Robert Richard Titcomb, 49, allegedly met an officer posing as an escort from an online service, and offered to pay $100 for sex, according to police.
Hawaii News Now reports that Titcomb and Obama have been "close friends since their childhood days at Punahou School."
The two are frequently seen on the news golfing, playing basketball and dining together when the Obama family vacations in Hawaii.
As CNN points out, the Obama family spent time with the Titcombs this past December and January. White House pool reports from the period identify Titcomb by name. Obama golfed with Titcomb on December 23, December 26, December 28 and January 2.
Titcom, who was released after posting $500 bail, is scheduled to appear in Honolulu District Court on May 2.