Orlando Bailey was the first person I hired to help build BridgeDetroit, even before we launched in the spring of 2020. 

That decision was a no-brainer.

His experience organizing and building at the Eastside Community Network; his vast connections; how he’s as easygoing and genuine on the cracked cement at a neighborhood barbecue as he is in the plush-carpeted suites of executives; his easy and warm welcome, extended graciously across so many corners of our Detroit lives. 

It was precisely the right mix of experience and skill we needed to create the engagement profile for BridgeDetroit. 

Orlando instantly rejected what he called transactional engagement (periodic contact with Detroiters to ask them about OUR concerns) and insisted that BridgeDetroit needed to build relationships with Detroiters – deep, abiding relationships, centered on citizens’ lives and concerns. 

So we did. 

BridgeDetroit has a complex and consistent engagement protocol that reaches thousands of Detroiters every year, and the feedback from that engagement frames the work of our newsroom. 

Our approach is broad and multi-faceted. And it has paid grand dividends to our mission serving Detroiters: in 2023, for instance, our staff knocked 3,000 doors to reach out to Detroiters, and grew our base of subscribers to more than 30,000. 

So much of our success, in the short span of four years, owes to what Orlando imagined, what he dreamed, and how that figured into the design and execution of what BridgeDetroit has become. He also led with love, all the time – love for our staff, for our organization, and for our city. 

But no one stays forever; Orlando’s four years as BridgeDetroit’s engagement director is virtually an epoch in modern journalism. 

Opportunity knocked, and he answered: He will become next executive director of Outlier Media, an important BridgeDetroit partner. 

We will miss him terribly. He is the last of the original hires at BridgeDetroit, and one of a kind. His work, though, continues with fervor through the infrastructure he leaves and the tremendous talent we will call on to fill the void. 

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Henderson is a native Detroiter who has nearly 30 years of journalism experience as a writer and editor, and a deep-rooted connection with the city that birthed him. A winner of the Pulitzer Prize,...

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