Diana Carpenter

Background: Diana Carpenter is at the end of her first four-year term as village trustee. She is self-employed, has managed multifamily buildings for more than 15 years and has been a past director with the Oak Park Residence Corporation and a member of the Building Owners and Managers Association (BOMA). In addition to her extensive involvement in multifamily housing issues and organizations, Carpenter has also participated in a number of initiatives and organizations that involve the West Side. She served as president of the Austin Boulevard Alliance, and is a founding member of Oak Park Court Advocacy. She started her career as a high school teacher and she has a bachelor’s degree in teaching from Ottawa University in Kansas. She is running on the Oak Park First slate, selected by the Village Manager Association.

Priorities: Carpenter lists the top three challenges for the village board as:

1) continued strong police and fire departments,

2) continuing financial challenges and

3) development opportunities throughout the village.

She first took an interest in running for village president at the end of her third year, saying the board process had become a “revolving door,” where “no decisions were being made.” She says Oak Park has come to expect too much from village presidents, and that she would like to distribute more duties to trustees, which she said would offer them a more rewarding experience, and would help issues get resolved in a more timely manner.

She actively supports working with state and federal legislators to help secure funding for Oak Park, and she was one of the first trustees to go with staff to Washington, D.C., to lobby for Oak Park’s interests. She is enthusiastic about Crandall and Arambula’s downtown plan, especially about the proposed public plaza at Forest Avenue and Lake Street.

Quote: “I can’t stand not having decisions made. We’ve got to get things off the table. … Some people [on the board] care more about having their picture in the paper. We’ve got to shift our focus. This is not about me. We’re losing [federal and state] funds left and right. We’re at a crossroads.”

Robert Milstein

Background: Robert Milstein is at the end of his second year as a sitting village trustee. Prior to being elected on the Village Citizens Alliance (VCA) slate, he served on the Citizens Police Oversight Committee and the Community Relations Commission, as well as the Diversity Task Force. He was involved in Black-White Dialogue and the Vote Yes Campaign.

He is currently co-chair of the village board’s finance committee and is running on the New Leadership Party slate. Milstein is a fundraising consultant and has a B.A. in communication from Arizona State University and a B.A. E.D. in government from the University of Arizona. Because he is in the middle of a 4-year term, if Milstein is elected, he would have to appoint, with the support of the board, a replacement.

Priorities: Milstein lists the top challenges facing the board as:

1) supporting economic development growth in business districts throughout the village,

2) high taxes, and

3) transparency in government.

To address these issues, Milstein supports the village making greater use of the Oak Park Development Corporation, and possibly the creation of an “economic council,” which would advise the board on “economic development policy and implementation.” He believes growing the tax base through economic development will not sufficiently help reduce the tax burden on residents, and says the village needs to keep “budget expenditures as low as possible,” and possibly make cuts “at some level” in services. Milstein also said the village board holds too many executive sessions and committed himself to a more open style of government.

Quote: “Oak Park would have to build the Sears Tower to give any significant tax decrease. The state is the key to tax reductions. We need to lobby to end tax caps. I don’t really think the course of government is going the way it should. We need to do a reassessment.”

David Pope

Background: David Pope has served two years as a village trustee and is currently co-chair of the board’s finance committee. Prior to being elected on a VMA-selected slate, Pope was a member of the Plan Commission. As a board member, he pushed the board to complete a master plan for downtown. Pope runs his own management consulting firm, but previously worked as a principal with Price Waterhouse. He has a BA from the University of Vermont and an MBA from Northwestern University’s Kellogg Graduate School. Locally, he is an advisor to Oak Park-based Seven Generations Ahead, an organization dedicated to social, economic and environmental sustainability. He also served as a Peace Corps volunteer, and is a founding member of R.A.I.N.N., a national hotline for victims of sexual assault. Because he is in the middle of a 4-year term, if Pope is elected, he would have to appoint, with the support of the board, a replacement.

Priorities: Pope says the top three challenges facing the village board are:

1) leadership and governance,

2) responsibility, and

3) civility.

The village board has not taken a strong enough role in directing policy, and has “at times relinquished [its] responsibility for charting direction for the future of the community to [village] staff and others, without fully understanding the implications.”

He also said the board has made decisions too often without considering how those decisions affect essential characteristics of Oak Park, such as economic diversity. He believes the board “doesn’t know what it doesn’t know” and doesn’t always ask critically important questions. He is running as an independent candidate, in part because he believes that “raw politics” have had a negative effect on decision-making.

Quote: “We shouldn’t be running the village like a Podunk nonprofit. We’re making decisions on an ad hoc basis. We’re focusing on really minor issues, rather than considering broader policy implications.”

Join the discussion on social media!