Charlottesville City Council incumbents outraise newcomer through joint political action committee

There is a three-way race for two Democratic nominations for the two seats up for election to Charlottesville. Incumbents Brian Pinkston and Juandiego Wade are running as a pair and are facing a challenge from newcomer Jen Fleisher. In addition to raising funds individually, Wade and Pinkston have a joint political action committee.

Incumbent Brian Pinkston reported the highest contribution with $100 in cash and $12,672 in in-kind contributions. He began the year with $507 in his campaign’s bank account and ended March with $560 in the bank.

In-kind contributions consist of the financial value of goods and services offered to the campaign. These are listed as $12,360 from the “Wade-Pinkston Victory Fund” as well as a $313 in-kind contribution from former City Councilor Heather Hill.

Anyone can search raw reports at the Virginia Department of Elections at this link. There are two reports for this newly created political action committee.

The Wade-Pinkston Victory Fund reported its first report on January 13, 2025 for activity in December 2024. A political action committee subject to the same fundraising rules as candidates but not directly tied to them. The Wade-Pinkston Victory Fund raised $17,890.44 in December with $1,576.58 in expenditures. The fund had a balance of $16,403.86 coming into 2025.

The top contributor in this period is developer Ludwig Kuttner who donated $6,000. A cannabis retail store called The Hidden Leaf contributed another $2,000 and developer Keith Woodard contributed another $2,000. Another $1,000 came from a transfer from Juandiego Wade’s political action committee.

The second report covers activity from January 1 to March 31. The Wade-Pinkston Victory Fund reported $33,448.82 in contributions during the period. There were $18,881.93 in expenditures leaving a balance of $30,970.75 coming into the second quarter of 2025.

There were two contributions of $5,000. The first came from an entity called 11th & Cochran LLC identified as a real estate entity based in Albemarle County. Property records indicate they are the owner of a building identified as 119-123 East Main Street on the Downtown Mall.

The second $5,000 contribution came from Chris Henry, president of the Stony Point Development Group. That’s the group behind the recent renovation of Dairy Market into a mixed-use development.

Developer Richard Hewitt of Seminole Trail Properties contributed another $2,500 as did ShelterPAC. The Monticello Business Alliance PAC made a $2,000 donation and Keith Woodard added another $4,000.

From this report we learn that Hill covered the cost of a campaign event at $313, the source of that in-kind contribution listed above. Kardinal Hall provided event space for a $200 in-kind contribution.

Actual expenditures went to pay for consulting, marketing, and other campaign funds.

In contrast, Fleisher is running without the benefit of a mate. Her campaign raised $3,675 in a period from March 6 to March 31. That includes a $300 in-kind contribution. Fleisher spent $740 and had a balance of $2,635 at the end of the month.

So far I am aware of two campaign forums for the three-way race that will be the first time ranked-choice voting will be used in an election in Charlottesville.

• The Greenbrier Neighborhood Association has invited all three to participate in a virtual forum on May 14. Details on how to participate as we get closer.
• The Free Enterprise Forum will have an in-person forum at the Hillsdale Conference Center on May 28. 

Before you go: This story first appeared in the April 17, 2025 edition of Charlottesville Community Engagement. For some reason it took five days to upload to here. Want to support it? I’m now routing people to this page.