Early in 1919, Tobin had become Collins' chief executive in the Intelligence Directorate handling the many spies in Dublin Castle, including double agent David Neligan.
[2] Tobin was involved in planning the assassinations of British soldiers, informants, members of the Royal Irish Constabulary, the Dublin Metropolitan Police, and operatives of MI5.
He constructed detailed profiles of everyone remotely connected to the British government, often using Who's Who, The Morning Post, and The Times – a newspaper that described him as "one of the most formidable of [the] Twelve Apostles".
[3] Collins' intelligence operations were based at 3 Crow Street, Dublin, where Tobin had the assistance of Tom Cullen and Frank Thornton.
Tim Pat Coogan and James Mackay have examined Tobin's involvement in the assassination of British Field Marshal Sir Henry Wilson.
[4] Following the Anglo-Irish Treaty, he was appointed deputy director of intelligence in the new state and assigned to the Criminal Investigation Department based at Oriel House.
Tobin was placed on the Army Council and was Director of Intelligence from September 1922 until his appointment as Senior Aide-de-Camp to the new Governor General, Tim Healy in November 1922.
[3] In October 1922, Tobin's brother Nicholas, a Free State captain, was accidentally shot dead by his own troops during the raid and capture of a bomb making factory at number 8 Gardiner's Place, Dublin.
Disillusioned with the continuing hostilities and in the aftermath of the death of General Collins he formed an association called the IRA Organisation (IRAO) or "Old Irish Republican Army" to distinguish themselves from the anti-treaty insurgents.
[9] In later years, Tobin would rebuild relations with his Civil War foes and joined De Valera's Anti-Treaty Fianna Fáil Party.