Was the fist 35/94 E to enter Iraq during the first land assault in Operation Iraqi Freedom March 20 2003. He was attached to the 1/30th Infantry as an armed escort to fuelers and traveled through the battle field 15 miles with his most trusted soldier Steven Drakes. He assisted the 1/30 Infantry in securing the fist combat objective and also cleared 2 multi-level structures finding maps,enemy communications and a underground weapons cashe. He found this by falling through a trap door. SGT Taylor modified his FM communication platform and relayed battle instructions to distant units as far as 65 kms away.He and Steven Drakes were recommended for a ARCOM with valor,but never recieved it. SGT Chester Taylor was credited for securing the airfield and traing over 400 Soldiers and Officers in using FM communications and Navigation systems. He also deployed to OIF 3,and 5 as the Communications Sergeant for B 203rd FSB/BSB. He was well respected and regarded as the best in his profession.