My Obituary

Trey Whitaker
7 min readOct 18, 2022


Until my father’s passing on the morning after Thanksgiving in 2009, I’d never written anything that could be deemed important. I’d dabbled with writing. I’d taken an introductory course at a community college and penned articles for company newsletters, but none of this really mattered.

My father had experienced some ill health in the month before his death. He’d been in the hospital for eighteen days trying to recover from a variety of issues, but primarily heart disease. Unfortunately, his retirement years had included battles with colon, bladder and breast cancer. At the age of 78, he’d lived a life full of adventure and accomplishments, but decades of firefighting, fatherhood and a lifestyle with the then-typical excesses of eating, drinking and smoking had taken their toll.

He’d been released from the hospital shortly before the holiday and we enjoyed a typical Thanksgiving together. As had long been the case, the holiday was filled with food, football and family. For myself, it felt like the perfect respite after having recently spent nights napping uncomfortably in hospital waiting rooms.

My sister called me in the wee hours of the next morning. That time of the day when you don’t expect good news to be on the other end of the line. My father had suffered a massive heart attack. He’d ventured into the kitchen in the early morning hours to quench his thirst with a swig of egg nog. As the heart attack struck him and he fell to the floor, my father kept his grip on the open carton and the eggnog sprayed in an arcing trail across the cabinets.

My sister said that an ambulance was taking him to the emergency room, but she warned me that things didn’t look good. She was correct.

Not long after we arrived at the hospital, we were pulled into the dreaded private family room. As expected, the doctor informed my mother, my sisters and I that my father had died. My sisters went to see my father and I stayed with my mother. Eventually, I called my brother to let him know and then we drifted back to my parent’s home.

Somehow, we quickly shifted to informing friends, making funeral arrangements and receiving visitors. I sat down at the my parent’s computer to write my father’s obituary.

I’d never written an obituary. I’d never taken a course on writing one. I did a Google search for my grandfather’s obituary and found it online. I also looked at a few other obituaries and found that there was a standard format: Name. Photo. Date Died. Age. Family members. Career and interests. Funeral details. Flower or donation information.

I cobbled together the basics and then began expounding on the legacy of my father. I shared a draft with my mother and sisters for additions, tweaks and corrections before submitting it to the local newspapers.

Link to my father’s obituary: William ‘UU’ Whitaker (1931–2009)

In the years that followed my father’s passing, we remained a tightly-knit family. Without my father, some of our traditions began to change, but only in small ways. The annual Christmas Eve gathering at my parent’s home became a family dinner downtown. A summer vacation at a Rhode Island cottage shifted to an excursion to Bermuda. Thanksgivings were relocated to my sister’s home where I attempted to step in as the new turkey carver. Honestly, I did a terrible job.

My father was always one to be prepared. I think it was the fireman in him. He enjoyed live, but he had prepared for death. He’d even had his gravestone created and installed years in advance of his passing. One summer day, he invited to me to the cemetery to view his gravestone and talked me into buying burial plots nearby. So we could be together. Yet, with all this planning, he’d not written his own obituary. I wondered if he had just overlooked this detail or had intentionally avoided it. Was it bad luck? Was it too much like a suicide note? Did he feel that it was meant to be penned by someone else?

My parent’s gravestone

In 2015, my mother fell ill and landed in the ICU. As family and friends gathered at her side, her condition went from dire to hopeful to tenuous to hopeless. In my mother’s room, my daughter slept on the windowsill, my sister laid magical crystals on her bed, numerous doctors made consultations and all types of wizardly medical machines were deployed, but to no avail.

This time, when I sat down to write my mother’s obituary, I knew what needed to be done.

Link to my mother’s obituary: Patricia ‘Trish’ Whitaker (1936–2015)

During the pandemic shutdown in 2020, I had lots of opportunity to walk through the woods and ponder. I wondered if anyone did as much walking in the woods as I did. I listened to music and created massive playlists on Spotify. I gathered a list of writing prompts that has now reached 776 items. These ideas for writing are random thoughts that I intended to explore ‘when time permits’. You know how that goes.

One of the prompts was this: Could you write your best friend’s obituary? If found that you had missing pieces of information, would you reach out to your friend to learn more about them? Would this dialogue deepen your relationship? Or would they be bothered that you didn’t know?

Since it was the middle of the pandemic, I touched based with my oldest friend. We’ve known each other since meeting in elementary school in the late 1960's. I asked him: Do you feel that I know you well enough to write an accurate and complete version of your obituary.

He said that he felt I could. I was pretty sure that I couldn’t.

Why? I’m not the inquiring type. I’m always interested to learn about people, but only based on what they are willing to share. My father had always promoted the idea of not being nosy and minding one’s own business. As an avowed introvert, this is a concept I was able to get behind fully.

While my life doesn’t appear to be in imminent danger, I’m very likely in the final quarter of my life. I’ve had some health issues in the past, but I’m decently fit for being a 63-year old, two-time cancer survivor with one kidney and a lot of miles traveled. It’s not the end, but it’s very likely the beginning of the end.

The 2009 movie ‘Get Low’, starring Robert Duvall, tells the story of a very unwell man who decides to hold a ‘funeral party’ for himself. The Cliff Notes version of the plot is that Duvall’s character wants to hear the stories folks would share about him. He wanted to know what people had to say.

I’ve been very fortunate in having friends and family share their feelings with me. I literally have books full of kind notes and fond memories. Thankfully, I don’t have any need for or any intention of planning a funeral party.

That said, I thought I’d help my beloved survivors by drafting my own obituary. Note to my beloved survivors: You will need to fill in the blanks and you’re welcome to add, change and delete as you’d like.

Herbert ‘Trey’ William Whitaker III (1959-?)

Trey Whitaker, (age?), of Kihei, Hawaii, passed away (day of the week, month, day year).

The beloved husband of Charito ‘Cherry’ Cruz Whitaker, Trey was born June 29, 1959 in Manchester, CT, the son of the late Bill and Patricia Whitaker, of Manchester, CT.

Trey graduated from Manchester High School in 1977. He was a paratrooper in the 82nd Airborne Division from 1977–1981. In 1981, he began a 35-year career in financial services with such industry leaders as Aetna, Lincoln Financial Group, Travelers, The Hartford and MassMutual. During most of his career, Trey was a leader and a communicator. In 2017, Trey became an owner of Tolland CrossFit until his retirement in 2022. In his retirement years in Maui, he volunteered as a trail steward at Haleakala National Park, as a groundskeeper at the Alexander & Baldwin Sugar Museum and as a member of the conservation team for the Pacific Whale Foundation. Trey enjoyed hiking, photography, writing and time with family and friends.

Trey was a lifetime sportsman and outdoorsman. As a kid, he played Little League, delivered the Hartford Courant and loved a good snowball fight. While in the Army, Trey played third base for the 82nd Airborne Division’s fast-pitch softball team. Upon moving to California in the mid-1980’s, Trey focused on basketball and marathon running. When he returned to Connecticut, he began 20 years of coaching youth soccer and basketball. In mid-life, he took up jujitsu and earned his black belt in 2012. In addition to owning a CrossFit gym and competing in the sport, Trey was a judge at the 2017 and 2018 CrossFit Games.

Trey felt blessed to have been Caylee’s father, Cherry’s partner, Penny and Whitney’s brother and to have met countless wonderful people through coaching, playing, working and volunteering.

Trey leaves his wife, Cherry, of Kihei, HI; his daughter, Caylee, of Kihei, HI; his brother, York Whitaker and his wife, Rose, of Bethesda, Maryland; his sister, Whitney Whitaker and her husband, Gerry Garfield, of Hebron; his sister, Penny Whitaker-Johnson and her husband, Dano Johnson, of Manchester; his nieces, Ellie Whitaker, and Nika Garfield and his beloved labrador, Abbey. Trey’s brother Chance Whitaker, passed in 1960.

There will be no visiting hours or remembrance service. Instead, after organ donation, Trey will be cremated and his ashes flung into the sea.

In lieu of flowers, please consider making a tribute gift to The Conservation Fund for Haleakala National Park.



Trey Whitaker

Former CrossFit gym owner, corporate manager, paratrooper, youth sports coach and jujitsu black belt. Now a trail steward at Haleakala National Park on Maui.