From 2000 through 2009, Donald Trump and Bill & Hillary Clinton maintained a relationship that blended business, social status, and personal networking — though never quite crystallizing into a consistent political alliance. At the turn of the millennium, Trump was already a prominent New York real estate magnate. Meanwhile, Bill and Hillary Clinton, soon after leaving the presidency, relocated to New York (Chappaqua), which brought them geographically closer to Trump’s properties. A key vector of social convergence in this period became the golf world: Trump’s private Trump National Golf Club Westchester (formerly Briar Hills) underwent major renovation and reopened in 2002. Trump later said explicitly that he had redeveloped the club in part because he believed Bill Clinton “would need a place to play.”
By May 2003, Bill Clinton officially joined Trump National Golf Club. This membership gave the former president both social proximity to Trump’s world and a regular, ostensibly apolitical venue for interaction. According to accounts, Clinton enjoyed the course: in later interviews, he said that when friends came to play with him, “that’s where I take them.” Golf during these years functioned as a “neutral ground” — neither overtly political nor purely recreational, but subtly strategic. Reports suggest that Trump and Clinton often played together. Trump has been quoted saying that after rounds, they would retreat to the clubhouse and Bill would “wax about politics” for as long as two and‑a‑half hours.
According to Bill Clinton in a 2012 Golf Digest interview, for his 65th birthday, Hillary Clinton, Chelsea Clinton, and Marc Mezvinsky (Chelsea’s husband) joined him for a round at Trump National. Clinton also noted the club’s staff were accommodating: because the birthday party was not made up of expert golfers, Trump’s people “organized all their tee times so we wouldn’t delay anybody.” Even as late as 2012, Clinton maintained a locker at Trump’s course, indicating that his membership was not just symbolic but enduring. Through golf, therefore, a consistent, though discreet, social channel existed. This channel allowed Trump access to a former president in a non‑political setting, potentially building soft influence or goodwill.
A high point of the Trump–Clinton social overlap came in January 2005, when Donald Trump married Melania Knauss. The wedding ceremony was held at the Episcopal Church of Bethesda‑by‑the‑Sea in Palm Beach, Florida, followed by an opulent reception at Mar‑a‑Lago, Trump’s private estate. Hillary Clinton sat in the front pew of the ceremony; Bill Clinton arrived at the reception. Contemporaneous reporting (e.g., People magazine) and later retrospectives note the guest list was star-studded: besides the Clintons, entertainers and media personalities like Billy Joel, Tony Bennett, Katie Couric, Matt Lauer, Heidi Klum, and more attended.
At the reception, Trump and Bill Clinton reportedly spoke about politics and golf — a mingling of personal and social capital. This wedding functioned as a public symbol of mutual respect and social acceptance. For Trump, having a former president and powerful political couple show up boosted his social legitimacy. For the Clintons, attendance affirmed their continued integration into elite, high-society circles. After the wedding, the public record shows fewer high‑visibility social events linking Trump and the Clintons. The mid-to-late 2000s were more about latent networks than overt partnership. Bill Clinton’s use of the golf course continued, but beyond that, there’s little in credible media reporting about repeated private dinners, business deals, or formal collaborations with the Trumps in that timeframe.
The Trump Foundation remained active but focused on a variety of causes; its giving was “scattershot,” rather than tightly aligned with any sustained political or philanthropic partnership. By 2007–2008, Donald Trump’s personal contributions to his foundation had declined sharply: his final personal payment was $35,000 in 2008, per the foundation’s records. A significant turning point comes in 2009. That year, the Donald J. Trump Foundation donated $100,000 to the Clinton Foundation as an “unrestricted gift.” PolitiFact confirms this donation, noting that while people (including Trump himself) sometimes phrase this as if it were a personal gift, in reality it was made via his foundation. This 2009 gift places Trump among the top 0.2% of Clinton Foundation donors by size, though in absolute terms it is modest relative to the scale of large philanthropic contributions the Clinton operation typically drew.
Notably, the foundation continued giving afterward: in 2010, it reportedly paid $10,000 to reserve a table at a Clinton Foundation gala.