Leonard "Lenny" Erving Easterly

LEONARD (“LENNY”) ERVING EASTERLY, SR., was born in Fort Wayne, Indiana, on October 11, 1945, to William Easterly III and Rosemary Easterly, who both preceded him in death. After graduating from Harmar Elementary School, Leonard attended Central High School, where he participated in a variety of extracurricular activities, including track, Dramatics, Phy-Chem, and Boosters. Still, he was most known for being the Central Tiger mascot (he wore the tiger suit at athletic events) and serving as his senior class president. His class also voted him “Best Citizen” in 1964.

Soon after high school, Leonard married Christine Outlaw, which resulted in two children.

Eager to establish himself professionally, in the 1970's, Leonard joined his father in Chicago, Illinois, where he accepted a position as a tax preparer at H&R Block and took college courses at Roosevelt University. His ability to quickly learn the business was instrumental in his quick promotion to an office manager position, which laid the foundation for his future tax business. In 1973, he became a life insurance salesman for Supreme Life Insurance Company.  The April 18, 1974 issue of Jet Magazine recognized him as a “Supreme Men of the Month” for his dedicated service and sales ability. He spent the rest of the decade working for a series of insurance companies, including Mutual Trust Life Insurance Company, through Sanmar Financial Planning Corporation, and Mutual of New York (MONY) through an agency out of Hinsdale, Illinois. His outstanding sales achievements continue to earn him widespread recognition and notable awards. In 1977, Leonard’s receipt of the 1977 Mutual Trust Life Achievement Award, the highest honor given by the company to one of its representatives, was featured in the April 1978 issue of Ebony Magazine. He was a member of the Million Dollar Round Table, a global, independent trade association of the world’s leading life insurance and financial services professionals. He was awarded an all-expense-paid trip to San Francisco as the Mutual of New York Man of the Year for outstanding sales. His business know-how and savvy earned him national and international vacations  to Puerto Rico, New York City, NY, Scottsdale, AZ, Nassau, Bahamas, Ocho Rios, Jamaica, Miami, FL, Reno, NV, and New Orleans, LA.

In 1972, Leonard married Liethia Mitchell. Their 33-year union resulted in two children.

Leonard solidified himself as a business professional in the early 1980's by starting his financial planning, tax preparation, and insurance sales and investment businesses – Easterly Associates and Plaza Insurance Agency, Inc. – in Evergreen Park, Illinois.

Over the next several decades, Leonard made Chicago’s South Loop area the home of his tax preparation and expanding business interests.  While the primary purpose of Main Street Communications was to sell and repair pagers and cell phones and provide food service out of Mr. Leonard’s Soul Food & Deli, he remained dedicated to providing tax preparation services through both establishments. In 2015, Leonard closed his last office, Tax Service Center, but continued to prepare tax returns until his declining health no longer allowed.

In his leisure, Leonard enjoyed listening to old school R&B soul music, fine dining, and watching sports and the “Price is Right.” Still, as his longtime business supporter and trusted friend, Charmaine Cooper, and others can attest, what he enjoyed most in life was his work. While many will remember him for his generosity, we will never forget the nonconformist who, as Frank Sinatra sings, lived his life “his way.”

Leonard leaves behind four children – Leonard Easterly, Jr., Anthony (Libby) Easterly, Sr., Jason (Kelli) Easterly, and Bianca (Tony) Easterly Cattelan; thirteen grandchildren – Candice Dennis, Anthony Easterly, Jr., Jazmine Edwards, Imari Edwards, Leonard Easterly III, Aysia Easterly, Gabrielle Easterly, Kendall Easterly, Isiah Easterly, Sophia Easterly, Phoebe Easterly, Maxwell Cattelan, and Dominic Cattelan; siblings – William “Bill” Easterly IV (deceased), Donna Jean (William) Scott, Joyce Brooks (deceased), Yvonne Easterly, Jennifer (Lee) Curry, Mitchell Easterly, Frank Nelson, Jeneer Easterly-Majors, Obie Nelson, Vanessa Easterly Nelson, and Demetrius (Stephan) Taylor Green; and a host of other family members, friends, caretakers, and lifelong clients.

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