Donald Trump and former Florida Governor Jeb Bush are trading insults on the campaign trail. Here’s a few of their best sparring moments. (Pamela Kirkland/The Washington Post)

Donald Trump spent a day in January 2014 hobnobbing with politicians at the Trump International Golf Club in West Palm Beach, Fla. The billionaire mogul touted legalizing gambling with state Rep. Steve Crisafulli, speaker of the Florida House, and two other wired Florida Republicans, plugging his properties as potential sites for casinos.

But as they tapped putts on the manicured greens, something else was on Trump’s mind: Jeb Bush.

“He was trashing Jeb and, quite honestly, I don’t think he’s ever held Jeb in high regard,” said Crisafulli, a Bush supporter who said he was “uncomfortable” with the conversation and defended the former Florida governor to Trump. “I’ve met with Mr. Trump on several occasions, and he’s constantly had things to say about Jeb. . . . He’s always had a negative connotation about Jeb.”

Trump’s jeering that day was a harbinger of the taunts and derision that the 2016 GOP front-runner has directed at Bush on the campaign trail this summer.

The feud between the leading Republicans, which has escalated in recent days, is shaping up as a defining dynamic at this early stage of the race. And considering Trump’s dominant status in polls and Bush’s fundraising ability, the tensions between the two are likely to be a factor for weeks or months to come as each candidate attempts to topple the other on his way to the nomination.

The 2016 campaign is only the latest manifestation of decades of discord between Trump and the Bush family. Since the gilded 1980s, when Trump and George H.W. Bush rose as forces in their respective spheres, the relationship between Trump and the Bushes has been a melodrama — veering between displays of public affection and acerbic insults.

At the core, there are clashes of style, manner and class between the Bushes — a patrician clan of presidents, governors and financiers who have pulled the levers of power for generations — and Trump, a hustling New York City deal-maker who turned his father’s outer-borough real estate portfolio into a gold-plated empire.

“The Bushes were never Trump’s cup of tea,” said Roger Stone, a longtime confidant and former adviser to Trump. Asked why the Bushes often have kept Trump at arm’s length, he said: “He’s not from old, WASP money. The Trumps didn’t come on the Mayflower.”

‘He’s not up to snuff’

Trump shrugs off the suggestion that his rivalry with the Bushes is rooted in pedigree, although he is open about his animosity toward them; he characterizes his relationship with former president Bill Clinton, for instance, as far closer.

He lashed out at former president George W. Bush over the war in Iraq during his tenure. He turned on Bush’s father when he raised taxes during his term as president, despite pledging not to do so.

But Trump reserves particular, personal ire for Jeb Bush, whose first name he commonly mocks by drawing it out in a slight drawl. One Trump associate, who spoke on the condition of anonymity in order to speak candidly, said of Trump: “He’s very smart, he’s driven and he has two goals: one, to be elected president, and two, to have Jeb not be president.”

In a 35-minute interview this week with The Washington Post tracing his history with the Bushes, Trump unleashed a hailstorm of scorn. He found 33 ways to skewer the family — about one put-down per minute.

On Jeb Bush: “I mean, this guy. I don’t think he has a clue.”

On George H.W. Bush: “I really liked the father — really like him as a person. But I hated his ‘read my lips, no more taxes,’ and then he raised taxes monstrously.”

On George W. Bush: “He didn’t seem smart. I’d watch him in interviews and I’d look at people and ask, ‘Do you think he understands the question?’ ”

And back to Jeb: “He’s not up to snuff. . . . Jeb is never going to bring us to the promised land. He can’t.”

Trump was especially accusatory when he talked about Jeb Bush’s work in investment banking. After leaving the governor’s office in 2007, Bush was an adviser to Lehman Brothers and, later, Barclays, making between $1.3 million and $2 million a year. Trump called Bush’s role at Lehman a “no-show job” and suggested it was a reward for helping direct Florida state funds to the firm, whose collapse in 2008 helped kick off the Great Recession.

“That’s a Hillary Clinton kind of situation,” Trump said, referring to the Democratic front-
runner. “This is huge. Let me ask you: Why would you pay a man $1.3 million a year for a no-show job at Lehman Brothers — which, when it failed, almost took the world with it?”

Asked whether he thought Bush was ready to steer the nation’s economy, Trump said, “Steer it? He can’t steer himself.”

‘Liberal cocktail parties’

Tim Miller, a Bush spokesman, said Trump “is trafficking in false conspiracy theories” about Lehman.

Responding to Trump’s broader criticisms, Miller highlighted the developer’s past ties to Democrats and liberal causes.

“While Trump was attending New York liberal cocktail parties and trashing conservatives and Republican presidents any chance he got, Jeb was the most conservative governor in the country, cutting taxes, reining in the size of government and protecting life,” Miller said.

In Florida, Bush’s associates have been flummoxed by the pace and intensity of Trump’s assaults. Former governor Bob Martinez, a Bush friend and supporter, asked, “Is this the way he acts when he’s negotiating with somebody?”

“Some find it entertaining, some find it odd,” Martinez said. “This is not the normal fare you get, certainly.”

Bush has begun firing back on the stump, though not with Trump’s vigor and mostly without naming his opponent. “There are some people running, they’re really talented about filling space — about saying big things,” he said Wednesday in Pensacola, Fla. “They think that volume in their language is a kind of a version of leadership. Talking is not leadership. Doing is leadership.”

Al Cardenas, another Bush friend, suggested Trump’s motivation is pure politics: “He wants to win this thing, he sees Jeb as the big gorilla with the big super-PAC money and someone who would eventually be the one facing him in the homestretch.”

Cardenas also surmised that Trump had been a non-factor in Bush’s mind.

“In a thousand conversations I’ve ever had with Jeb, I’ve never heard Donald Trump mentioned once until last year,” Cardenas said. “He was just not a part of ‘Jeb world’ in any way that I recall.”

Jeb Bush ‘a good man’

Trump fondly remembers one of his first encounters with the Bush family patriarch. It was 1988, and he hosted George H.W. Bush for a presidential campaign fundraiser at the Plaza Hotel, the palatial New York property Trump owned at the time.

“I remember Don King was there,” Trump said in the interview. “Big Don King. . . . He’s shaking Bush’s hand and saying, ‘Only in America!’ And, you know Don King’s voice. It’s like Pavarotti, right?”

Trump soured on Bush when he increased taxes, but they eventually made amends. In 1997, Trump said, Bush asked him to host a fundraiser for his son, Jeb, who was running for Florida governor. Trump agreed. The event was in his apartment at Trump Tower.

It was not merely a political favor. Trump had been trying to persuade Florida lawmakers to allow his company to manage casinos on tribal land.

“I had a fundraiser and raised about $1 million, which in those days was a lot of money,” Trump said. “In fact, I remember [Jeb Bush] saying, ‘It was the most successful fundraiser I’ve ever had.’ ”

Trump said George H.W. Bush wrote him “a beautiful note thanking me for helping with his son.”

Nevertheless, Trump’s swipes at the elder Bush continued and extended onto the pages of his 2000 book, “The America We Deserve.” In it, he said the 41st president “failed to comprehend that he was in the bubble created by the American presidency and simply lost touch.”

In that same book, Trump praised Jeb Bush as a “good man” who is “exactly the kind of political leader this country needs now and will very much need in the future. . . . I believe we could get another president from the Bushes.”

Trump’s unpredictable commentary led most Bush insiders to keep their distance. Nicholas F. Brady, a family intimate and former treasury secretary, said in an interview that the Bush circle has rarely overlapped with Trump, politically and socially.

As for the pot shots at Jeb these days, Brady said, “He must understand that Donald’s way of expressing himself is different. He tends to short-hop problems and that’s his style. We can’t do much about that.”

Former ambassador Mel Sembler, a Bush family friend and fundraiser, said he attended the 1997 event at Trump Tower and suggested that the current animus must be “newfound.”

“You don’t have animosity toward somebody and then put on a fundraiser in your home,” Sembler said. “I would never put on a fundraiser — and I put on an awful lot of them — unless it was somebody I really felt like would be a great political leader.”

‘I have never tried to click’

In 1999, as then-Texas Gov. George W. Bush was consolidating the Republican establishment behind his 2000 presidential candidacy, Trump explored a run of his own in the Reform Party, which grew out of the 1992 independent run of Ross Perot that many Republicans were convinced cost Bush’s father his reelection.

Trump went on CNN’s “Larry King Live” and said Bush had not been forthcoming enough about his problems with alcohol. Later that fall, Trump made a splashy visit to Miami, Jeb Bush’s adopted home town. Rallying Cuban Americans in Little Havana, Trump knocked George W. Bush and then-Vice President Al Gore by saying that his wealth made him more qualified to be president than the two descendants of politicians because they were, as he put it, “anointed.”

In the end, Trump did not run. But by George W. Bush’s second term in the Oval Office, Trump had become a thorn in the president’s side. In the run-up to Bush’s 2004 reelection, Trump criticized his management of the Iraq war. By 2007, he declared that Bush was “a horrible president — possibly the worst in the history of this country.”

Trump said in the Post interview that he blames Bush for the rise of the Islamic State terrorist group, which has seized parts of Iraq and neighboring Syria.

“I was very much opposed to the war in Iraq,” he said. “The brother went in and destabilized the entire region. If [Jeb’s] brother didn’t do that with Iraq, I don’t think you’d have a destabilized Middle East right now.”

During Jeb Bush’s two terms as governor, even as his business interests expanded in South Florida, Trump shunned him.

“I’ve never tried to click,” he said. “If I devoted time to being friendly with them, don’t you think I’d be friendly with them?”

Instead, Trump cultivated ties to Bush allies in Tallahassee, inviting them to play golf or to dine with him in Manhattan or South Florida.

Recounting one outing with former state House speaker Will Weatherford (R), Trump said: “I think they were more impressed with my golf game than anything else, if you want to know the truth. . . . I shot 72.”

Weatherford said this week that he did not remember Trump shooting 72.

“Mr. Trump seems to always have an optimistic view of his abilities,” Weatherford wrote in an e-mail. “I respect him and his candidacy, but I am a Jeb Bush supporter like most current and former public officials in Florida.”

Ed O’Keefe in Pensacola, Fla., contributed to this report.