Career and technical educators often attend professional development events looking for new ideas to take back to their classrooms. Mark Steedly teaches sports marketing at Winton Woods High School in Ohio as part of a satellite program of the Great Oaks Institute of Technology and Career Development, and last year he used "The Apprentice" as part of his teaching, making it a theme that continued through the school year. Steedly originally got the idea from the workshops for marketing educators that he attended in Philadelphia during the summer. Steedly used this idea and incorporated other elements that reflected the High Schools That Work goal, "to increase academic rigor and relevance to the curriculum." This article describes Steedly's process of meeting that goal by putting together his own Sports Marketing Apprentice program at Winton Woods and provides first-hand accounts from those involved. It is divided into the following sections: The Tasks; The Final Challenge; and The Winner.