About 1860 an Oregon pioneer, Clinton Kelly (1808-1875), donated two acres of land to what soon became Multnomah County School District No. 2 with the stipulation that the property would always be used for education purposes or else it would revert back to his family or descendents. That land today lies between Southeast 26th and 28th Avenues, Powell Boulevard and Franklin Street. Clinton Kelly School, which was made of logs, had already been built on the property. The log structure was replaced by a simple wooden building, which was torn down in 1893 when a more substantial elementary school was built. This was done soon after School District No. 2 was annexed to Portland Public Schools.
The school was enlarged in 1910 and 1912. By 1929 the elementary students had been displaced and moved to Daniel A. Grout School on Southeast 31st Avenue and Holgate Boulevard. The empty school building then became the temporary home of the High School of Commerce, a school that had originally been located on what is now the PSU campus. The High School of Commerce was an independent high school with a focus on business. Created in 1916 as Commercial High School, its name was changed in 1917 to the High School of Commerce. In 1929, this school moved across the river to the current Cleveland High School site. In a dramatic show of transition, the High School of Commerce students marched from the old site downtown over the Ross Island Bridge, up Powell Boulevard, and into the new location. The school’s name lengthened to Clinton Kelly High School of Commerce, and in 1929 the cornerstone was laid for a new, much larger building and the former elementary school was torn down.
The high school, designated as a school for students pursuing business education, gradually added courses until it became a comprehensive high school in 1948. Again the name was changed, this time following the practice in Portland of naming high schools after United States presidents. Named for the 22nd and 24th president of the United States, it became Grover Cleveland High School. Its symbol, which had been the STENOS (short for “stenographers”) became the INDIANS. (At that time the Portland baseball team, the Beavers, had the Ohio baseball club as its parent organization.) The school’s newspaper, which had been THE BLOTTER, became THE TOMAHAWK and the yearbook went from THE LEDGER to THE LEGEND.
In the late 1950’s the building was enlarged to include the East Wing and the new gym. The site of the old gym is now the CHS library. During the 1976-1977 school year the Cleveland Mall was opened in the cafeteria, as Cleveland High School became a business magnet for Portland Public Schools, thus honoring its “Commerce” roots. In 1988 another change took place: the symbol was changed from the INDIANS to the WARRIORS, and the name of the school newspaper went from the THE TOMAHAWK to the THE CLARION. In 1989, Cleveland High School became the new home of Portland Public Schools’ only theater organ, the Kimball Pipe Organ, which had been housed at Benson High School. The organ underwent a two-year restoration, and organ concerts began in the spring of 1991. Other additions over the years included a remodeled science facility, the Student Services Center, the Cleveland stadium, and the School Based Health Center.
Throughout all the name changes, different buildings and other additions, Cleveland High School has remained one high school in spirit with a long and happy tradition.