Doubtlessly named after Grover Cleveland (1837-1908), who’s remembered for serving two separate terms as U.S. President. It was definitely named by 1891, during the four-year lull between Cleveland’s terms, but I suspect it was actually named in November 1888 – shortly before Cleveland lost his re-election bid to Benjamin Harrison – on the same tract where nearby Murchison Avenue was born. The latter street’s name is a reference to the “Murchison Letter”, the political stunt hatched by Pomona Republicans that led to Cleveland’s defeat. (See that street’s entry for the story.) Those same Pomona Republicans would have named Cleveland Street ironically, since Grover Cleveland was a Democrat. The San Bernardino Freeway fittingly cut Cleveland Street in two in the 1960s.