Honoring a Hero: The Life and Legacy of Captain Jason ‘Shady’ DeGroot, USN

As I reflect on the life of my friend Jason DeGroot, whom I’ve known since we were fresh Navy recruits, I am reminded of his impact on my life and the countless lives he touched with his loyalty, compassion, and humor.

Jason and I first crossed paths as roommates in Aircrew SAR school in Pensacola. Back then, we were two young men with ambitious dreams—mine to become a Navy SEAL, and Jason’s to soar the skies as a Naval Aviator. I think that’s what attracted us initially.

Soon into SAR school we figured out that he could iron precise military creases better than me, and I could shine boots better than him so our Sunday ritual before Monday uniform inspections was spent prepping over beers and guy talk in the barracks.

I still remember the black Kiwi shoe polish that smelled like painter thinner and candle wax and the spray starch Jason would use to hold a firm crease as he ironed out our uniforms with a sniper’s precision. Our room must have smelled like a densely packed New York dry cleaners.

After those formative days in Pensacola and basic A school, we were stationed in San Diego as young helicopter aircrew.

A few years later Jason went on to attend the United States Naval Academy, where he would had some trouble adjusting to boot camp life all over again. He told me the first year was the hardest then things started to get better.

I eventually got my orders to SEAL training with BUD/S class 215 and ended up visiting him his junior year at the Academy.

He would earn his Wings of Gold in 2001 when I was in Afghanistan with SEAL Team 3.

We always stayed in touch throughout our careers, and years later after I left the navy, Jason was there for me during one of the most challenging times of my life. My divorce.

He opened his home to me, offering not just a place to stay but a sanctuary where I could find friendship and support. During this time I witnessed firsthand the depth of Jason’s kindness and generosity.

We were both there for each other as we struggled to transition from the structured schedule of active duty to civilian life. Jason would end up staying in the reserves and flying for FEDEX while I became an entrepreneur.

Right when I was moving out of his place and getting on my feet he met Mia, the love of his life. It was if the universe had conspired to bring two souls together who were meant to be. Jason’s love for Mia and their children was boundless, and he was a devoted husband and father always.

He called me earlier this year to let me know about his stage four pancreatic cancer. I’m grateful for the two phone calls we had talking about our past antics and our current lives and families. He was positive and kept his fighting spirit to the very end. It was very humbling.

Captain Jason “Shady” DeGroot was a man of integrity, courage, and unwavering commitment to his country and his loved ones. His 25 years of exemplary service to the United States Navy were marked by countless achievements and the respect of all who served alongside him. Yet, it is his friendship, his kindness, and his unwavering support that I will remember most.

Jason, your legacy lives on in the hearts of those who knew and loved you. You were more than a friend; you were a brother. Your spirit will continue to inspire us, and your memory will forever be a source of strength and comfort to me.

Rest in peace brother. Until we meet again, know that you will always be remembered and deeply missed.

See you on the other side.

Brandon Webb

Honoring the Memory and Service of Captain Jason “Shady” DeGroot

Jason’s career was marked by numerous achievements and accolades.Upon completion of flight
training, he was selected to fly the S-3B Viking, serving in VS-21 based in Atsugi, Japan, in support
of Operation Iraqi Freedom. In 2005, he was hand-selected as anS-3B instructorpilot inVS-41.
Following the retirement of the S-3B, Jason transitioned to the C-2A Greyhoundin 2007. While
assigned to VRC-30,he served as a department head and training officer in support of both
Operation Enduring Freedom and Operation New Dawn. In 2010, Jason left active service and
joined VR-57 as a Selective Reserve Pilot flying theC-40A Clipper. Here, Jason was chosen as the
lead Instructor Pilot and NATOPS Officer. His dedicationto,and knowledge of the VR and VRC
communities led to his selection as the Commanding Officer of the newly formed VRM-30 and
VRM-50 Reserve Detachments flying the CMV-22B Osprey. His leadership and skill were evident
throughout multiple deployments and assignments. Jason’s commitment to excellence earned him
numerous awards, including the Meritorious Service Medal, the Air Medal with multiple
Strike/Flight awards, and several Navy Commendation Medals with Combat V.
Following his active Navy career, Jason continued to fly as a commercial airline pilot. After initially
flying for Southwest Airlines, he later joined FedExExpress, flying as a Memphis-based First Officer
on the Boeing 757 and 767.
Jason is survived by his beloved wife, Mia Sabatino DeGroot, whom he married on March 7, 2015;
their two children, Evangeline (age 8) and Harlan (age 6); and his mother, Vivian DeGroot. He will
be deeply missed by his family, friends, and all who knew him.

Naval Aviator’s Heaven

I hope there’s a place, way up in the sky,
Where Naval Aviators can go, when they have to die.
A place where a guy could buy a cold beer
For a friend and comrade whose memory is dear.
A place where no blackshoe or porkchop could tread,
Nor a Pentagon type would e’re be caught dead!
Just a quaint little O’club; kind of dark, full of smoke,
Where they like to sing loud, and love a good joke.
The kind of place, where a lady could go
And feel safe and protected by the men she would know.
There must be a place where old Navy pilots go
When their wings get too weary, and their airspeed gets low.
Where the whiskey is old and the women are young,
And songs about flying and dying are sung,
Where you’d see all the shipmates you’d served with before,
And they’d call out your name, as you came thru the door,
Who would buy you a drink, if your thirst should be bad
And relate to the others, “He was quite a good lad!”
And then thru the mist you’d spot an old guy
You had not seen in years, though he’d taught you to fly.
He’d nod his old head and grin ear to ear,

And say, “Welcome shipmate, I’m pleased that you’re here!
For this is the place where Naval Aviators come
When the battles are over, and the wars have been won.
They’ve come here at last to be safe and afar
From the government clerk and the management czar,
Politicians and lawyers, the feds and the noise,
Where all hours are happy, and these good old boys
Can relax with a cool one, and a well-deserved rest!
This is Heaven, my son, you’ve passed your last test!

—

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