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After graduating from college, Levine worked in the Merchandising Department at Family Dollar, rising to the position of Senior Vice President-Merchandising and Advertising from 1981 to 1987. Thereafter, he served as President of Best Price Clothing Stores, Inc. from 1988 to 1992.
From 1992 to 1996, Levine was self-employed as an investment manager.
In 1996, Levine rejoined Family Dollar and served in various positions until he became Chief Executive Officer in August 1998.
In July 2014, Levine oversaw the buyout of Family Dollar by Dollar Tree in a deal totaling $8.5 billion. Levine will remain with the company following the merger and be appointed to Dollar Tree's board of directors.
While CEO of Family Dollar in 2009, Howard R. Levine earned a total compensation of $5,612,726, which included a base salary of $948,654, a cash bonus of $1,894,615, stocks granted of $1,338,224, and options granted of $1,308,528.