and, during the 2016 election, set up a meeting between the Ricketts family and Trump — later relayed to others that she was surprised by what she described as Pete Ricketts’ aggressive tone and vitriol toward Herbster during the conversation.

“What I thought was a polite acknowledgement quickly devolved into what I realize was not a philosophical or political difference with Gov. Ricketts toward Charles Herbster, but rather a personal one,” Conway said in a statement.

She added: “While I won’t disclose details of a private conversation, I was shocked because I have long respected the Ricketts family and helped broker the peace between Joe Ricketts, Todd Ricketts, and Donald Trump in the fall of 2016, inviting them to the private residence in Trump Tower.”

A Ricketts spokesperson, Corben Waldron, said that the governor “has no personal issue at all” with Herbster, but acknowledged that Ricketts “in an honest and pointed conversation did outline multiple reasons why he believes Herbster is ill-suited to be governor of Nebraska.” Ricketts has accused Herbster of, among other things, shipping jobs out of state through his company, a charge Herbster has denied.

The bad blood persisted. A week later, on July 2, Herbster met with Ricketts at the governor’s mansion — a moment that could have thawed the relationship. Instead, two people familiar with the sit-down described it as tense and abrupt, lasting a mere six minutes. Herbster had requested the meeting months earlier, and upon sitting down was asked by Ricketts what he wanted to discuss. Herbster talked about his campaign and insisted his goal hadn’t been to hurt Ricketts in the 2014 race. The governor tersely thanked Herbster for coming in, and the meeting was over.

It was around that time that Ricketts phoned Trump and asked him not to endorse Herbster. As he pondered what to do, the former president began asking senior Republicans how the Ricketts family’s and Herbster’s donation records stacked up against each other.

In mid-October, Trump called Todd Ricketts to ask for his opinion. Ricketts, who as an RNC official is reluctant to explicitly take sides in primaries, urged the former president to remain neutral for the time being, according to two people familiar with the discussion. The younger Ricketts argued that the field of candidates could still grow, pointing out that former GOP Gov. Dave Heineman may launch a comeback bid.

“Todd loves his brother Gov. Ricketts and respects President Trump, but as RNC finance chairman he stays out of Republican primaries,” a Todd Ricketts spokesperson said.

Within Nebraska Republican circles, speculation swirled that the Rickettses had quashed any prospect that Trump would endorse Herbster.

But in October, Herbster and Conway quietly ventured to Trump’s Mar-a-Lago estate in South Florida to meet with the former president. Those familiar with the sit-down said it stretched on for several hours and ultimately sealed Trump’s decision to endorse the candidate. Conway, who was Trump’s 2016 campaign manager, was regarded as instrumental in swaying Trump’s decision.

Those in the Ricketts camp say they never dismissed the possibility that Trump could endorse Herbster, but they were still taken aback. A few hours after Trump made his announcement supporting Herbster, the governor released a statement saying that “while I agree with President Trump on many things, I strongly disagree that Charles Herbster is qualified to be our next governor.”

The next day, Herbster fired back with a statement of his own, going after Ricketts for his family’s past opposition to Trump and savaging the governor for “personally attacking me and President Trump’s endorsement.”

Trump has privately stood by his endorsement. During a conversation with advisers a few days after his announcement, the former president spoke about how Pillen, the Herbster primary rival who is widely perceived to be a Ricketts favorite, didn’t vote for him in the 2016 presidential primary.

“It’s not as bad as voting for Hillary, but he wasn’t with me,” one person with direct knowledge of the conversation quoted Trump as saying.

(Pillen has said he voted for Trump in the 2016 and 2020 general elections.)

Nebraska Republicans predict that Trump’s endorsement could play a major role in the primary and vault Herbster into serious contention. The former president, who won Nebraska by nearly 20 points in 2020, remains a popular figure in the state.

But Ricketts may not be done yet. The governor and his family have a long history of investing in Nebraska’s political battles, and they could spend heavily in the hope of preventing Herbster from winning the nomination.

“They’ve always been able to support financially candidates of their choice,” said former Nebraska GOP Rep. Hal Daub. “Certainly, if the family decided to weigh in financially on the race, I think that would be influential.”