On May 22, 2009, Caldwell was off-duty, driving behind a patrol car from the Allen Park Police Department when he heard repetitive shotgun blasts.  The Allen Park officer turned his patrol car around and drove in the direction of the gunfire; Caldwell followed.

Immediately after turning onto a residential street, multiple shots were fired at the Allen Park patrol car from one of the homes, severely wounding the Allen Park officer.  Risking his own safety, Caldwell left his vehicle to move the wounded officer to a safe position.  He then utilized first aid techniques to treat him until another officer arrived to transport him to the hospital.

During this time, the gunman was still barricaded in his residence, firing into the surrounding neighborhood.  Fearing the gunman would exit the home and harm an innocent bystander, Caldwell commandeered the wounded officer's rifle and moved closer to the house, where he would be able to intercept the gunman should he emerge.   

Additional officers and an emergency response team arrived, eventually resolving the situation after three hours.  During this time, the gunman fired over 200 rounds, some hitting only feet away from Caldwell's position.

Upon reviewing this incident, the MSP Board of Awards recognized Caldwell's heroic actions and willingness to ignore his own personal safety and well-being to rescue and provide aid to an officer unknown to him.

Caldwell enlisted with the department in 1998, graduating as a member of the 117th Trooper Recruit School.  After graduation he was assigned to the Jackson Post.