Gary Naylor Jr. was hired by the Long Island Railroad in 2001, and in 2006, he was initiated as a Machinist at Long Island Railroad Local Lodge 754. Naylor served as a Committeeman, Shop Steward, Local Chairman, and Vice President. In 2013, Naylor was appointed as a General Chairperson for District Lodge 19, where he negotiated contracts for members at Metro-North Railroad, Pan AM Railway, and Long Island Railroad. In December 2019, Naylor was appointed as a Special Representative to the Air Transport Territory and later elevated to Grand Lodge Representative.