WASHINGTON — Well before Hillary Clinton called Donald Trump a politician “trafficking in prejudice and paranoia,” there were decades of amiability. She posed, grinning widely, for a photograph with him and two of his sons. He was on the White House Christmas list. They would cross paths at glittering New York parties. She attended his wedding reception.
The early phases of that respectful, if not especially close, relationship were detailed in a trove of papers released Tuesday by the William J. Clinton Presidential Library.
Even after the Clintons left Washington and settled in New York to build their charitable foundation and her own political career, Trump and the Clintons coexisted perfectly reasonably. For a time, at least, they mutually benefited from exposure to one another’s worlds.
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The relationship appeared far more rooted in work than pleasure. Trump enjoyed the buzz of attending the same glittery events as the powerhouse political stars. He also poured money into the Clinton charitable operation and donated modestly to Hillary Clinton’s campaigns.
“The Trumps don’t really socialize very much,” said David Columbia, who runs New York Social Diary, a website that tracks the social lives of the city’s famous residents and has never seen the Clintons and Trumps together.
“The Clintons are the same thing. They really aren’t social. Everything they do that is social has something to do with their business, which is politics.”
“He’s all business,” Columbia said. “She’s all business, too.”
Still, Hillary Clinton engaged in some humor at the real estate magnate’s expense: Back in January 2000 as Hillary Clinton was running for US Senate, she appeared on “Late Night with David Letterman” and offered the top 10 reasons why she agreed to go on the show: No. 5 was “I needed an excuse to get out of dinner with Donald Trump.”
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Trump’s posture toward Clinton, at least publicly, was more gracious.
“The First Lady is a wonderful woman who has handled pressure incredibly well,” wrote Donald Trump in the introduction to his 1997 book ‘The Art of the Comeback.’”
That was the caption of a photograph showing Hillary Clinton grinning and standing between Trump and his sons Donald and Eric. Photographer Sarah Merians recalled little about the undated picture -- only that Trump had arranged for it to be taken.
Much has been made about a different photo, the now iconic image of the two couples grinning together and looking glamorous at Trump’s third wedding reception, after he married Melania, held in his Mar-a-Lago estate.
Clinton has said she attended because she “thought it would be fun to go” and “it’s always entertaining.”
But last year when questioned at an event in Iowa, she said she gave the Trumps “nothing” as a wedding gift.
And she’s noted that she went because she’d planned to be in Florida that same January 2005 weekend anyway. In fact, it’s not even clear that Hillary Clinton attended the actual wedding ceremony — the New York Post reported that the Clintons skipped the vows to attend a nearby surprise party for Boston Bruins owner Jeremy Jacobs.
Trump has said “it was very nice” that the Clintons came, and indicated that they had to be there because of all of the money he’d pumped into Clinton Inc. He has donated between $100,000 and $250,000 to the Clinton Foundation.
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However, Trump never showed up to the organization’s glittering Clinton Global Initiative gatherings in New York, according to a Clinton spokesman.
He also donated, on a much smaller scale, to Clinton’s Senate campaigns and her first presidential run. That totaled about just over $3,000.
“I know Hillary very well. In fact, her and her husband, who’s a terrific guy, have a house right next to my golf club up in Westchester,” Trump said in a quote reported by Hotline in December 2006.
Even as Clinton was preparing her first run for president, relations between the Trumps and the Clintons remained cordial:
“I really have enjoyed the time I have spent with Hillary,” Marla Maples, then Trump’s wife, wrote in a January 2007 e-mail addressed to her “sweet friends” urging them to support Clinton.
“She is very clear, very focused, and I feel we will at last have a voice and be received with a welcoming and open ear.”
But, despite the effusive praise, there’s little evidence that the couples spent considerable time together when in Manhattan. Yes, they were “spotted” or named as invitees to a number of the same events, but the hosts didn’t recall seeing them together or declined to comment.
One friend close to Clinton, who didn’t want to be named, said that the two couples occupied very different cliques in New York. An event attended by both Hillary Clinton and Donald Trump meant its appeal was so broad that every celebrity was going — that the crème of different tribes were mingling together.
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The Clintons and the Trumps shared some common friends — though many seem to be siding with Clinton over Trump in the 2016 contest.
Television personality Star Jones, for example, was close enough to both to invite them to her 2005 wedding. But now her Twitter feed is full of observations supporting Clinton and deriding Trump. “This #Trump #Cruz #whoseIsBigger fight is dirty tacky & unworthy of being #POTUS. Water seeks its own level . . . ,” Jones posted on her Twitter feed on March 25.
Bill Clinton and Trump also crossed paths from time to time in matters that did not involve social events.
The former president, a golf enthusiast, joined the Trump National Golf Course, which is near the couple’s home in Chappaqua. A spokeswoman for Clinton declined to say if the former president is still a member.
Clinton was spotted considering buying a pied-a-terre in Trump Riverside, one of Trump’s buildings, according to a 2005 article in the New York Daily News. Clinton’s spokesman at the time denied the account, but the paper quoted a “friend” of Clinton’s as saying the former president “may have looked at floor plans.”
The Clinton world, however, closely watched what Trump was saying and doing — even when his toehold in politics was ignored by most.
Filmmaker Harvey Weinstein bragged in a 2012 e-mail sent to then secretary of state Hillary Clinton that he’d “talked about how Donald Trump was uncool” during a 2012 interview with CNN’s Piers Morgan.
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But examples came much earlier, according to the nearly 500 pages of documents, most unsubstantial, released by the Clinton Library Tuesday. In 1999, White House spokesman Richard Siewert forwarded to other White House aides a news story about Trump’s proposal to tax the rich.
“We may need some guidance on this,” wrote Siewert, who now works at Goldman Sachs, in the subject line.
But another round of debate came over a question with far less substance: Should the president of the United States acknowledge Trump’s 50th birthday?
“What are you [sic] thoughts on sending a birthday letter to Donald Trump — who turns 50 on June 14?” asked Betty Currie, Clinton’s personal secretary, in an e-mail to White House deputy political director Karen Hancox four days before the birthday.
Several days later Currie had an answer: “Cancel letter to Donald Trump. Let me know,” she wrote to an underling who had been assigned the task.
Annie Linskey can be reached at annie.linskey@globe.com. Follow her on Twitter @annielinskey.