Jamel Brinkley, Upper School Teacher of English from 2009-2013, has a story, "Comfort," featured online in the summer 2020 issue of Ploughshares, an award-winning journal of new writing. He is the author of the acclaimed short story collection A Lucky Man, the recipient of numerous honors including the 2018 Ernest J. Gaines Award for Literary Excellence, a finalist for the 2018 National Book Award in Fiction, and a finalist for the 2019 PEN/Robert W. Bingham Prize for Debut Fiction.

Jamel Brinkley left Trinity at the end of the school year to attend the Iowa Writer's Workshop. During the end-of-year luncheon, Upper School Principal Jessica Bagby gave these remarks: "Jamel, as both English teacher and English chair you have deeply enriched our common life. We are thrilled for the opportunity you have to pursue your calling at the Iowa Writer’s Workshop. We hope you won’t be a stranger and that you will let us know, despite your signature modesty, when we can expect to see your name in print. Thank you for your contributions to our community."