“It was a quiet donation that came with a simple cover letter,” Smith said. It read: “Great meeting with you and your wife in my office,” dated May 6, 2011. Enclosed was a check for $10,000 from the Donald J. Trump Foundation.

That check is one of at least several donations to suggest Trump used his private foundation, funded by outside donors, to launch and fuel his political ambitions. Such contributions, if they were made solely for Trump’s benefit, could violate federal self-dealing laws for private foundations.

From 2011 through 2014, Trump harnessed his eponymous foundation to send at least $286,000 to influential conservative or policy groups, a RealClearPolitics review of the foundation’s tax filings found. In many cases, this flow of money corresponded to prime speaking slots or endorsements that aided Trump as he sought to recast himself as a plausible Republican candidate for president.

Although sources familiar with the thinking behind the donations cautioned that Trump did not explicitly ask for favors in return for the money, they said the contributions were part of a deliberate effort by Trump to ingratiate himself with influential conservatives and brighten his political prospects.