Robert Fletcher Sr. is a product of the Washington Heights neighborhood on the Southside of Chicago. He attended Marcus Garvey School and grew up playing baseball since the age of five for Jackie Robinson West Little League where he was fortunate enough to make all-star teams every year. Fletcher attended Simeon Vocational School where he lead his Junior Varsity team to a City Championship in 1989 and was a starter on the 1990 Varsity City Championship Team. Robert was an All-City Baseball Selection in 1991 and 1992. He also excelled in the classroom as a member of the National Honors Society. He earned baseball scholarships from Michigan, Alabama State, Southern U, St. Joseph’s, and Grambling State University. Robert accepted the scholarship to Grambling and was a 3 year starter for the Tigers at second base and third base. He earned 1st Team All Southwest Athletic Conference(SWAC) and team MVP in 1995. He graduated in four years with a Bachelor’s Degree in Business Marketing in 1996 and was fortunate to become a member of Kappa Alpha PSI Fraternity, Inc. After college Fletcher had offers to play baseball professionally in the Independent League but declined them to get a job and take care of his son who was born my junior year at Grambling.
Fletcher was hired by Chicago Public Schools as a School Business Manager at Marcus Garvey School which he worked from 1996-2013. In 2013 he was promoted to the CPS School Support Center as a Senior Financial Specialist. Also in 1996 Head Coach Leroy Franklin at Simeon named Robert the Head Sophomore Coach of the baseball team. He went on to coach Simeon and win the 2000 City Championship and later on winning the 2012 Varsity Championship. He also volunteered coaching for Jackie Robinson Little League from 1997 to 2006. In 2007 he started working for the Chicago White Sox ACE Program as a coach and the Coordinator of College Placement. Since 1997 he has helped send over 300 young men to college on baseball scholarships and over 33 players drafted in the MLB Amateur Draft. In 2014 my God Son Ro Coleman won the College World Series while staring for Vanderbilt University. In 2016 his former player Corey Ray was drafted in the first round of the MLB Draft out of the University of Louisville. In 2020 another former player Ed Howard was drafted in the first round by the Chicago Cubs. Fletcher retired from CPS after 23 years of service and began working for Olive-Harvey College as the Director of Athletics in February of 2019.
Since being at the helm at Olive-Harvey College Athletic Department the Men’s Basketball team has won the City Colleges of Chicago Championship three consecutive years 2018-19, 2019-20, and 2021-22 seasons. 2018-2019 Men’s Basketball Player Kendrick Robinson earned NJCAA All-American Honors.
He later went back to Graduate School at Concordia University – Chicago and completed his Master’s Degree in School Leadership with a Type 75.
Fletcher has 4 children Robert II(27), Jeremiah(17), Faith(13), Joshua(11).