Old Forester was named for Dr. William Forrester, a Civil War hero and one of the investors who backed George Garvin Brown’s groundbreaking idea to sell bourbon only in bottles to ensure quality and consistency. Dr. Forrester himself was not old; he was just 34 when the brand was founded in 1870. The “Old” in the name referred to the fact that the bourbon was matured in barrels.
Did you notice the discrepancy in the names? The bourbon was originally called Old Forrester, with three Rs, until 1890, when Dr. Forrester retired and the spelling was changed, says Brown-Forman master distiller Chris Morris.
Source: Woodford Reserve Bourbon Academy