The Healy File

For Olivia — About This Recording

Recorded: October 9, 2025 

Olivia,

By the time you listen to this, you won't remember the day it was recorded. You were only about eight months old, and none of this will be part of your memory the way it will be part of your heart.

On this day, your dad sat down and talked about your mom, Katherine Holbrook Healy. He talked about the first time he saw her across a room at a real estate event in Chicago,he talked about the way her laugh was contagious, about the private language the two of them invented together — the nicknames, the inside jokes, the Holby Dictionary — and about the night in a jewelry store in Dublin, Ireland, when he got down on one knee a little unexpectedly and she answered, without hesitation, duh.

He talked about finding out you were coming. About the cupcakes that revealed you were a girl. About how your name — Olivia — was your mother's choice, and it was perfect from the start.

He talked about the devastation, too. About the morning of January 21, 2025 — the day you were born and the day your mom died — and what those first weeks were like for him: the shock, the grief, the work of learning how to be your dad while carrying the weight of the most profound loss of his life. He was honest about how it wasn't instant, the falling in love with you. He told you that too, because he wanted you to know the real story, not the easy version.
And then he talked about how it shifted one night as he was rocking you to sleep.

What you'll hear in this recording is a man who is grieving and grateful at the same time. Who misses your mother every single day and also wakes up happier than he ever has been. Who still feels her with him — especially at church, a place he started going more after she died. He doesn't fully understand it yet. He just knows it's real.

A few things he wanted you to know about her, in his own words: She had a smile that you noticed first. A laugh that, once it got going, pulled everyone around her into it. She loved karaoke bars, carnivals, and novelty in any form. She always got all the fixings — guacamole, the works. She organized every party. She was loyal to her friends in a way that made people line up to do things for her in return. She worked incredibly hard. And she loved fiercely.

Every time your parents celebrated something, they had champagne and pizza. That started in Dublin, the night they got engaged, at a little place called Pacino's. You should carry that tradition forward if you want to.

By the time you're old enough to listen to this, your dad will have had years to tell you about your mom in person. But this recording exists because memory is imperfect and moments don't always keep. On October 9, 2025, eight months after the hardest day of his life, your dad sat down and talked about your mom. This recording is the proof that she was loved — and so are you.

I can't wait to meet you.
-Ashley Adamson

What is The Healy File?

Recorded with love October 9, 2025, in Chicago.