[5] He was active in GAA circles in early life, and refereed the 1914 All-Ireland Senior Football Championship Final.

He joined the IRB at the same time as his older brother Gerry in 1904,[6] following in the footsteps of his father, uncle and probably grandfather.

He was educated at the Synge Street CBS, but had a personality clash with one of the brothers so he refused to carry on his attendance at the school.

[8] In line with all the Sinn Féin MPs elected at that election, he did not represent his constituents at Westminster, but withdrew to sit in the declared independent Dáil Éireann (the First Dáil) and was named by Éamon de Valera as special envoy to the United States, a role his uncle Jack had played 25 years previously.

During the Irish War of Independence, Boland operated alongside Michael Collins, of whom he was a close friend.

In the ensuing Irish Civil War, he sided with the Anti-Treaty IRA which brought him into disagreement with his friend "Mick" Collins.

Six weeks later, on 31 July, Boland was shot by soldiers of the National Army when they attempted to arrest him at the Skerries Grand Hotel.

[13] Two officers entered his room and Boland, who was unarmed, was shot and mortally wounded during a struggle:[14] Reports of how and why he was shot vary and it is hard to establish an accurate historical reason, given the highly partisan views of the parties involved in the civil war conflict of brothers.