Thinking about running for office?  Here is a list of upcoming elections and what seats will be available that represent Chesapeake, Virginia… including Mayor of Chesapeake, which will be back on the ballot in May of 2020.

How Much Do Our Elected Officials Get Paid?

In Virginia, our state and local elected officials are paid very modestly as our state senators salaries are $18,000 and House of Delegates Representatives are paid $17,640 per year. The highest paid state legislators are those in California, which make $104,118 to serve their citizens.  Chesapeake City Council recently voted themselves their first raise in 22 years, which will become effective on July 1, 2018. City Council Members will now be paid $25,000 annually and the Mayor of Chesapeake will be paid $27,000 annually. Chesapeake School Board members are paid $12,000 annually.

There is BIG MONEY however in the five constitutional officers that Chesapeake citizens elect including Clerk of Court, Treasurer, Commonwealth Attorney, Sheriff, and Commissioner of Revenue.  The Clerk of Court will be up for re-election in November of 2019 and the rest of the positions will be up for re-election in 2021.  The majority of these roles recently ran unopposed and all pay over a six figure salary!

It is always interesting to look at how much money these candidates fund raise for their campaigns via the non-profit Virginia Public Access Project website  The Associated Press and in turn The Virginian Pilot were quoted as saying “Behavior that would get lawmakers locked up in other states or at the federal level is perfectly fine in the Old Dominion. Virginia is the only state where lawmakers can raise unlimited campaign donations from anyone, including corporations and unions, and spend the money on themselves.”

The Virginian Pilot article goes on to specifically mention “Chesapeake Democrat Del. Lionell Spruill, who hasn’t faced an opponent in two decades. Since 2011, Spruill has spent $300,000 from his campaign account on numerous luxuries: a membership in a private business club, meals at Ruth’s Chris steakhouses around the country, and more than $2,000 at high-end Richmond restaurants during legislative sessions. More than 90 percent of the money Spruill raised came from corporations, trade organizations or special interest groups.”

Ironically some of the highest paid constitutional positions in Chesapeake have the lowest campaign costs.


Running a solid campaign requires proper planning.  If you intend on running under either the Democratic or Republican party, you generally need to first seek approval and then participate in a primary election. This typically requires paperwork to be filed by March for a June primary race and November election. However if you are filing as an Independent candidate, then there is generally a cut off date towards mid June to file your candidacy paperwork for a November election.

However if you are running for a local election in Chesapeake, which are currently held in May, the dates are earlier. You would need to file your paperwork in December if associated with a political party for a possible primary in March and then voting in May.  If you were an Independent candidate, then your paperwork would typically need to be file by March.

For local Chesapeake elections, you need to collect the signatures of 125 registered Chesapeake voters. For the Virginia House of Delegates you also need 125 signatures from registered voters and for Virginia State Senator you need 250 signatures from registered voters. The signatures need to be notarized and need to be collected during certain time window dependent upon the election date.

Specific details and forms can be found at the Virginia State Board of Elections website and at the Chesapeake Registrar’s Office for local elections.

Clerk of the Court – November 5, 2019 

Former Chesapeake Mayor, Dr. Alan Krasnoff edged out Democratic candidate Kevin O’Brien for the vacancy in this role in the November 7, 2017 election. This was a special election with a shortened term intended to finish the original term of the late Faye Mitchelle. This position will be back up for election on November 5, 2019.

The approximately salary for Chesapeake Clerk of Court is $154,000. Visit the Clerk of Court page on the Chesapeake city website for a description of responsibilities.

Virginia General Assembly – Odd Numbered Years

News Update: Federal court rules against Virginia House of Delegates in racial gerrymandering case, and new districts are set to be drawn by October 30, 2018.

In case it has been a while since you studied this in school or helped your teenager with their homework, here is a quick reminder and a few links on how the Virginia General Assembly in Richmond works. The General Assembly consists of 140 elected representatives and two houses.  The upper house is the Senate of Virginia and consists of 40 Senators who are elected to serve four year terms. The House of Delegates is considered the lower house and has 100 elected representatives that serve two year terms.

Virginia State Elections are on Odd Numbered Years

Within Chesapeake, we have three different senate districts, and five different House of Delegates districts.  At the state level, you are required to live in the district that you want to represent. All three senate seats (4 year terms) and all five House of Delegates seats (2 year terms) will be part of the the November 5, 2019 election.

Find your legislators by typing your address into to

Virginia General Assembly Website:

Virginia State Senate District 14 – November 5, 2019 

District 14 includes parts of Chesapeake, Virginia Beach, Isle of Wight County, Southampton County, Franklin City, Portsmouth, and Suffolk.

Current Senator in District 14

Republican Senator John A. Cosgrove Jr.

First elected August 6, 2013 in Special Election

VPAP for Senator John Cosgrove

Virginia State Senate District 05 – November 5, 2019 

District 5 includes parts of Chesapeake and parts of Norfolk.

Current Senator in District 05

According to Ballotpedia, “a special election for the position of Virginia State Senate District 5 was called for November 8, 2016. The seat was vacant following Kenny Alexander’s (D) election to the office of Norfolk mayor. Del. Lionell Spruill (D) was unopposed in the special election. In turn, Lionell Spruill’s House of Delegates seat went to Cliff Hayes.”

VPAP for Lionell Spurill Sr.

Virginia State Senate District 18 – November 5, 2019 

District 18 is the smallest district within Chesapeake encompassing Taylor Road and Pughsville areas of Chesapeake.

However overall it is quite large as it also includes parts of Brunswick County, Franklin City, Isle of Wight County, Portsmouth City, Southampton County, Suffolk City, Surry Count and all of Emporia City, Greensville County, & Sussex County.

Current District 18 Senator

Democratic Senator L. Louise Lucas 

Senator L. Louise Lucas was first elected to the chamber in 1991.

VPAP for L. Louise Lucas

Virginia House of Delegates (2 Year Terms) – November 5, 2019

News Update: Federal court rules against Virginia House of Delegates in racial gerrymandering case, and new districts are set to be drawn by October 30, 2018.

21st District (Map of Part of Chesapeake and Virginia Beach)

Delegate Kelly K. Convirs-Fowler is a Democratic who narrowly beat Ron Villanueva in the 2017 election.

VPAP for Kelly Convirs-Fowler


76th District (Map of Part of Chesapeake and Part of Suffolk)

Delegate S. Chris Jones has served since 1998. He is Republican and ran unopposed in the last election.


VPAP for Chris Jones


77th District (Map of Part of Chesapeake and Part of Suffolk)

News Update: 77th District is part of the federal court racial gerrymandering ruling and is scheduled to be redrawn.

Delegate C. E. “Cliff” Hayes, Jr. 

special election for the position of Virginia House of Delegates District 77 was called for November 8. The seat was vacant following Lionell Spruill‘s expected resignation in November 2016. Cliff Hayes was unopposed in the special election.  He then defeated Green Party candidate Jeff Staples in the 2017 election. Cliff Hayes was previously a Republican member when he served on Chesapeake city council. He is currently a Democrat.

Cliff Hayes Becomes A Democrat on June 24, 2007- The Virginian Pilot 


78th District (Map Part of Chesapeake and Part of Suffolk)

Delegate James A. “Jay” Leftwich Jr.

Delegate Jay Leftwich Jr is a Republican was elected in 2014 and ran unopposed in the 2017 election.


VPAP for Jay Leftwich Jr.


81st District (Map of Part of Chesapeake and Part of Virginia Beach)

Delegate Barry D. Knight

Delegate Barry Knight is a Republican that has served since 2009. Democratic candidate Kimberly Tucker ran against him in the 2017 election.


VPAP for Barry Knight


Mayor of Chesapeake – May 2020

Mayor Richard W. “Rick” West

VPAP for Rick West 


Three Chesapeake City Council Seats – May 2020

Robert C. Ike, Jr. 

VPAP for Robert Ike, Jr.

S. Z. “Debbie” Ritter

VPAP for Debbie Ritter

Dwight Parker

VPAP for Dwight Parker

Four Chesapeake School Board Positions – May 2020

Full bios of the school board members can be read on the Chesapeake Public School website.

Mr. C. Jeff Bunn – Republican – Chairman of the School Board. He was first appointed to the school board in 2006 and then elected in 2008. He was re-elected in 2012 and 2016.  He was appointed Vice Chairman of the School Board in 2014 and became Chairman in 2016. Mr. Bunn is employed by the Chesapeake Parks, Recreation, and Tourism Department as a sales manager in the tourism division.

VPAP for Jeff Bunn

Mrs. Victoria L. Proffitt –
Republican – is the Vice Chairman of the Chesapeake School Board.  According to the Chesapeake Public Schools website,  “Victoria L. Proffitt was elected to the School Board in 2012 and re-elected in 2016. She was elected as the School Board Vice Chairman in 2016 and 2017.”  She is the Treasurer for the Chesapeake GOP and her son Nicholas is the Chairman of the local Republican party.

VPAP for Victoria Proffitt


Mr. Samuel L. Boone, Jr. was elected to the Chesapeake School Board in May of 2012 and re-elected in 2016. No noted VPAP for Samuel Boone.


Mr. Thomas L. Mercer, Sr. has been on the School Board since 1996.

VPAP does not show incoming campaign donations for Thomas Mercer, but rather lists him a contributor.


November 2020

The next Presidential election will be in November 2020. Our local ballot will also include the U.S. Senator seat currently filled by Senator Mark Warner (D) along with the two US House of Representatives that represent Chesapeake, VA.

Virginia Federal Elections on Even Numbered Years

US Senator – November 2020 (6 Year Term)

US Congress members of the House of Representatives serve two-year terms and are considered for reelection every even year. Senators however, serve six-year terms and elections to the Senate are staggered over even years so that only about 1/3 of the Senate is up for reelection during any election.  Our two Senators have elections in November 2018 and then November 2020.

US House of Representatives – November 2020 (2 Year Term)

The two seats of District 3 & 4 of the US House of Representatives that serve Chesapeake, Virginia will be on the ballot in November 2020 along with the Presidential election.

Highly Paid Constitutional Officers in Chesapeake Elected by Citizens

All of these highly paid Chesapeake constitutional offices had no competition on the November 2017 ballot.  Several of these positions raised minimal if any funds for their campaigns.

Commonwealth Attorney – November 2021 

Nancy Parr is a Republican that was elected in 2006 as the city’s Commonwealth Attorney. She faced no competitor in November 2017.

Salary approximately $174,200 according to data from 2015.

Job Description of Commonwealth Attorney

VPAP for Nancy Parr


Sheriff – 4 Year Term – November 2021

Jim O’Sullivan is a Republican ran for office against Les Smith in November 2013 and won. He faced no competitor in November 2017.

Approximately salary $147,000 according to data from 2015.

Sheriff Job Description

VPAP for Jim O’Sullivan


Chesapeake Commissioner of Revenue – 4 Year Term – November 2021

Francis Xavier King edged out Christie New Craig in the Republican primary race. He was the only name on the general election in November 2017.

Approximate salary $136,000 according to data from 2015.

The Office of the Commissioner of the Revenue assesses individual and business personal property taxes, prorates personal property taxes on motor vehicles and trailers, issues City business licenses, administers special taxes on meal, lodging, excavations, cigarettes, admissions and rental equipment, and administers the City’s real estate tax relief program.

VPAP for Francis Xavier King


Treasurer – 4 Year Term – November 2021

Barbara Carraway is a Republican.  She was elected in 1990. She faced no competitor in November 2017.

Salary $135,000 according to data from 2015.

The Treasurer’s Office is the official collector of the City’s receivables. It is responsible for collection of personal property taxes, real estate taxes, stormwater fees and solid waste fees. In addition to collecting taxes, the Treasurer collects other delinquent fees such as delinquent library fines, emergency medical services fees, delinquent terminated water accounts, parking tickets, and miscellaneous invoices. The Treasurer’s Office is also responsible for investing the City’s money and reconciling City bank accounts.

The Treasurer’s Office also issues animal licenses, passports, and hunting and fishing licenses.

VPAP for Barbara Carraway 

VPAP does not show incoming campaign donations for Barbara Carraway, but rather lists her a contributor.


Virginia Governor, Lt Governor, US Senator, Attorney General – November 2021

The next Virginia Governor’s Race will be November 2021 and will include a race for a Lieutenant Governor and Attorney General as well. US Senators serve six year terms. One of the two Virginia US Senator positions currently held by Democratic Senator Mark Warner will be also be on the ballot. He previously served as the Governor of Virginia.

This will yield a higher turnout election for the Chesapeake Constitutional Officers positions open of Commissioner of Revenue, Sheriff, Treasurer and Commonwealth Attorney, but in the last election there was no competition for these well paid positions in Chesapeake.

There are no term limit sets on the Virginia General Assembly, US Senators, US House of Representatives or our local elected officials. Interestingly Virginia is the only state in the nation that prohibits it’s governor from seeking re-election. Governor Ralph Northam, the current Virginia governor, who started his term in 2018, is only permitted to serve one four year term.  Technically, he may run for Governor again in the future, but may not do so consecutive years back to back.

The bottom line is that is your fair warning that there will be an excessive amount of political commercials bombarding us in the fall of 2021! 

Of course there is also the United States Presidential election that will be happening on November 3, 2020. The majority of our state and local elections will not be on that ballot. Since our state and local elected officials greatly impact the quality of our lives, it is critical that we participate in these smaller elections and encourage others to vote!

Contact Information for Local Political Parties in Chesapeake, VA


Chesapeake Republican Party

Typically have a monthly meeting at Chesapeake Golf Club at 1201 Club House Drive, Chesapeake, VA 23322.  Annual membership dues are $30.



VPAP for Republican Party of Chesapeake


Chesapeake Democratic Party

There is typically a monthly meeting at Rivercrest Community Center 1001 River Walk Parkway Chesapeake, VA, 23320. Annual membership dues are $25.


VPAP for Chesapeake Democratic Party


Tidewater Area Libertarian Party



Local Meetups:

VPAP for Libertarian Party


Hampton Roads Green Party

There is typically a monthly meeting listed under events on their Facebook page at the Russell Memorial Library at 2808 Taylor Rd, Chesapeake, VA 23321.


VPAP for Hampton Roads Green Party