Over the years Stamford High School has had its fair share of famous alumni. From artists to athletes, here are  five notable alumni of the “School on the Hill.”

1. Tony DiPreta

Anthony “Tony” Louis DiPreta was a comic book and comic strip artist. He graduated early from SHS in 1943 to join the war effort. His most famous comic strips were, “Joe Palooka” and “Rex Morgan, M.D.” DiPreta took art classes at SHS which sparked his interest in drawing comics. He went on to study at the University of Connecticut and Columbia University. In 1941, DiPreta had his first solo comic publish in “National Comics.” During this time World War II was taking place. DiPreta was rejected for WWII service because of his health conditions. He went on to draw for many well known comic strips and also completed five life size mosaics depicting patron saints. After retirement, DiPreta enjoyed going to Hawaii with his wife during the winter and painting the beautiful scenery. He died June 2, 2010 at age 88.

2. J. Walter Kennedy

James Walter Kennedy served as Stamford’s mayor for two terms long after graduating from SHS in 1930. His first plan was urban renewal in Stamford. From 1963 to 1975, he served as the commissioner of the National Basketball Association. During his time as commissioner, the league size doubled and the number of fans attending games tripled. Kennedy was able to bring the league back to financial stability. Kennedy also started his own public relations business. One of his clients was the Harlem Globetrotters. While traveling with the team he visited 52 countries and had the opportunity to meet three popes. Kennedy also served as a chairman for the International Special Olympics. He was rewarded for his efforts to promote racial harmony in Stamford. Kennedy died June 26, 1977 at age 65.

3. Vladimir Ducasse

Vladimir Ducasse is a Haitian born professional football player that graduated from SHS in 2006. He played for the New York Jets and Minnesota Vikings. Ducasse currently plays for the Chicago Bears. During his time at SHS Ducasse was named First Team All-State and First Team All-FCIAC. He went on to attend the University of Massachusetts-Amherst. Ducasse was drafted in the 2010 NFL Draft by the New York Jets in the second round as the 61st overall pick and was considered one of the top offensive guard prospects in the draft. He was signed to the Jets on a 3.25 million four year deal, playing two games in his rookie year. He now plays with the Chicago Bears after signing a one year contract on March 16, 2015.

4. Stephanie Izard

Stephanie Izard is an American chef who graduated from the Stamford High Class of 1994. She was the first female to win Bravo’s Top Chef in the fourth season of the show. Izard won the $100,000 prize which helped kickstart her career as a chef and restaurant owner. She opened her first restaurant in 2004 called Scylla. In 2007 she closed this restaurant and now co-owns two Chicago restaurants, Girl and the Goat and Little Goat. Izard is opening a third restaurant in 2016. Izard has appeared on Top Chef many times after her win both as a chef and as a judge. She attended the University of Michigan and the Le Cordon Bleu College of Culinary Arts Scottsdale. Izard currently resides in Chicago where she manages her three restaurants.

5. Chordale Booker

Chordale Booker is a boxer and recent Stamford High Alum from the class of 2009. With hard work and persistence after getting second place in the Nationals in 2014, Booker was able to achieve his ultimate goal of winning the USA Boxing National Championship in 2015. At SHS Booker had a hard time, he was not the greatest student and had family troubles because his dad was in and out of jail through his childhood. After he graduated he was able to start boxing at a local gym. He realized that boxing was something he could do to get off the streets and succeed. Today Chordale Booker is fighting in the 165 pound weight class and is training in hopes of making the Olympic Team.