San Jose City Attorney Rick Doyle announced this past week that he’s retiring after more than 20 years with the city of San Jose. Doyle was appointed to chief counsel in January 2000 and plans to officially step down on Aug. 8.

San Jose Inside recently caught up with Doyle to talk about his two decades of service for the nation’s 10th largest city. Here’s a transcript of that conversation.

What’s been the highlight of your career with the city? 

It’s hard to pick one because there’s so many things that go on. I think working with the various mayors and city councils each has had their own agendas and priorities. I can’t say anything’s career defining as much as you learn with various issues.

When I first came in, the San Jose airport curfew was a major issue. It got tied up in the courts, it got thrown out and it was a big community issue to keep it in place. We had to negotiate with the FAA and put in a new curfew, and that wasn’t easy because the federal government wasn’t too keen. The FAA doesn’t like restrictions like that.

We were able to successfully negotiate and you learn working with various consultants and agencies of the importance of patience and it takes a while for things sometimes to get done. We did that over an 18-month period. We were flying back to Washington D.C. quite a bit in the old days of face-to-face meetings.

The pension reform came around and while we weren’t directly involved because we had conflicts (we were members of the pension plan and outside counsel was used). Obviously, we were all engaged as employees and managing through it. It just showed the disruption that can happen in an organization. It wasn’t just the economy and having to lay people off, but just the strife between labor organizations and city management.

I think we’re still recovering from that, in some respects, but a lot patience was necessary to try to work through some of those. I think, in the end, in hindsight, a lot of things could have been negotiated and worked through without court battles.

How has the city changed over the last 20 years?

I think the city’s evolved. We’re a little more big city-ish. San Jose was a million people by 2010. We have a lot more big city issues, whether it’s organized groups that want to influence city government, whether you call it business or labor.

I think the issues of affordable housing, which were front and center in 2000, are still with us today, but I think the approach is much more we’ve got to find a way to deal with this and we can’t displace people.

Whereas in the past, I think it was trying to find housing but it wasn’t necessarily going to stall a project. We built 10,000 units in the first decade, largely with redevelopment money, and trying to build on that is the goal, but it’s easier said than done.

I think the equity issues that’s coming front and center, those have got to be addressed. The city government and the relationship with the citizens I think is much more engaged and you see that more in large cities.

What’s been your biggest challenge as city attorney? 

I think it’s trying to keep the city running. You get some pretty controversial things that come forward whether it’s in the form of a proposal from the council to some type of policy shift. There was a major effort in the 2000s with the converting of industrial lands to residential to help build more housing. Then there was a 180-degree reversal on that, where we wanted to preserve industrial land because the jobs to housing imbalance was out of whack. That was sort of a major undertaking at a policy level.

But the police cases probably get bigger headlines—especially now.

Pension reform was also a huge issues and it’s probably going to still continue to be a huge issue for the foreseeable future. Just trying to get through the fiscal issues can be challenging, especially during recessions or during COVID recessions.

Being the city attorney is really about trying to keep things moving forward and helping to advance policy goals. Then there’s just what I call the day to day business of the city, everything from employment issues to policing.

What are you going to miss most about working at the city? 

The good people. My staff, to begin with, I think is top notch. There hasn’t been a day where I’ve not wanted to go to work. Virtual work seems to be OK now but I miss the office environment. I think the people in the city are dedicated. You miss that, but there comes a time where you realize it’s move on. Twenty years is a long time in this business. My total years with the city is 26, but as city attorney it’s been 20.

What would you like the public to know about the city attorney’s role?

Our job is really to help the city move forward within the parameters that the law allows. We’re sort of in the background, but clearly we’re working with the policymakers and the city officials on a daily basis to try to keep things moving.

It’s a great job.

It’s very interesting in terms of the types of issues you see, but I think it’s a challenge because you’re dealing with all sorts of various issues whether it’s lawsuits coming in against the city, whether it’s people trying to bring initiatives forward and then you have competing interest and just making sure the process is fair and people are following the process. I can’t say anything other than it’s a good job and the issues are fascinating.

Answers have been edited for clarity and length. Want to nominate a subject for a Q&A? Email the author or leave a suggestion in the comments below.