The Squires were established under the direction of Brother Barnabas McDonald, F.S.C. together with Supreme Director Daniel A. Tobin on August 4, 1925. At that time there was a national interest in youth in the United States, as reflected by the development of the Boy Scouts of America and the Big Brother movement.

Each Circle is supervised by a Knights of Columbus Council or Assembly and has an advisory board made up of either the Grand Knight, the Deputy Grand Knight and Chaplain or the Faithful Navigator, the Faithful Captain and Faithful Friar. Circles are either Council based, parish based, or school based, depending on the location of the circle and the Knight counselors.