Leaders of the Pack: 104th Training Division (LT) 2020 Best Warrior Competition winners


Drill Sergeant of the Year (Center) 1-398th Command Sgt. Maj. Renfrow (left) and DS Osborne (right) surrounded by other 1-398th competitors DS McDowell, Sgt. Sack on the left and DS Webb and DS Masterson on the right.

The 104th Division (LT) Best Warrior Competition (BWC) took place this year at Fort Knox, KY from March 5-7. The following competitors won the title of Soldier of the Year (SOY), NCO of the Year (NSOY) or Drill Sergeant of the Year (DSOY) for their respective brigades:

“I learned [the NCO creed] and lived it during my career so far, it’s been a guiding light when darkness was present.”— Staff Sgt. Derrick Osborne

Spc. Joseph Dempsey with Bravo Company, 2nd Battalion, 319th Regiment (Cadet Summer Training) was named 1st Brigade’s SOY. He is from Roanoke, Virginia, and currently serves in the Salem, Virginia, unit as a trainer. He enlisted in 2016 “…because I wanted to fight Isis…I was reading an article about their slave camps for adolescent kids. That’s all it took to get me to join.” Dempsey is also air assault qualified and previously served in the 1-32 Cavalry, 1st Brigade Combat Team, 101st Airborne Division. He is currently pursuing a degree in Criminal Justice and would like to serve in law enforcement after graduation.

NCO of the Year Sgt. Rehn (left) and CSM Kaim (right).


Spc. Kevin Caladie with Alpha Company, 3rd Battalion, 304th Regiment (USMA), was named SOY for 2nd Brigade. He is from New Brunswick, New Jersey and currently serves in the Saco, Maine, unit training West Point cadets on the AT-4. He joined the military because of family members who have served, “Service to country is a staple in the Caladie family. My ‘Pop-pop’ and great uncle were Vietnam veterans with the USMC.” When asked what his advice would be to Soldiers who are considering next year’s BWC, Caladie stated “never quit”. Spc. Caladie has completed Basic Leader Course, and is currently studying Business Management with a long term goal of a degree in real estate law.

NCO of the Year CSM Phipps, Sgt. Sack and 2nd Brigade Command Sgt. Maj. Neil Pierce.


Sgt. Jarrick Rehn with Alpha Company, 3rd Battlion, 414 Regiment (Cadet Summer Training) was named 1st Brigade’s NSOY. He is from Tacoma, Washington, and currently serves on Joint Base Lewis-McChord as a trainer. He enlisted in 2009 for pure love of country. “I’ve always wanted to serve” he stated. He started his military career at Alpha Company, 2nd Battalion, 7th Calvary, 4th Brigade Combat Team, 1st Cavalry Division, Fort Hood, Texas. An Infantryman, he deployed to Iraq as an automatic rifleman and grenadier for two campaigns; Operation Iraqi Freedom and Operation New Dawn achieving many decorations and awards throughout his career. Before arriving at the 3-414th REGT (CST), he also served as a rifle team leader in the 1st Battalion, 27th Infantry Regiment, 2nd Brigade Combat Team, 25th Infantry Division in Hawaii and as a grenadier in the 2nd Battalion, 506th Infantry Regiment, 4th Brigade Combat Team, 101st Airborne Division (Air Assault) at Fort Campbell, KY. When asked what kept him resilient during the challenging times in the competition, Rehn replied, “Just knowing I had to win. I grew up being very competitive and couldn’t quit at anything and always had to try.” In his free time, Rehn enjoys rock climbing, bouldering, running and taking his family and dogs to the park.

Spc. Joseph Dempsey


Sgt. Rickey Sack Jr., with Headquarters, 1st Battalion, 398th Regiment (BCT) was named 2ND Brigade NSOY. He is from Lynnville, Indiana, and currently serves in the Owensboro, Kentucky unit as a S3 Operations Sgt. Sack enlisted in 2008, has completed Basic and Advanced Leader courses, and deployed during Operation Enduring Freedom in 2011-12, receiving a number of awards that included the Army Commendation Medal. When asked what competing in the BWC means to him he stated, “It enables me to push myself and to use the knowledge that I have gained throughout my military service as well as learning things I have yet to learn in my time I have been in the military.” In his free time, he enjoys hunting and camping, exercising and studying. Sack is also a volunteer firefighter and is pursuing a Bachelor’s degree to become a mental health counselor.

Spc. Kevin Caladie


Staff Sgt. Derrick Osborne with Charlie Company, 1st Battalion, 398th Regiment (BCT) was named 2nd Brigade DSOY. He is from Calhoun, Kentucky, and currently serves in the Evansville, Indiana, unit as the Senior Drill Sergeant responsible for the training and successful development of drill sergeant candidates. Drill Sergeant Osborne has completed numerous professional military schools, is instructor and Cavalry Scout qualified, and has served in this role the past six years of his eleven years in the military. He credits his wife who also serves for his reason for joining the service and counts his Command Sgt. Maj. CSM Renfrow along with his wife as mentors stating “Without them I would not be where I am at and the NCO I strive to be.” He also considers the NCO creed as an important, early resource, “I learned [it] and lived it during my career so far, it’s been a guiding light when darkness was present.” Although he admits long competition days and nights wore him down, he utilized the camaraderie and support from other Soldiers from his battalion who were also there competing to stay motivated. When asked what he would advise Soldiers who are considering the competition, he stated “Care about what you’re doing. Strive to be who you want your Soldiers to be.”

Soldier of the Year From right to left, 1st Brigade Command Sgt. Maj. Todd Kaim, 104th Division (LT) Command Sgt. Maj. William Phipps,Spc. Dempsey and Spc. Caladie.


The winners will now go on to compete in the 108th Training Command BWC during the summer.


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