|“||What a year! Only two pregnancy scares!||„|
Leonard is an elderly business student at Greendale who has an antagonistic relationship with Jeff Winger, resulting in Jeff and other members of the Study Group to say "Shut up, Leonard..." followed by a comment (for example "Shut up, Leonard. No one knows what you're talking about."; "Shut up, Leonard. I talked to your son on Family Day. I know all about your gambling."). Though noticeably older than the other students at Greendale, he acts in as reckless and laid-back a fashion as many young adults, often using slang and engaging in such activities as playing pranks and bass guitar and encountering "pregnancy scares". He leads a rowdy, disobedient band of elderly Greendale students called the "Hipsters" (because they all apparently have hip replacements), which Pierce temporarily hang out in "Messianic Myths and Ancient Peoples." Among Leonard's various acts of rebellion are skinny dipping, the school party, vandalizing the walls with graffiti, and going on joy rides. Leonard changed his last name from to "Rodriguez" to win the Hispanic vote at the Greendale student elections.
Leonard claims to have been in the "Little Rascals", a popular show from the 1920s and 30s, indicating he is around 90 years old.
Leonard was introduced skinny dipping inside the pool located in Borchert Hall while an academic tribunal was convening over Britta having cheated on her Spanish test. Leonard took a billiards class along with Jeff and teased the ex-lawyer about the tight P.E. gym shorts he was forced to wear. Before April Fools Day, he interrupted Dean Pelton's daily announcement to yell "Baba Booey" into the P.A. microphone. That was shown to be a distraction so he could put a "Kick me" sign on the back of the Dean. He was also later seen with another elderly student graffitiing the administrations office desk. It was mentioned Leonard has at least one son, who informed Jeff of Leonard's gambling addiction during Family Day. On the last day of the 2009-2010 semester he was seen on the campus quad by Jeff doing Tai Chi. Abed shot a video year book which featured a clip of Leonard bragging that there had been only a few pregnancy scares this year.
Dean Pelton selected him to take part in the inaugural run of the Kentucky Fried Chicken Space Simulator. He was shown to be the leader of a rowdy, disobedient band of elderly Greendale students called the Hipsters whom Pierce briefly hung out with. On Valentines Day, Leonard went to Jeff's apartment and attended an impromptu party bringing a case of beer with him. Leonard later ran for student president and got into a spirited political debate with Magnitude (" Intro to Political Science"). He later participated in the 2010 Paintball Assassin serving as part of the security personnel of Fort Hawthorne. Once the school had been invaded by City College Storm Troopers, he joined up with the remaining Greendale students to form a rebel alliance. He sat in on a strategy meeting and hinted that he was once an actor on "The Little Rascal's". He was made a part of Jeff's paintball assault team who was tasked with taking out their Gatling gun implement. Leonard interrupted Jeff's inspirational speech by mentioning the fact that he was banned from a "Denny's".
Leonard participates in Dean Pelton's production of a new commercial for Greendale. Shirley mentions he has a YouTube channel dedicated solely to reviewing food. Leonard joined Abed in building Pillowtown fort and later assisted him as his top general in the Pillow and Blankets war with the rival Blanketsburg Fort. He is the one who suggests they unleash their WMD Pillow Man after the enemies in the blanket fort join forces with The Changlourious Basterds. In a Dreamatorium recreation by Abed of the events outside the Tranny Dance, it's revealed that Leonard was watching Jeff and Annie kiss while hiding in the bushes. When the study group instigates a riot in the cafeteria during a wake held for the recently departed Star-Burns, Leonard starts stealing from the salad bar. After the school comes under control of Ben Chang and his campus police force, The Changlourious Basterds, Leonard becomes the target of practical jokes from the head of security Joshua. A Youtube video is shown where he is reviewing Let's Potato Chips.
Leonard competes in the "Hunger Deans" tournament to determine who will get a spot in the highly coveted class "History of Ice Cream". He teams up with Annie Kim to try and eliminate Jeff from the competition. Later they pair up again for a Tango dance off. While the study group is distracted, he steals all the "registration balls" Jeff won for each of the study group members. He later helped throw a welcoming party for a potential new wealthy student named Archie DeCoste. Annie and Shirley learn that he is ahead of them in their competition for Valedictorian because in 1968 he earned an "A" in a class called "Rotary Dial Maintenance" and has been taking every class since then as Pass/Fail to keep a perfect grade average. When Dean Pelton confronts him about this, Leonard apparently quits school. However, because he scolded Leonard, the Dean is forced to grant him three wishes according to the Greendale by-laws. Leonard is later seen attending Jeff's graduation ceremony in the study room.
Leonard welcomes back Jeff with a raspberry when the lawyer makes an unexpected return to Greendale some time after his graduation. Leonard takes part in a rally led by Annie protesting the unfair grading practices of the Greendale teaching faculty ("Introduction to Teaching"). He also participates in the beta testing of a social media ranking app called "MeowMeowBeenz". Through the app he reaches level Three status and serves as member of the level Fives security force. Leonard has some advice to Abed when his fellow student has a meta crisis and subsequent breakdown in the schools hallway.
It is revealed that Leonard has been studying at Greendale since the 1970s when he finds a frisbee he had lost on the roof of the school in 1975. When prison inmates start attending classes using "telepresence robots", Leonard puts a "Parole Me" sign on the back of one of them, and later watches a fight between Jeff and an inmate. When all of the school's e-mails are leaked, Leonard says to Garrett he enjoyed his girlfriend "as much as she enjoyed his plagiarized poetry". Leonard plays "Dracula" in Abed's movie "Chief Starr and the Raiders of the Galaxy"; he kills Chief Starr as he tears up, in the middle of "a lunch order during an outtake".