In the early 1920s, there was a growing need for the students graduating from the Jefferson and Vista Grande elementary schools to pursue their higher education in the community.
Daly City was well-established, but there was a vast unincorporated area called "Colma” to the south and west of these elementary schools. To attain a high-school education, the students had to ride the #40 Trolley Line to South San Francisco Baden School or find a high school in San Francisco to take them. Either way, it was discouraging and difficult to continue their education.
To correct this void, the Jefferson High School District was formed in 1922. The boundaries of the school district included land from the Bay (Brisbane/Bayshore City) to the ocean (named "Colma” west of San Bruno Mountain), south from the San Francisco city limits to the area west of San Bruno and into Pacifica. This territory was sparsely populated with hog farmers and vegetable and flower growers. A bond issue for $180,000 to build a modern school was passed before a site was chosen. Nevertheless a student body of 50 students and three teachers began classes in the old Jefferson Hall in Colma. The school board consisting of five trustees was thrust into a community fracas immediately on the decision of a site for the new school. The two developing communities, Vista Grande and unincorporated "Colma”, took sides in a heated public disagreement as to where to best place the new high school, opinion differing as to future directions the shifting population would take — north, east, or west of the elementary schools — and the distance their kids would have to go to get to the school.
Edgewood Terrace to the north of "Colma” near Hillside Boulevard was one choice. Another popular choice was to use the spacious 20-acre grounds of the Union Coursing Park that fronted the Mission Road. On the grounds, near the Southern Pacific railroad tracks, stood a race track where greyhound dogs had chased rabbits for sport for many years. In an election on March 29, 1923, the Union Coursing Park was chosen as the site of the new school. Neil O. Best was chosen as chief administrator and the construction of Jefferson High School began. Unfortunately, the money allocated for the project ran out, and a building tax had to be levied to complete the structure. The population continued to grow rapidly, and the school was enlarged n 1925, 1928, 1936 and 1947 until the school covered most of the original Coursing Park with 27 classrooms, industrial classes (metal, wood, auto), a gymnasium, a swimming pool and a little theater. Industrial art classes were very popular in this farming community at that time. In addition, the dedicated faculty presented the most modern and complete course of study found anywhere. By 1939, the enrollment had increased to more than 700, with a faculty of 28.
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The swimming pool had been dedicated June 5, 1938, and with this modern pool Jefferson High boasted one of the finest athletic plants in the entire Bay Area. In 1947, Mike Orlich became a teacher at Jefferson High School. Orlich coached, refereed, administered and helped to promote athletics in the northern half of San Mateo County. He coached basketball and track and field, and was the school’s athletic director. One of Orlich’s star students was John Madden. Madden excelled in basketball, baseball and football. After graduation from college, he was drafted into the NFL by the Philadelphia Eagles. In 1967 Madden became head coach for the Oakland Raiders. In the 10 years he was coach, his team was in the playoffs eight times and he won Super Bowl XI in Pasadena. Madden later became a well-respected sports announcer, a position from which he recently retired.
After World War II, Daly City began experiencing growing pains and there was a push to incorporate the land west of Junipero Serra into Daly City. The Broadmoor area and land along 87th Street had been attracting home construction. In 1947, Henry Doelger acquired vast tracts of land and began construction of the Westlake homes that were to eventually number in the thousands. With all of this development, thousands of youngsters needed schooling, and the single high school — Jefferson — was not large enough to satisfy the demand.
By the early 1960s, the Jefferson High School plant began showing signs of deterioration, and new classrooms and buildings were planned. By 1963, the "old” Jefferson High School was replaced by new buildings and eventually became the "newest” school in a school district that was expanding rapidly and now included a string of five high schools (the "new” Jefferson, Westmoor, Serramonte, Oceana and Terra Nova) extending to the borders of Pacifica. The students of Serramonte eventually were absorbed into other schools, and that site houses district offices.

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