[1] He was educated at Scoil Íosagáin and Coláiste Chaoimhín in Crumlin (both run by the Christian Brothers) and at University College Dublin (UCD).

The proposal required seven Sinn Féin MPs in northern Irish border constituencies to resign in favour of a pact between the four largest anti-Brexit parties in Ireland, thereby triggering by-elections at a certain date in mid-September.

O’Toole believed they would result in a more hardline anti-Brexit parliamentary faction that would make a stronger case for a no-confidence vote in Johnson.

[13][non-primary source needed] The proposal was sharply criticised by Sinn Féin leader Mary Lou McDonald, who claimed the existing anti-Brexit factions in Parliament were strong enough without the party making too many policy concessions.

[14][non-primary source needed] A 26 June 2018 column in The Irish Times by O'Toole examined how the Donald Trump administration's policies and public-facing communications about immigration and asylum-seekers from Mexico might be deliberately calculated to bring elements of fascism to the U.S.[15][non-primary source needed] An April 2020 column in The Irish Times asserted that Trump's destruction of the public image and reputation of the United States culminated with his bungling of the COVID-19 pandemic crisis,[16][non-primary source needed] and that subsequently pity was the only appropriate feeling for the American people, the majority of whom had not voted for him.

In a 2024 New York Review of Books essay, O'Toole rejects the common interpretation of William Shakespeare's tragedies in terms of protagonists' flaws leading to their own destruction.

It is a fairground wall of death in which the characters are being pushed outward by the centrifugal force of the action but held in place by the friction of the language.

We return to the tragedies not in search of behavioral education but because the wilder the terror Shakespeare unleashes, the deeper is the pity and the greater the wonder that, even in the howling tempest, we can still hear the voices of broken individuals so amazingly articulated.