Trump is fixated on Ron DeSantis' disloyalty. Jeb Bush saw what it was like to be upstaged by a protégé.

• Trump calls DeSantis "disloyal" as he seems to be mounting a challenge for the 2024 nomination.
• The dynamics are similar to 2016, when Sen. Marco Rubio and Jeb Bush were in the arena together.
• Insider dove into the similarities and differences between the duos. 

Donald Trump needs loyalty.

His Oval Office command to FBI Director James Comey became one of the defining moments of his presidency. Rejected by the American people in 2020, Trump lashed out at lawyers, Cabinet secretaries, and ultimately his vice president who had stuck with him through his chaotic term but wouldn't support his unconstitutional effort to cling to power.

It is then fitting that the characteristic the former president says he prizes the most is already defining the 2024 Republican presidential nomination fight. One former Cabinet secretary, former UN Ambassador Nikki Haley, is opposing the former president. Another, former Secretary of State Mike Pompeo, is openly flirting with a run. So is former Vice President Mike Pence, who, in Trump's eyes, may have committed the most disloyal act imaginable.

None of them has the story of Florida Gov. Ron DeSantis. Few Republicans tied their primary fortunes to Trump in the way the now two-term governor did. Trump is already fuming about the perceived betrayal, even though DeSantis has yet to formalize his intentions for 2024. Trump's team is even branding DeSantis as "the apprentice," a nod to the reality TV show where Trump once aimed to crown his next business consigliere.

While Trump has been more open than most about how he sees the rivalry, he isn't the first politician living in Florida to go through this.

Eight years ago, former Florida Gov. Jeb Bush found himself in a similar place. Like Trump, Bush has experienced what it's like to watch a younger man overshadow him, a man he worked hard to support. 

For Bush, that man was US Sen. Marco Rubio. 

Bush and Rubio were allies in Florida government, and Rubio was widely viewed as a Bush protége. Then, when both were in the ring for the 2016 Republican presidential nomination and Rubio outshined Bush, a complicated dynamic unfolded.

"It's not at all unusual for former allies to run against each other in presidential primaries — it happens virtually every cycle," Alex Conant, a founding partner at Firehouse strategies who was communications director for Rubio's 2016 presidential campaign, said. "There's no reason to think ambitious young politicians will 'wait their turn.'" 

To be sure, Rubio and Bush had a far warmer relationship than Trump and DeSantis. Also, Conant said Bush and Rubio attracted different primary voters, while operatives view Trump and DeSantis as being in the same "lane." But today, just like in 2016, both Florida men appear to have a path to the nomination. 

And despite differences, the underlying cliché is still stands: The student is becoming the master.

"It does feel like some archetypal plot lines are happening," Miami Beach Mayor Dan Gelber, who was the top Democrat in the Florida Senate when Bush was governor, told Insider. "It's almost Oedipal," he added, referring to the Greek tragedy in which a king unwittingly kills his father and marries his mother.  

A tale of two alliances

Two decades ago, Bush was the leader of the Republican movement in Florida, spearheading school vouchers and fiscal conservatism. Rubio was a "lieutenant in Jeb's Army," skilled at articulating his positions, Gelber said.

When Rubio became Florida's House speaker in 2005, Bush handed him a gold and silver sword and extolled him as a "great conservative warrior." Rubio, then 34, made history as the first Cuban American to lead Florida's lower chamber, and Bush said he was ready for the next generation of leaders. 

"To me it was beyond literal," Peter Schorsch, a former GOP political operative who's now the publisher of FloridaPolitics.com, told Insider. "It was King Arthur giving over a weapon to Lancelot. That was just the defining picture of that relationship."

Bush encouraged Rubio to run for the US Senate and attended his victory party. When Mitt Romney was the 2012 GOP presidential nominee, Bush urged him to pick Rubio as his running mate. He told PBS he had a "close relationship" with Rubio and admired him. 

Despite this, Gelber told Insider he didn't think that either men believed Bush had been responsible for Rubio's ascent. "Jeb created a movement in Florida that Marco clearly was important in, and rose to prominence in, but you could say that about every Republican from 20 years ago who rose to prominence in Florida," he said. 

In contrast, the DeSantis-Trump alliance was more about political convenience, David Kochel, owner of Redwave Communications who was senior strategist on Bush's presidential campaign, said. 

"Jeb was much more of a mentor to Marco than Trump ever was to DeSantis," he said. "But that said, DeSantis definitely took advantage of Trump's standing within the primary electorate to help him." 

When Trump was in the White House and DeSantis was a congressman, he frequently defended the president on Fox News over the Russia investigation. When DeSantis decided to run for governor, he wanted Trump's support. 

In his book "The Courage to Be Free," DeSantis discloses little about the endorsement conversation with Trump. He credits the president for raising his name recognition, but then writes that a debate performance got him the GOP nomination against his better-known challenger. He also suggests Trump's name was a liability in the general election. 

Trump, for his part, describes DeSantis as having "begged" for his support, telling radio host Hugh Hewitt in February that the young, little-known congressman had tears in his eyes — a questionable account given that DeSantis is known for stoicism.

Still, polling at the time showed that Trump's backing gave DeSantis a significant boost, and the president would go on to host numerous rallies for him. DeSantis ran a Trump-centric campaign that included a viral ad where he was teaching his children about Trumpism. 

"I can't think of a candidate in this country who has leaned in more to the presidential endorsement than Ron DeSantis," White House counselor Kellyanne Conway said on Fox and Friends in August 2018.

When DeSantis became governor, he attended several events with Trump. Today, many political insiders still view DeSantis as Trumpian or working off the former president's playbook, pointing to examples such as his political stunt of flying migrants to Marthat's Vineyard.

"Trump was a cult of personality, and Jeb was a cult of policy," Gelber said. 

Rubio shrugged when Insider asked his thoughts about the changing-of-the-guard themes bubbling up now, in regards to Trump and DeSantis, and how that compared to 2016. "I haven't even analyzed it," he told Insider.

Bush, through a representative, declined Insider's request for an interview, and the DeSantis team didn't respond to a request for comment. 

"President Trump's endorsement is the single, most power tool in political history and his America First movement has led to overwhelming victories across the country," Steven Cheung, Trump's campaign spokesman, told Insider "He received over 5.6 million votes in Florida alone in 2020, more than any other candidate or politician in the state's history. There is nobody who can even come close to generating the excitement and enthusiasm as President Trump has and will do in 2024."

Fallout from presidential runs 

As member of the first family of Republican politics, Bush was an early big-dollar donor favorite in 2016. The political world readied for a showdown between two establishment candidates: Bush and former Secretary of State Hillary Clinton.

In the end, Trump branding Bush as "low energy" wasn't the only thing standing between Bush and the nomination. The other was Rubio, who proved to be the better campaigner. 

It would be a bitter fight. Bush's team homed in on Rubio's missed votes. During a CNN town hall, Bush portrayed Rubio's youth as a vulnerability and called him a follower of his in Tallahassee.  

Rubio hit back hard during a debate: "Someone has convinced you that attacking me is going to help you."

Neither Rubio nor Bush would win the 2016 primary. The strategic misstep was that all the GOP candidates were attacking each other instead of Trump, Kochel said. 

"Somebody had to go take out Trump and nobody made the decision to do that because the consensus view — including in pundit class and media — was that Trump was going to blow himself up at some point," Kochel said. 

Assuming DeSantis formally gets into the race, the Trump-DeSantis rivalry is considered to be one of the most closely watched storylines for 2024. 

The breakage started between the two men after Trump left the White House. DeSantis gained the spotlight on his own, initially through bucking federal health advice on COVID-19 mitigation policies. By late 2021, articles citing anonymous sources began leaking that Trump was annoyed with DeSantis.

The governor didn't seek Trump's endorsement for his reelection bid, and Trump nicknamed him "Ron DeSanctimonious." The back and forth has been heated since.

"No one has mastered the Trump relationship better than Ron DeSantis," said Schorsch, who supported DeSantis' Democratic challenger in the 2022 reelection race. "DeSantis is like the one person who has gotten more out of Trump than Trump has gotten out of them."

Sam Nunberg, a former Trump 2016 campaign advisor who had a public falling out with Trump, laughed at the position the former president now finds himself in.

"Think about another time in Donald Trump's career when somebody in business that he really helped then outshined him, or in entertainment that he promoted or he brought up — then that person competed against him in the same arena and beat him," Nunberg told Insider. "Trump has always been the king of his own domain and the stage that he's put himself in."