The club had its origins around 1895, with Briarcliff founder
Walter W. Law's private nine-hole course on his estate, which became available to
Briarcliff Lodge guests, and was then known as the Briarcliff Golf Club. In 1922, Devereux Emmet designed a course across the street with eighteen holes, and thus Briarcliff Country Club was founded that year. The discussion between the Trump Organization and village government stopped that year, however in 2004, Trump submitted a new request to bring a LPGA or
PGA tournament to the club. (The Sybase Classic would eventually be moved to
Upper Montclair Country Club in New Jersey before its cancellation after the 2009 playing.) A storm in June 2011 caused public utilities including the Briarcliff library and Law Memorial Park's public pool and playing fields to be flooded. When Trump had renovated the course, his workers made unauthorized changes to its drainage system, which made the course look and play better for golfers. The alterations lowered the system's water capacity and thus raised water levels by about six feet. The Trump Organization met with the village over the issue, though it did not take corrective actions. After negotiations ended, the village billed the club $238,353. The Trump Organization blamed the flooding on a village drainage pipe which lacked a grate, and blamed the conflict on then-Briarcliff mayor William Vescio, who owns a company that previously came into conflict with Trump. Vescio denied the relation to the previous conflict and claimed that the flooding was caused by rocks and trees at washed down the hill from the golf club. Trump's candidacy for the
2016 United States presidential election affected the club;
Horace Greeley High School used the facility for its annual proms, which was protested by its students in late 2015 due to its connection to Trump as a political candidate. The graduating class voted, 97–44, to keep the venue. On June 7, 2016, Trump gave his nomination victory speech at the clubhouse; he had just won the
Republican primaries. In July 2016, during Trump's presidential campaign, his opponent
Hillary Clinton released a campaign video of one of the club's architects. The architect, Andrew Tesoro, described his dealings with
the Trump Organization, where about a dozen employees met him at the finished clubhouse to negotiate reducing his fees. They pressured him into sending a reduced bill, of $50,000 instead of $140,000. After the organization failed to pay the bill, Tesoro met with Trump who convinced him to accept only $25,000 for his services. The
Clinton campaign used the story as part of its effort to demonstrate that the Trump Organization harms small businesses. Later during Trump's campaign, in September 2016,
The Washington Post reported that a painting of Trump may be on display at the club. Trump had purchased Michael Israel's work for $200,000 in 2007 through his charity, the
Donald J. Trump Foundation. According to IRS regulations, the painting would have to be used for a charitable purpose, or donated to a charity, however Melania Trump had planned to hang it in the club's boardroom or conference room, and the artist later stated he believed it was at the clubhouse. Although the painting was purchased at a charity auction, where half of the Trump Foundation's check went to the charity, in September 2016 an IRS director deemed Trump to have violated IRS rules and President
Barack Obama publicly criticized Trump's purchase. The golf club was a topic of discussion in 2019, in a trial against the now-defunct Trump Foundation, where the president admitted the foundation had been used to settle legal obligations of the club. ==Current operations==