CHESAPEAKE, Va. (WAVY) — Bring along a pillow was good advice back in the late 1980s and early 90’s when Chesapeake City Council meetings would drag on well past midnight due to extended public comment periods. The always colorful T.J. ” Cowboy ” Carrawan, would rail against council members and administrators with his style of showmanship. It was an era where Chesapeake, with a population of about 152,000 saw explosive growth in residential and commercial development.

Carrawan, who ran and was defeated a dozen times in bids for city council, died in October 2014 at 71.

One can only imagine what “Cowboy” would say today about the state of politics in Chesapeake, which now has a population of 256,000.

This year, for the first time, elections for City Council and School Board are taking place during the closely watched congressional Midterm Elections. Half of the city will play a role in deciding who gets the second congressional seat currently held by Democrat Elaine Luria who is a former Naval officer. Challenger, Republican Jen Kiggins is also a former Naval officer. Recent polling from the University of Virginia calls this race a toss-up.

On the same ballot, residents in Chesapeake could really use a spreadsheet just to follow the 29 candidates and issues in City Council and School Board races.

With six of nine School Board seats up for grabs, no incumbents are seeking re-election and most of the candidates have never held public office.

With behavior that could get a child sent to the principal’s office, parents across the country have disrupted school board meetings in disputes over mandatory mask policies, the content of library books, and Critical Race Theory which does not exist in Virginia public schools but governor Glenn Youngkin banned it anyway.

In Chesapeake, several candidates have expressed concern about mental health care for students, parental involvement, and improvements to special education programs.

In the City Council elections, a republican divide has emerged in races that are -on paper- nonpartisan.

Current Councilwoman Susan Vitale and political newcomer Amanda Newins are the top fundraisers so far in this year’s race according to campaign finance reports compiled by the Virginia Public Access Project. Vitale has raised nearly $60,000 while Newins has collected roughly $50,000.

This is where things get messy.

Newins, who is an attorney, was recently accused of abuse of a family member in a civil lawsuit. Newins calls the allegations baseless.

Then, six elected leaders withdrew their support of Newins, although 10 On Your Side found no evidence they endorsed her.

The Republican Party of Chesapeake gave the nod to Newins instead of incumbent Vitale. Vitale, who was first elected in 2018, blames the endorsement loss on her decision to vote for former councilman Dwight Parker to fill an unexpired term on the city council instead of Tanya Gould.

Parker in the past aligned himself with the Democratic party, while Gould is a Republican.

The November 2022 turnout numbers will be closely scrutinized in the largest city in the state with an at-large voting system. In May 2020, more than 99,000 people voted in the School Board election while close to 90,000 people voted in the City Council election.

Chesapeake Council meetings are televised live on social media and they end at a reasonable hour. Had T.J. “Cowboy” Carrawan crossed paths with today’s technology his presentations to City Council would have had the potential to go viral.