Chris Taylor wants his old job back. The 42-year-old Tropical Smoothie Cafe franchise owner represented Virginia Beach's District 8 on city council from 2023 to 2024 before giving it up to run for mayor — a bid he lost — and now he's trying to unseat the man who took his place, incumbent Stacy Cummings, in the November 3 election.
The district itself is no small prize. According to planning department data cited by The Virginian-Pilot, District 8 has about 45,000 residents and more single-family homes than any of the city's other nine council districts. It stretches from Shore Drive to Virginia Beach Boulevard and takes in some of the city's wealthiest neighborhoods, making it one of six district seats on the ballot this year alongside Districts 2, 4, 6, 9 and 10, as The Virginian-Pilot reported separately.
A Seat That's Changed Hands Twice
Taylor first won the District 8 seat in 2022, the inaugural election under Virginia Beach's court-mandated 10 single-member district system, after being outraised in that race, per the newspaper's reporting. That system itself traces back to a 2021 federal court ruling in Holloway v. City of Virginia Beach, which found the city's old at-large council elections violated the Voting Rights Act by diluting minority voting power, according to The American Redistricting Project.
Taylor left the council in 2024 to run for mayor, finishing fourth in a five-candidate field as Bobby Dyer won reelection. That left the District 8 seat open, and Cummings won it in a four-candidate special election that November, taking roughly 50% of the vote, according to 13News Now. Taylor is now pursuing a master's degree in public administration at Regent University, where, notably, Dyer is one of his instructors.
Transparency Versus the Balance Sheet
Taylor's campaign centers on what he describes as taxpayers' entitlement to greater government transparency. He has said residents want a district council member who can explain city government to them, and he plans to require the city manager to update him on every economic development project so he can share that information with residents. He has pointed to Virginia Beach's 2024 nondisclosure agreement with Dragas Cos. over a proposal to redevelop the Virginia Beach National Golf Course, an agreement City Manager Patrick Duhaney executed that stirred citywide debate over transparency, as detailed by 13News Now.
The city says it used the nondisclosure agreement to protect confidential records, and former City Attorney Mark Stiles has said Virginia Beach provided Dragas leaders the same information available to any prospective golf-course buyer who asked. Dragas Cos. was one of nine proposals submitted to acquire the golf course. Cummings has pushed back on Taylor's framing, criticizing the challenger's claims about council corruption and backroom deals.
Cummings Leans on His Business Resume
Cummings, 68, is a retired car dealership owner who co-founded Priority Auto Group in 1998 and served as its vice president and CFO as the company grew to 19 dealerships before Lithia Motors acquired it, according to his campaign biography on his campaign website. He is a certified public accountant and a former U.S. Army military policeman. On council, he has said he helped trim the city budget last year and served as liaison to a process improvement committee.
If reelected, Cummings plans to continue pushing to reduce government spending and find tax breaks for residents. He has said he worked with fellow council members to advance District 8 projects and cites roughly $400 million in capital improvements flowing into the district, including Shore Drive upgrades, Great Neck Recreation Center renovations and sidewalks in Kings Grant. The Shore Drive Phase 3 project between Lesner Bridge and North Great Neck Road began construction in May 2025 as part of a three-year effort to improve pedestrian and traffic safety, according to We Love Shore Drive. Separately, the city's FY 2027-28 Capital Improvement Program sets aside $42 million for modernizing the Great Neck Recreation Center, funded through the Parks and Recreation Special Revenue Fund.
A Lopsided Money Race
Whatever momentum Taylor has built, he's running on fumes financially. Campaign finance records show Cummings had $113,701 cash on hand at the end of September, according to the Virginia Public Access Project, compared with just $7,484 for Taylor as of September 30. Cummings has drawn donations from prominent local figures including former Virginia Governor Bob McDonnell and former Virginia Beach Mayor Will Sessoms.
Taylor says he has support from residents looking to change city leadership and flip council seats. During his earlier term, he backed increased funding for arts and culture, enhanced youth sports programs and stormwater improvements affecting District 8 residents, and he has said he worked well with former council colleagues despite disagreements. Whether that record and his transparency message can overcome a steep fundraising gap will be decided when voters in District 8 head to the polls on November 3.
