First founded in 1933, Webb High School was from its establishment the first racially integrated high school in Shadowgard, though Arthur High School followed just a few years later, and what was then East Shadowgard High School (now North High) was integrated not long after the end of World War II. The school was the personal project of one Arnold N. Webb, at the time an unusually wealthy African-American scholar who appeared in Shadowgard seemingly out of nowhere, yet soon established himself as an eloquent speaker able to persuade a number of local citizens to aid in the completion of his plan. Though opposed in this effort by an affluent white citizens' group led by local agitator Erik Farbautisen, Webb managed to convince the actual residents of the crumbling Heights that this plan was in everyone's best interests, and ultimately prevailed. In the decades that followed, most to all of the remaining resistance in Shadowgard would crumble away, particularly as the other schools in town were integrated.

After a long period of stagnation following the death of Webb himself, the school has begun to flourish once again under the supervision of its new principal, Dr. Anne Webb, a descendant of Arnold who came on board in 2000 and whose apparent youth masks a genuinely intelligent and resourceful administrator. In the years since her arrival, Webb High School has begun to experiment with vocational training for those students who aren't college-bound, work study with local entrepreneurs such as club and entertainment magnate Jonathan Poe, smaller class sizes and new educational theories. The students and staff are also learning to take themselves less seriously, as Dr. Webb has quietly revitalized the school's prank wars, a tradition that dates back to its beginning - or, more accurately, she has made it implicitly clear that she's only too happy to look the other way as long as no one is hurt and school property doesn't come out too much the worse for wear because of it. Where speculation of Dr. Webb's own involvement in some of the staff-organized pranks is concerned, the principal remains conspicuously silent. The school is also regaining territory in athletics, where its Webb High Wolf Spiders share a fierce but friendly rivalry with the North High Vikings and Valkyries.