Meet Orlando Bailey — Outlier’s new executive director

On Monday, June 3, Orlando Bailey officially started at Outlier Media, taking over as the executive director. Orlando was previously at BridgeDetroit , where he spent four years building a successful community engagement strategy. I plan on staying on as executive-at-large until August 9.

This marks the beginning of an important transition for our organization, as we work to deepen our local community relationships and continue to increase the sustainability of our newsroom.

In the coming months, we hope you’ll have the opportunity to get to know Orlando better. Come meet Orlando at Mocktails in the Garden on Friday, June 28, from 6 pm – 7:30 pm. You’ll enjoy handmade mocktails from Castalia at Sfumato, small bites, and connect with other members of our community. We hope to see you there!

We’ve asked Orlando a few questions so you can learn more about our new co-leader. Check it out below.

Candice: What makes you excited about this role at Outlier?

Orlando: I’m excited about the role because it is paramount for news organizations based in Detroit to have Detroiters leading them. Living in the city we report on adds an additional layer of accountability. At the end of the day, we go home and face our neighbors to be held accountable for our work. There is also this double consciousness of reporting on issues that we are also experiencing directly as residents.

To be positioned to lead a newsroom that is a national innovator at getting news and information to people who need it most is a huge privilege. I’m excited to be able to cast vision. I think that news media and journalism are the last stop for us as a nation to be able to face and tell the truth in a climate of massive erasure of whole communities, histories, and works of literature. I believe we exist at this particular time to literally tell the radical truth. Lastly, I believe it’s paramount for Detroiters to see themselves in the news organizations telling their stories, especially our young people. In order to build a viable talent pipeline for this industry to survive, young people have to be exposed to what we do. Young people can’t dream about becoming something they’ve not been exposed to. I hope my being at Outlier inspires that.

Candice: Do you have a favorite book or piece of media that centers Detroit?

Orlando: I have multiple! I think what is required reading for anybody wanting to do work in Detroit is The Origins of the Urban Crisis [by Thomas Sugrue], which was the first book I read when I started my career in community development years ago. Another book I loved is The Making of Black Detroit in the Age of Henry Ford [by Beth Tompkins Bates]. The book When Crack Was King [by Donovan X. Ramsey] talks about Detroit a little bit, and I don’t think we can look at the physical landscape of Detroit right now and not talk about the crack epidemic that ravaged our city at a rapid pace and also ravaged families including mine. I feel close to it in a real way, and I got a lot of insight around what happened in my family and what happened in my city because of this debilitating addiction. It’s my most favorite recent piece of media that I’ve read and Donovan X. Ramsey is an incredible journalist. Black Bottom Saints [by Alice Randall] is so much fun. I can go on and on!

Candice: Where is your favorite place to relax in the city?

Orlando: My most favorite place to relax is Lafayette Central Park. I walk through it multiple times a day because I have a dog, Coco Michelle Bailey, and her walk time is non-negotiable. Those walks have become so regenerative to me, and I get to fill my cup while she empties hers, haha.

Q : What’s the best thing you ate or drank in Detroit in the last year?

Orlando: The black shells pasta at San Morello.

Candice: How can Detroiters connect with you?

Well, I’m really excited to connect with everybody on June 28th at Mocktails in the Garden on the eastside. My first event as executive director will be in the neighborhood where I am from — Jefferson Chalmers — hosted at Detroit Abloom. I’m excited because everyone can come out, show some love, and meet with me there. I’m also on all of the social media platforms, and you can email me at orlando@outliermedia.org .

I want to see you. I want to meet you.

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Meet Orlando Bailey — Outlier’s new executive director · Outlier Media