Troy's letterman jacket was worn by him in his freshmen year at Greendale Community College. He wore it during his first few weeks at school and it was considered a signature item of his much like Shirley's purse was to her, or Jeff's cell phone was to him. It was gray with black sleeves and a large purple "R" embroidered over the left breast of the jacket. The clothing served as a reminder of his previous life at Riverside High when he was the school's star quarterback. Eventually he stopped wearing it as he settled into his new life as a college student. The jacket was first seen worn by Troy in the Season One episode "Pilot".
|In the study group's first year together at Greendale, Troy proudly wore his letterman jacket as a reminder of his glory days as the Homecoming King, superstar quarterback and all around BMOC at Riverside High. At the study group's first meeting, he is surprised when Annie recognizes him and she points that is he still wearing his letter jacket and is hurt he doesn't recognize her. After being mocked by both Annie and other Greendale classmates for living in the past, Troy asked Jeff's advice if he should stop wearing the jacket. Jeff tells him that it ultimately doesn't matter if he wears it or not; either decision wouldn't be based on what he wants to do but rather what the people around him want him to do ("Pilot").
|A few weeks later, Troy is wearing the letterman jacket in a crowded student lounge when he lets loose a girlish sneeze much to the amusement of the other students. Pierce then offers to help him improve his public image and immediately suggests he first get rid of his letterman jacket ("Introduction to Film"). Troy later wears the jacket to a date he has with female student named Randi. Annie had helped him plan the date which was at a nighttime outdoor concert being held on the campus quad. The date was going well and Troy was about to drape his letterman jacket over Randi when a jealous Annie interrupted them. She ruins the moment by taking back a family heirloom she lent him for the date, her grandmother's courting blanket, leaving a confused Troy and Randi behind("Home Economics").
|In Abed's fourth year at Greendale, he is anxious about the senior year as it might mean the end of the study group once they all graduate ("History 101"). Britta, who had been acting as his therapist at his insistence ("Introduction to Finality"), suggests that he go to a "happy place" inside his mind whenever he feels stressed out about the upcoming year. His "happy place" is revealed to be a sitcom version of his real life. Several flashes of this TV Show reality depicts how the study group looked like in their freshmen year. One of those sequences shows Troy in the study room wearing his letterman jacket. He is approached by who appears to be Evil Abed wielding a bone saw until it's revealed to be just Abed messing with him.
|Later near the end of the year, Abed studies the origins of the study group. While investigating their shared past histories, Troy is shown wearing the letterman jacket in a number of flashbacks to his time at Riverside High. One scene showed him wearing the jacket when Annie aproaches him and his entourage in the hopes of tutoring Troy for one of his classes. Another flashback has him wearing the jacket as he injured himself at party while doing a keg flip which cost him his scholarship. He was also wearing the jacket as he accepted awards at a high school honors ceremony. An "injured" Troy is later shown wearing the jacket when he and his friends go to the Greendale Mall. While they are eating frozen yogurt at Yogurtsburgh he receives a Greendale flyer from Ben Chang which inspires him to enroll at the school ("Heroic Origins").