By 1920 the War of Independence was in full swing and Barry was involved in many skirmishes with Company C. By this time he was a Section Commander. On June 1st, 1920, Company C in a daring escapade, under the command of Peadar Clancy, attacked King’s Inn and captured a large quantity of ammunitions and weapons. In another incident, Barry himself led a group which captured the guardroom on Constitution Hill. More than 25 British soldiers were seized in the raid but released unharmed.
On September 20th the Volunteers ambushed an army bread van on Queens Street near Monks Bakery. In the ensuing gun battle a young British soldier was fatally wounded. The Volunteers fled the scene when British reinforcements arrived. They escaped except Barry who was captured while hiding under a lorry. It is believed Barry’s pistol jammed in the attack. Certainly, there is no evidence that he fired any of the fatal shots.
He was interrogated and tortured by the authorities but steadfastly refused to reveal the identities of his accomplices. As a result he was court-martialed and sentenced to death on October 20th.
Several unsuccessful rescue attempts were made in the following days. Meanwhile, on October 25th the Lord Mayor of Cork, Terence MacSwiney died from hunger strike generating huge world-wide publicity. He was buried in Cork on October 29th. Most observers believed that the authorities would not go ahead and execute Barry in the midst of a tense political situation.
The night before his execution, Barry’s mother came to her condemned son’s cell on a last visit. During a long awkward moment of grief stricken silence, when no one knew what to say, Kevin began to sing softly an old marching song: