Tough Ruck 2025 – Walking 26.2 Miles for Those Who Can’t
Every spring, I lace up my boots, throw on a 20-pound ruck, and step off for 26.2 miles in honor of our fallen heroes and the families they left behind.
This year will be my 10th consecutive Tough Ruck — and it will be Oliver’s 3rd marathon right by my side.
For those who don’t know, Tough Ruck raises money to support Gold Star families, and every mile we carry those names on our rucks is a reminder of the cost of freedom and the people who continue to live with that loss every single day.
I’m asking for your support again — not for me, but for them.
⭐ I will match every donation, dollar for dollar.
Whatever you choose to give, I’ll double it.
And this year, I’m paying it forward even further. For the next month until 13 Jan 2026, all matched donations will be given to two organizations that have made a direct impact on my life and the veteran community:
🐾 22 Mohawks – Pups for Vets Program
They’re the organization that gifted me Oliver, my service animal, and gave me back more peace and stability than I can ever repay.
🚁 Military Helicopter Air Crew Veterans
A community that supports those who served as helicopter crew members. These are my people — my brothers and sisters from the aircraft I once flew in, still supporting each other long after the uniform comes off.
Why I do this.
Because service doesn’t end when the enlistment contracts do.
Because the families of the fallen deserve to know their loved ones are never forgotten.
Because organizations like 22 Mohawks and the Military Helicopter Air Crew Veterans community are changing lives — mine included.
And because if we don’t take care of each other, no one else will.
If you’re able to donate, even a little, it truly makes a difference.
And if you can’t, a simple share helps more than you know.
Support Tough Ruck:
👉 www.toughruck.org
Thank you for standing with me, with Oliver, and with the families we ruck for.
– James & Oliver
“Never above you, never below you… always beside you.”
I AM TOUGH RUCKING FOR AMERICA'S FALLEN MILITARY & FIRST RESPONDERS
This April, I will be joining Tough Ruck Nation to complete a marathon with a weighted rucksack (backpack). Tough Ruck 26.2 Boston is an elite group of 1000 who ruck to HONOR AMERICA'S FALLEN MILITARY & FIRST RESPONDERS. We humbly carry the names of the Fallen on our rucks as they will NEVER BEEN FORGOTTEN. We will also be raising critical funds for our Warriors. This is where we need your help! The essential ideal that drives our efforts is simple: as much as our Warriors have sacrificed, they and their families deserve the best care and support available in their hour of need. Your tax-deductible donation provides a lifeline to a Warrior.
This year will be my TENTH consecutive marathon and Oliver's second. We do it to honor those who have given their lives so that we may enjoy the freedom of our great country. I cannot express the feeling of being awarded the medal by Gold Star parents.
We greatly appreciate your support.
Semper,
Gunny and Sr "Oliver" Chesty
On April 15, 2013, Tough Ruckers were at the finish line of the Boston Marathon and joined the first responders to help those that were injured by the horrific blasts. They truly exemplify the best of what our Nation is. Today the Tough Ruck takes place the weekend before Boston Marathon Monday. Tough Ruck is the only ruck march partnered with the Boston Marathon and finishers are awarded the official Boston Marathon Medals and receive recognition from the Boston Athletic Association. Military Friends Foundation is the official charity of Tough Ruck Nation.
