Rocky Caylor


Candidate Name: Richard “Rocky” Caylor

Office Seeking: Mayor

Subdivision with Zip Code: Pilgrim Addition, 60563

Campaign Website:

The following answers have only been formatted for purposes of this website. Answers submitted by candidates have not been edited for grammar or content. 

1. When and why did you first decide to run to serve Naperville City Council?

November 2018. I decided to run because I am concerned that the community that attracted us and so many families to move here is at risk. We are at risk of becoming Chicago where the mayor calls all the shots. We need to get back to an open, welcoming atmosphere where we as a community set the vision and chart its course.

2. What quality and/or skill set will you bring to a nonpartisan 9-member City Council? 

The same collaborative processes I have used building a successful logistics company will serve me well as mayor. I build teams, evaluate the risks and rewards, and implement a winning strategy.  I understand that running a successful business or city requires a sharp eye on finances and a Continuous Improvement process. Additionally, I have extensive legislative experience both on the State and National stage. I plan on bringing this experience and vision to the position of mayor.

I believe Naperville is better served by working with residents, council and staff to build a community vision, not pushing an agenda on Council and this city. I want to take council deliberations to a higher level where everyone is comfortable expressing their views and learning from each other. It will be a more relaxed, deliberative and representative body than what we have today.

3. What do you consider to be the three biggest issues facing the City today?

Take Care of Our Residents

I’ve become increasingly aware that, even in Naperville, there are far too many youth and adults dealing with drug addiction, mental health issues, and disabilities, as well as those who don’t feel totally welcomed by the community.

Ensure Wise Development

Another major concern is how new developments impact residents. Going forward I will ensure that any new development is compatible and complementary to nearby residents, which is something that hasn’t always happened in the past. We suffer from significant traffic congestion today. We must try not to make it any worse. In addition, we must consider seniors and first-time homebuyers in our housing development decisions.

New Master Plan

Naperville’s master plan is woefully out of date, and while Naperville is largely built out, we need to update our plan to reflect the built environment and direct how we envision future development.

4. Realistically and fiscally speaking, if you could change/improve one thing in the City, what would it be? 

Here’s an attainable goal. I believe Naperville can, and must, become a leader in new internet technologies and renewable energy by investing in the necessary infrastructure to assure that Naperville continues to be an attractive community for businesses and families.

5. What do you think the City Council could do to help keep Naperville affordable for homeowners of all ages?

There are no easy answers here. Teardowns have significantly reduced the number of modestly priced single family homes in the downtown area. Naperville does have a fair number of modestly priced townhomes, and there is the potential to place a certain number of reduced priced apartments/condos in the 5th Ave redevelopment area which could help with our current noncompliance with federal guidelines. I would be interested in looking at other communities to see if there are creative, thoughtful ideas being implemented elsewhere.

6. What City amenity is most important/attractive to you and how should its care and maintenance be funded?

The establishment of the Riverwalk created both a wonderful amenity for residents and was also an important component of the revitalization of our downtown. It truly makes our downtown something unique and special. Residents and visitors alike, appreciate its family-friendly atmosphere. My understanding is its maintenance is the responsibility of the Riverwalk Commission who receives funding from the City of Naperville and the Park District with the Park District performing the work. I believe the current arrangement is working out satisfactorily.

7. What should be done about the Special Events and Cultural Amenities (SECA) fund, if anything?

This program needs to be revisited. It is my understanding that the SECA Commission has been tasked with examining the current program and making recommendations for restructuring. I would advocate for returning it to its original purpose, covering the cost of city services for special events (like parades and community festivals) and sponsoring unique cultural amenities (like a visiting artist or special theatric presentation). I also think it’s time to examine using this fund for capital improvements of some of our current cultural amenities (like the anticipated Carillon improvements) or a new cultural amenity (perhaps more public art or an art gallery). To me the key purpose is to enrich the quality of life for our Naperville residents; that is the question that each grant should answer.

8. What can the City of Naperville do better to retain and attract businesses that encourages development? 

When elected I will advocate for the City to establish community resident/business working groups for other locations in Naperville such as an Ogden Corridor Group, a 95th Street/Route 59 Group, and a Wheatland Industrial Park Group. These groups would be similar in structure and operations as the Downtown Advisory Commission (DAC).

The groups would be a mix of city officials, property owners, business representatives and residents who would apply to be appointed to serve with a commitment of valuable time to meet and assess the needs/wants of the area in a useful, reasonable and purposeful manner early in the process.  I will assist with building teams of representatives from each group to bring issues, best practices and successes together to connect and keep the city informed.

9. Are you a proponent of Tax Increment Financing (TIF)?    NO

10. Do you live in School District 203 or School District 204? D203

Please tell anything else that distinguishes your interest in serving Naperville in 150 words or less… 

I see the position of mayor as a champion for the city, and one of service, two of my greatest strengths. I enjoy bringing teams together on a transparent level to achieve our common goals. Something I have done at the local, state, and federal level.

If you look at the many charitable organizations and activities that I am part of, and in many cases have created, you will see my commitment to serve people of many different stripes. Naperville is a wonderful, family oriented community, but like all communities, we have our challenges. I want to bring this community together and be a community of purpose where we all respect and help each other.

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