Intercollegiate athletics have become an integral part of campus life (Denhart, Villwock, & Vedder, 2010; Mixon & Trevino, 2005; Shulman & Bowen, 2001), and have grown exponentially in the resources universities put forth to participate in this extracurricular activity (Clotfelter, 2011). One of the biggest evolutions of intercollegiate athletics has been the collegiate athlete transfer phenomenon (Cooper & Hawkins, 2014); however, little research has been conducted on transfer collegiate athletes, or the transfer collegiate athlete experience. As such, the purpose of this instrumental case study was to discover and describe the experiences and perceptions of swirling-transfer collegiate athletes at Athletic State University. A purposive sample included nine collegiate athletes (six football and three baseball) interviewed and observed to gain a holistic experience of the swirling-transfer phenomenon, with multiple supporting documents also collected and analyzed. Participants of this study describe this unique experience as “the roller coaster experience”. Each collegiate athlete perceives their participation in athletics and higher education as a means for social mobility and intends to pursue professional league opportunities. Recommendations to intercollegiate athletic governing associations, institutions, and scholars are included, with an emphasis of creating a database to track this subpopulation of transfer collegiate athletes, as well as educating practitioners who support these collegiate athletes every day.