In the Fall of 2000, the Foundation announced its first round of grants, and gave away $500,000 to Floyd County not-for-profits. In spring 2002, the Foundation decided to give $100,000 in scholarships for the post-secondary education of Floyd County Students. That fall, the Foundation's board made a commitment to a major community initiative by committing $1 million a year for twenty years to the Scribner Place-YMCA project. The first check for $1 million was given in January, 2003.

The following spring in 2003, the Board decided to award four-year scholarships to students to encourage them to continue their education and complete a college degree or vocational certification. The value of the scholarships awarded will be $400,000 over the course of the students' education.

The body of the Foundation's assets derived from a contribution agreement with Caesars Indiana. The Riverboat Casino makes monthly contributions to the foundation based on a percentage of casino revenues.  The income is used for both direct grant making and to build the foundation endowment.

In 2008 the Caesars Foundation was rebranded as the Horseshoe Foundation of
Floyd County