Christopher Bester is a big dude — 6’4”, 350 pounds, to be exact. But one of the key principles of the work that he does, keeping people, environments and events safe as founder and CEO of Legacy Protection Services, is de-escalation. “Our team is trained to manage situations calmly and respectfully, preventing incidents from escalating whenever possible. We understand that that is another human that we are dealing with,” Bester tells Madison365 in an interview at the Black Business Hub in the heart of Madison’s South Side. “At the end of the night, I have a family, and I want to make it home, and I also want to see them make it home.”
Bester launched Legacy Protection Services in October of 2025 with the mission of helping create safer environments for businesses, patrons, and the broader community here in Madison. He leads a team that currently provides security services for five popular establishments in Madison, including Merchant, Lucille, Tavernakaya, Cafe CODA and Casa Zaragoza Mexican Restaurant.
“Our goal is not only to respond to issues, but to proactively prevent them by promoting accountability, communication, and respect across all venues we serve,” Bester says.
Legacy Protection Services recently provided security and support on May 6 at the historic grand opening of Rev. Dr. Alex Gee’s new building, The Center for Black Excellence and Culture. Bester says that they served over 1,537 people throughout the event and that it was “a major milestone” for his company.
“It is an honor to be working for the Center for Black Excellence and Culture … man, it’s going to open so many doors for my company. That’s a big, beautiful building and Rev. Alex [Gee] really did a great job. He showed out,” Bester says, noting that Gee is also his Godfather. “Rev. Gee also encouraged me and pushed me to open my business, as well, and I really appreciate that.”
As one of six siblings growing up in the heart of Madison’s South Side, Bester says that he learned early on how to navigate challenges, communicate effectively, and take responsibility. Bester grew up on 1862 Fisher Street, right down the street from Mount Zion Baptist Church and really close to the Boys and Girls Club on Taft St., and what is now the Black Business Hub, One City School’s pre-school, and The Center for Black Excellence and Culture.
“This is my neighborhood and I love to see these new buildings go up. Even the building we’re sitting in right now [the Black Business Hub], it used to be a gas station, and I would bike over here as a kid to grab snacks,” Bester remembers. “So to see this area build up and really have all these nice modern buildings is amazing.”
Bester says that he has been part of his Madison community his entire life, and that helps to make the commitment he has to his security work deeply personal. His father was involved in the NIP (Neighborhood Intervention Program) and worked as a social worker. His mother provided childcare in her home and volunteered extensively with the Boys & Girls Club.
“Growing up in a household that emphasized accountability, service, and community shaped the values I carry into my business today,” he says.
“Security’s job is to do what they’re told to do in their procedures and policies, but going the extra mile of being human is important,” Bester adds. “I feel like I’ve learned some valuable lessons about that from my father, James Bester, and my mother, Sherry Bester … they taught us all the time that you should be able to fit in the room with a Black person, white person, orange, purple, green, blue, Mexican, Chinese, poor, rich, etc.”
Bester has been in the security business for a long time.
“I’ve been doing security since I was 17 and getting into different types of security like personal events, just those kinds of things, and then the bar scene, of course, when I got of age,” Bester remembers. “Over the years, I’ve just never thought to myself that I could actually run a security company … that this is something that I can actually do. But in October of 2025, I took a risk. I was like, ‘You know what? I’m just gonna shoot for it.’ And I got the LLC.”
Bester launched Legacy Protective Services with the tagline “Safety is paramount” and says he is grateful to have received early support in his journey from Mike and Hilary Brandt, who sponsored him and helped jump-start the foundation of this business. Bester also has high praise for Legacy Protection Services CFO Jordan Fox, who is both a mentor and strategic partner collaborating with him on many of their projects. “Together, we are working toward long-term growth and meaningful impact,” Bester says.
“I took a risk with this business and I just launched off, and so far it’s been going great. I work with different types of people and different types of crowds,” Bester continues. “I have bilingual guards who can speak English and Spanish. Communication is something that has always been very important to me. Process and procedure are also very important to me.”
Bester says that when serious incidents occur, such as fighting or unsafe behavior, Legacy Protection Services thoroughly reviews the situation. If necessary, individuals may be restricted from entering any of the venues they serve. But the Legacy Protection Services’ process also includes an opportunity for a restorative conversation, where individuals can gain a clear understanding of expectations and accountability moving forward.
“We live in challenging times and there will be difficult situations that are part of the job,” Bester says. “I’m willing to have a restorative conversation with people as long as their offense wasn’t super egregious. I’m always very professional.”
By maintaining communication across venues, he adds, his team can “stay aligned and consistent in enforcing policies.”
“I love to serve people. I love working … even in those challenging times. I know how to deal with them, and I know how to be fair. I try to be understanding. I work with children [during the day], and my expectations for kids are the same thing. I see a lot of similarities in my jobs because drunk people and kids seem to know everything,” Bester laughs. “But I have those expectations for adults, drunk or impaired or not, that I have with my kids. We have firm expectations all across the board.”
(Photo by A. David Dahmer)
During the daytime, Bester is a student support specialist at One City Elementary School, where he is sometimes called upon to deal with challenging situations calmly.
“Right now, I am currently doing a Scholars Academy class. It was needed, so I stepped into the teaching role, and it’s been going great. That program is awesome,” Bester says. “That program really gives the kids a second chance. I’ve been at One City for about five years now, and the beautiful thing about my job is that I get to see the growth in the young students and why that program matters.”
Bester has been working with kids since he was 13 years old, he says, starting at the Boys and Girls Club of Dane County. “I’ve been working with those kids who are typically a challenge for others. But I always want a challenge,” he says. “I don’t want anything that’s easy in life.”
Whether it’s a challenging child going through a rough patch in life or a challenging adult drunk person after hours, Bester knows that communication, accountability, consistency, and trust are the keys to a successful outcome.
“The biggest thing for me when I’m working is to not take things personally and that is the biggest thing I want for my guards, too,” Bester says. “Security is a needed thing. But I think outcomes are much better when you have somebody who is connected with the community rather than having a third party who is not from here.”
The old adage still rings true that “nothing good happens after midnight.” Challenges often arise, but incidents rarely escalate to the point where law enforcement involvement is required.
“So one of the great things, too, is that I have relations with the Madison Police Department and they do a great job of surfacing downtown around that exiting time,” Bester says. “I’ll call them, and they’ll be outside the venue, just to make sure it’s a smooth exit, and no one’s carrying stuff on or partying outside the venue. It really helps.
“They are being proactive instead of reactive. We don’t want to be reactive. That’s not a good state to be in. That’s not a good strategy,” he adds. “So we plan ahead, and we do our best with aligning our mission and using the resources that we do have.”
Bester says that his goals moving forward are to keep building systems and relationships that contribute to a safer and more positive late-night culture in Madison.
“I want to keep growing my company. That’s my goal. Long term, I would like to get into more buildings, especially buildings over here on the South Side. I just love my community,” Bester says. “But I believe that I can create safe building procedures for every building. But also, I take pride in this space, and I really want to move away from the bar scenes and get into more things like apartment complexes or places like the Urban League or the Black Business Hub.
“We do have some great things in the works and some very good projects coming up. I can’t wait to share more as they happen,” Bester adds. “I want people to know when they see Legacy Protection Services, that we deeply care about them and that we care about their safety. That is my number one thing.”
