Copyright Boston.com
About five years ago, James “Jimmy” Hills started an impromptu livestream on Facebook to chat with community members about the COVID-19 pandemic and how it could disproportionately affect people of color in Boston. The desire to engage with the community was natural for Hills. A native of the city who grew up in the Bromley-Heath Housing Development, Hills said he experienced bullying at a young age that fostered a commitment to advocacy. He later went on to work as a special assistant to Mayor Tom Menino and has done extensive work pushing public officials to take action to reduce street violence. The interest was there when Hills started his livestream, and he returned to the microphone every day. Now Hills, 54, is one of the most influential people in Boston, and “Java with Jimmy” is essential viewing for many. Hills is an adviser to Mayor Michelle Wu, who calls into the show once a month. Hills does not shy away from engaging with politics, interviewing people like Gov. Maura Healey and Rep. Ayanna Pressley. But he also interviews community organizers, mental health experts, faith leaders, and artists. Often, Hills’s shows revolve around his simple engagement with a group of dedicated viewers he affectionately refers to as the “Java Fam.” When Hills reflects on the five-year anniversary of his show, this community seems to be what he is most proud of. Boston.com recently caught up with Hills for a conversation about the show’s history, whether or not he views himself as a journalist, his potential political ambitions, the next five years of “Java with Jimmy,” and much more. The following interview has been edited for length and clarity. Boston.com: How have you changed since you started doing this five years ago? Do you see yourself differently? Do you think about your role in the community differently? Hills: I have changed a lot in the past year. I’ve changed a lot. I always see myself as being a catalyst and a sort of a compilation of voices for the community, and I don’t always do that well. Because there are some folks that disagree with what I’m saying, but I tend to try to go with the majority. And sometimes, being a public figure, that comes with critique. I have done it with elected officials and community leaders and whatnot, and so some of that reciprocity has come back. What I mean by the changes: You as a human, you do kind of look in the mirror and say, “Well, like, what the hell? What am I doing wrong?” And I did a lot of self-examination starting a year ago. Because of the platform and a lot of the things that I do, I take on a lot of the community’s issues, because I don’t hang up from a phone call or Zoom and have that issue just go out of my head. I had to do better at self-care in the last year. I did a lot of self-examination about what’s wrong with Jimmy, and how he can improve his character, his integrity. All the things that I’ve changed and went through have really made me better poised to advocate and use my influence toward equity. What do you do to decompress? Ideally, I hit a beach and I watch a sunrise. But I also decompress by eating. I’m a foodie, I joke about my self-care being expensive. I love oysters, I love espresso martinis, I love crudo, I love sushi. I’m also intentional about going on “Do Not Disturb” often. Generally I’m very accessible, and sometimes with that accessibility comes a lot of weight, and so often, I take the weekends, and I put my phone on DND, I’ll text my mom and everybody before I do that and check in, but it’s really to take time to myself and do deep thought. And I watch, you can put this in quotes, I watch “ratchet TV.” Ok, I need one restaurant recommendation, and one TV show recommendation. Definitely Grace by Nia. And then for the show — either “Baddies” or “All the Queen’s Men.” I know your show started very informally, was there one moment where it all clicked, and you realized this was actually going to work? It was the combination of moments, like when people inboxed me and said that they got the COVID vaccination. Often people would comment and say that because we were in lockdown, that they didn’t have a sense of community. People started commenting about how they’re appreciative of a platform, where they can gather every day. Maybe six to nine months in, I knew that I had to continue to hold the space, and I knew that we were having impact. I wouldn’t have continued that long, or up until this day, if I could not point to any impact. Do you see yourself as a journalist? Honestly, I’m not going to give you a “yes” or “no.” I struggle with it. I consider myself to be a community voice. It started with getting out accurate information about COVID. That’s a form of journalism. And with this election, the influence from D.C., and half-truths, and things about White Stadium, and about the mayor, and the white poles, and the street bumps. When I see a lot of the inaccurate information, I do have a little extra energy about getting the accurate information out there. One of the reasons I struggle with journalism is because I want to be accurate as hell. I say I’m a community voice-slash-community journalist, to answer your question. You’ve been doing community organizing for a long time, but tell me about the past five years and the community that you’ve built around the show. One, it wasn’t intentional. Two, it grew into a family through consistency. We gathered every day for the first year. Every single solitary day at 9 a.m. It happened organically. This family came together at the worst time in our generation’s history. Out of that bonding, and the consistency of the platform, we did form a family. Another difference is that I’m at the helm. I have the weighty, awesome responsibility of shepherding this audience and this “Java fam,” as I often refer. There’s an accountability that I feel not just to them, but to the community. Do you feel like the practice of doing the show is therapeutic to you? Or is it more like work? It’s both. This has become such a part of my life. It is therapeutic for me because I’m a servant at heart. This is my active form of service right now. There is work — scheduling the guests, doing the flyers, answering questions, looking at the comments, creating content. You see a 30-second reel, but that took about an hour to create. I’m an entrepreneur, but it doesn’t feel like work. There’s work to do. But I don’t view it like a job and work. Maybe I should. It’s service, and it’s giving back, and it’s keeping our community healthy as much as I can. Would you ever run for City Council or another office? As of right now, I would not consider running for office unless I see the landscape of the candidates continue to diminish. I don’t think that’ll be the case. I think that there will be a lot of people who are viable. Who, though not perfect, have the success of District 7 in their mind. I don’t want to feel like I have to run. So I don’t have any considerations of running for any public office as of right now. However, if I ever feel that the voices of those that I serve are not being reflected on the council or in the State House, then that’s a different conversation. How do you think about the future? What’s next for “Java with Jimmy”? I want my own platform. What I mean by that is, I want to be a sort of BET or a Revolt. I want to be a platform where I help the next generations of me and give them a platform. They may not have all the tech and whatnot, but if they can show up, and I record for them, or they bring a guest, I will do that. I have an aspiration of something like “Java with Jimmy Studios.” I do want a building, to be able to have my audience come into the show. But I then also want a building where when the show’s over, there can be community meetings. The mother’s board can come and crochet, cook, have a book club. You’re not burnt out, you’re not going to call it quits anytime soon? No … I’m committed to this. My commitment was renewed in November, my commitment was renewed in January, because we have a COVID-type pandemic that is active in D.C. right now. I do feel my responsibility to keep the community informed, to raise awareness. My commitment to this is being reinvigorated … I’m here for a long haul.
