O’Riordan joins the Communist Party of Ireland in 1935 while still in the IRA and works on the communist newspaper The Irish Workers’ Voice. In 1937, following the urgings of Peadar O’Donnell, several hundred Irishmen, mostly IRA or ex-IRA men, go to fight for the Spanish Republic in the Spanish Civil War with the XVth International Brigade. They are motivated in part by enmity towards the 800 or so Blueshirts, led by Eoin O’Duffy who go to Spain to fight on the “nationalist” side in the Irish Brigade. He accompanies a party led by Frank Ryan. In the Republic’s final offensive of July 25, 1938, he carries the flag of Catalonia across the River Ebro. On August 1, he is severely injured by shrapnel on the Ebro front. He is repatriated to Ireland the following month, after the International Brigades are disbanded.
In 1938 O’Riordan is offered an Irish Army commission by the Irish Free State but chooses instead to train IRA units in Cork. As a result of his IRA activities during World War II, or the Emergency as it is known in neutral Ireland, he is interned in the Curragh internment camp from 1939 until 1943 where he is Officer Commanding of the Cork Hut and partakes in Máirtín Ó Cadhain’s Gaelic League classes as well as publishing Splannc (Irish for “Spark,” named after Vladimir Lenin‘s newspaper).
In 1944 O’Riordan is founding secretary of the Liam Mellows Branch of the Labour Party and in 1945 is a founding secretary of the Cork Socialist Party, whose other notable members include Derry Kelleher, Kevin Neville and Máire Keohane-Sheehan.
In all O’Riordan runs for election five times, campaigning throughout for the establishment of a socialist republic in Ireland but given Ireland’s Catholic conservatism and fear of communism, he does so without success. He does, however, receive playwright Sean O’Casey‘s endorsement in 1951.
O’Riordan’s participation in the Spanish Civil War is always an important part of his political identity. In 1966 he attends the International Brigades’ Reunion in Berlin and is instrumental in having Frank Ryan’s remains repatriated from Germany to Ireland in 1979.
O’Riordan is a member of the Irish Chile Solidarity Committee and attends the 1st Party Congress of the Communist Party of Cuba in 1984. He also campaigns on behalf of the Birmingham Six and attends their Appeal trial in 1990. He serves as General Secretary of the Communist Party of Ireland (1970–83) and as National Chairman of the party (1983–88). He publishes many articles under the auspices of the CPI.
O’Riordan’s last major public outing comes in 2005 at the re-dedication of the memorial outside Dublin’s Liberty Hall to the Irish veterans of the Spanish Civil War. He and other veterans are received by President of IrelandMary McAleese. He is also presented with Cuba’s Medal of Friendship by the Cuban Consul Teresita Trujillo to Ireland on behalf of Cuban President Fidel Castro.
In 1969, according to Soviet dissident Vasili Mitrokhin, O’Riordan is approached by IRA leaders Cathal Goulding and Seamus Costello with a view to obtaining guns from the Soviet KGB to defend Irish republican areas of Belfast during the communal violence that marks the outbreak of the Troubles. Mitrokhin alleges that O’Riordan then contacts the Kremlin, but the consignment of arms does not reach Ireland until 1972. The operation is known as Operation Splash. The IRA splits in the meantime between the Provisional IRA and the Official IRA and it is the latter faction who receives the Soviet arms. Mitrokhin’s allegations are repeated in Boris Yeltsin‘s autobiography.
O’Riordan’s book, Connolly Column – The Story of the Irishmen who fought for the Spanish Republic 1936–1939, is published in 1979 and deals with the Irish volunteers of the International Brigade who fought in support of the Spanish Republic against Francisco Franco in the Spanish Civil War (1936–1939). An updated version of the book is reprinted in 2005 and is launched by the Lord Mayor of Dublin, Cllr. Michael Conaghan at a book launch at SIPTU headquarters, Liberty Hall. The book is the inspiration for Irish singer-songwriter Christy Moore‘s famous song “Viva la Quinta Brigada.”
In 1991, O’Riordan’s wife dies at the age of 81 at their home. He continues to live in their family home before moving to Glasnevin in 2000 to be close to his son Manus who lives nearby. He lives there until falling ill in November 2005 and is taken to the Mater Hospital. His health rapidly deteriorates and he quickly develops Alzheimer’s disease. Soon afterwards he is moved to St. Mary’s Hospital in the Phoenix Park where he spends the final few months of his life, before his death at the age of 88 on May 18, 2006.
O’Riordan’s funeral at Glasnevin Crematorium is attended by over a thousand mourners. Following a wake the previous night at Finglas Road, hundreds turn up outside the house of his son Manus and traffic grounds to a halt as family, friends and comrades – many of whom are waving the red flag of the Communist Party of Ireland – escort O’Riordan to Glasnevin Cemetery. A secular ceremony takes place led by Manus O’Riordan, Head of Research at SIPTU, with contributions from O’Riordan’s family, Communist Party general secretary Eugene McCartan and IBMT representative Pauline Frasier.
Gregory becomes involved in republican politics, joining Sinn Féin and the Irish Republican Army (IRA) in 1964. In UCD he helps found the UCD Republican Club, despite pressure from college authorities, and becomes involved with the Dublin Housing Action Committee. Within the party he is a supporter of Wicklow Republican Seamus Costello. Costello, who is a member of Wicklow County Council, emphasises involvement in local politics and is an opponent of abstentionism. Gregory sides with the Officials in the 1970 split within Sinn Féin. Despite having a promising future within the party, he resigns in 1972 citing frustration with ideological infighting in the party. Later, Costello, who had been expelled by Official Sinn Féin, approaches him and asks him to join his new party, the Irish Republican Socialist Party. He leaves the party after Costello’s assassination in 1977. He is briefly associated with the Socialist Labour Party.
Although Gregory is reviled in certain quarters for effectively holding a government to ransom, his uncompromising commitment to the poor is widely admired. Fianna Fáil loses power at the November 1982 general election, and many of the promises made in the Gregory Deal are not implemented by the incoming Fine Gael–Labour Party coalition.
Gregory is involved in the 1980s in tackling Dublin’s growing drug problem. Heroin had largely been introduced to Dublin by the Dunne criminal group, based in Crumlin, in the late 1970s. In 1982 a report reveals that 10% of 15- to 24-year-olds have used heroin at least once in the north inner city. The spread of heroin use also leads to a sharp increase in petty crime. He confronts the government’s handling of the problem as well as senior Gardaí, for what he sees as their inadequate response to the problem. He co-ordinates with the Concerned Parents Against Drugs group in 1986, who protest and highlight the activities of local drug dealers, and defend the group against accusations by government Ministers Michael Noonan and Barry Desmond that it is a front for the Provisional IRA. He believes that the solution to the problem is multi-faceted and works on a number of policy level efforts across policing, service co-ordination and rehabilitation of addicts. In 1995 in an article in The Irish Times, he proposes what would later become the Criminal Assets Bureau, which is set up in 1996, catalysed by the death of journalistVeronica Guerin. His role in its development is later acknowledged by then Minister for JusticeNora Owen.
Gregory also advocates for Dublin’s street traders. After attending a sit-down protest with Sinn Féin Councillor Christy Burke, and future Labour Party TD Joe Costello on Dublin’s O’Connell Street in defence of a street trader, he, Burke and four others are arrested and charged with obstruction and threatening behaviour. He spends two weeks in Mountjoy Prison after refusing to sign a bond to keep the peace.
Gregory remains a TD from 1982 and, although he never holds a government position, remains one of the country’s most recognised Dáil deputies. He always refuses to wear a tie in the Dáil chamber stating that many of his constituents could not afford them.
Gregory dies on January 2, 2009, following a long battle with cancer. Following his death, tributes pour in from politicians from every party, recognising his contribution to Dublin’s north inner city. During his funeral, politicians from the Labour Party, Fianna Fáil and Fine Gael are told that although they speak highly of Gregory following his death, during his time in the Dáil he had been excluded by many of them and that they were not to use his funeral as a “photo opportunity.” He is buried on January 7, with the Socialist Party‘s Joe Higgins delivering the graveside oration.