|“||Hey guys, thanks for eating all the macaroni!||”|
–Leonard, "Romantic Expressionism"
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 ("Advanced Criminal Law"). Leonard took a billiards class along with Jeff and teased the ex-laywer about the tight P.E. gym shorts he was forced to wear ("Physical Education"). Before April Fools Day, he interrupted Dean Pelton's daily announcement to yell "Baba Booey" into the P.A. microphone ("The Science of Illusion"). 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 ("Basic Genealogy"). 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 ("Pascal's Triangle Revisited").
|“||Where are the white women at?||”|
–Leonard, "Early 21st Century Romanticism"
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".
|“||There are those who thought that midnight might come and go and nothing would happen. Well I was in Korea and I knew the sound of crap when it was about to hit the fan.||”|
–Leonard, "Pillows and Blankets"
Leonard participates in Dean Peltons 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 layer 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.
|“||I knew this day would come. I'm out of here.||”|
–Leonard, "Basic Human Anatomy"
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. He was revealed to be on track for Valedictorian in competition with with Annie and Shirley. It was shown that due to his getting an "A" in a class called "Rotary Dial Maintenance" back on 1968, he's been taking every class since then as Pass/Fail to keep a perfect grade average. When confronted by Dean Pelton about this, Leonard apparently quits school. However, because Dean Pelton scolded him, be is forced to grant Leonard three wishes according to the Greendale by-laws. Leonard is later seen attending Jeff's graduation ceremony in the study room.
Leonard is part of one of the best-known running gags on the show. His rude remarks typically elicit a response of "Shut up, Leonard" from Jeff or others.
|“||You're gonna look like an ass in those.||”|
|“||Shut up, Leonard! I talked to your son on Family Day. I know all about your gambling.||”|
–Jeff, Physical Education
- Leonard fought in the Korean War on the North Korean side. Or so he claims.
- He has a son from whom he stole pillows and blankets for Abed and Troy's blanket fort ("Conspiracy Theories and Interior Design").
- He has a daughter who gave him a Blu-ray player.
- His frequent delinquency has caused him to be ignored by his children.
- He has several popular YouTube channels which he uses to review food and clothing.