Though he twice hit more than 20 home runs in a season with the Reds, his best statistical year came in 1989 as a member of the Boston Red Sox to whom he was traded along with relief pitcher Rob Murphy for switch-hitting first baseman/outfielder Todd Benzinger and pitcher Jeff Sellers. During that season, he hit .277 with 30 home runs and 108 runs batted in. That offseason, as a free agent, Esasky signed a three-year, $5.6 million contract with the Atlanta Braves, but was forced to retire after playing just nine games due to developing vertigo stemming from an ear infection. His salary was paid for by insurance.
As of 2021, Esasky is running a health and wellness center near his hometown of Hialeah, Florida.

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