White became involved with the East of the River Clergy Police Community Partnership (ERCPCP) while in high school. He remained involved as a mentor and sports coach while in college, and joined ERCPCP as a paid community outreach worker about 2006. Interviewed by The Washington Post in January 2008, White said that a large number of his friends were robbed in D.C. in 2007, and he knew five people who had been murdered that year. "Living in the streets, you get numb to it and learn to cope with it. It's hard for me to cry when I go to funerals anymore," he said. White, who lived in the Washington Highlands neighborhood, denounced the 2007 shooting of 14-year-old DeOnte Rawlings by an off-duty D.C. police officer as "injustice."

In November 2007, White founded Helping Inner City Kids Succeed (HICKS), a nonprofit organization dedicated to helping poverty-stricken children east of the Anacostia River in Washington, D.C. White received the Linowes Leadership Award from the Community Foundation for the National Capital Region in May 2008 for his work with at-risk young people. In 2011, an editorial in The Washington Post said White's nonprofit "is doing interesting work with inner-city youth" and that White had real insight "into the problems confronted by students in Ward 8 schools".

During his time as a community activist, White was mentored by William O. Lockridge, a longstanding member of the D.C. Board of Education. He also became known as a protégé of Marion Barry, the D.C. Councilmember representing Ward 8 and former Mayor of the District of Columbia.

Following Lockridge's death, White ran to fill Lockridge's unexpired term on the Board of Education, and was endorsed by both Barry and Lockridge's widow. White won the April 26, 2011 special election with 32.8% of the vote in a crowded field, defeating second-place candidate Philip Pannell by 6%. White ran for reelection in November 2012, with Pannell his sole opponent. White won the election with 73.3% of the vote to Pannell's 26.3%, a margin of over 13,500 votes.

White helped break ground on a new Ballou High School building in March 2013. He praised charter schools for improving education, but criticized Kaya Henderson, Chancellor of the District of Columbia Public Schools, for failing to come up with a plan to improve education for children in traditional public school settings.

The Board of Education position paid a stipend (not a salary) of $15,000 a year. In late February 2014, White took a job as a supervisor in the "Roving Leaders" at-risk youth program in the District of Columbia Department of Parks and Recreation. However, city law prohibited Board of Education members from holding city employment, and White resigned his position on the Board on March 5, 2014.

In April 2014, eight-year-old Relisha Rudd disappeared while her family was staying in a city-run homeless shelter. The child's disappearance created a citywide outpouring of concern. White, who had met the girl, worked with several community groups to organize three canvases of the area to find the girl (or her body). (The girl remained missing as of April 2016.)

On Sunday, November 23, 2014, 78-year-old Marion Barry died at United Medical Center, hours after having been released from Howard University Hospital. White was one of the people Barry called immediately after leaving Howard. On December 16, The Washington Post reported that White was one of many individuals contemplating a run for Barry's Ward 8 council seat. White was one of the first to file as a candidate in the special election to fill the remainder of Barry's term (which expired on December 31, 2016), doing so in late December 2014. Under District of Columbia Board of Elections rules that permit candidates to run under whatever name they wish, White asked for his name on the ballot to be listed as "Trayon 'WardEight' White". White later explained that friends began calling him by the nickname "WardEight" on Facebook, and he intended to use it on the ballot.

By the end of January 2015, White had raised a $2,562 in campaign donations. In comparison, LaRuby May had raised $177,405, and former Vincent C. Gray mayoral aide Sheila Bunn had raised $51,692. Despite the low level of initial fundraising, the Washington City Paper, quoting unnamed Ward 8 political insiders, said White probably shared the lead in the race with May. By the end of February, White had raised over $10,000 and had $12,000 in his campaign coffers.

On April 3, May easily won a Ward 8 Democratic party straw poll, confirming her lead in the Ward 8 race. May received 177 votes, followed by Trayon White with 79 votes, Natalie Williams with 77 votes, Sheila Bunn with 53 votes, and Eugene Kinlow with 30 votes. (All others received fewer than 30 votes.) Will Sommer, the writer of the influential "Loose Lips" political column for the Washington City Paper, observed that May's win may have indicated trouble for her campaign: May paid for a free barbecue for all comers just two blocks from where the straw vote was held, and Mayor Muriel Bowser stood on a nearby street waving a May campaign sign. However, May mustered fewer than 200 votes. Candidates Stuart Anderson and Jauhar Abraham dropped out of the race over the next four days, and urged voters to support Trayon White.
Turnout in the Ward 8 special election on April 28, 2015, was especially high, with more than 6,200 ballots cast by the ward's nearly 52,000 voters. That was nearly 75 percent of the turnout in the 2014 mayoral primary—far exceeding expectations. Preliminary election results released late in the evening on April 28 showed LaRuby May with 1,711 votes and Trayon White with 1,559 votes, a difference of just 152 ballots. Although May outspent White 16-to-1, election observers said White had surged late in the race as an "anti-establishment vote" and that he had consolidated much of his support by drawing it from other candidates in the crowded field. Will Sommer, writing in the Washington City Paper, argued that White lost the race because Marion Christopher Barry, son of the former mayor, had stayed in the race despite a floundering campaign and his candidacy had diverted votes from White.

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