After almost twenty years of cricket with Middlesex, O’Brien retired to flit between his homes in Dublin, Cork and London. He had married Gundrede, daughter of Sir Humphrey de Trafford, and she bore him ten children – the more incredible that he never wore that vital piece of a cricketer’s protection, the “box”.
He got involved in Irish cricket, and captained the team on its inaugural first-class tour in 1902, scoring 167 against Oxford University which was the Ireland record until 1973. He continued to play well into his 50s, and in 1914 was selected for a final big fixture in England. Aged 53, he scored 90 and 111 in his final first-class match.
Enjoying the life of the country squire in Lohort Castle, near Fermoy, O’Brien became involved in equestrian affairs. But after he bought a lame horse from a neighbour, Alexis Burke-Roche, he was embroiled in a ruinous litigation.
He met Burke-Roche out hunting and accused him of fraud – ‘You are a liar and a cheat and a swindler; you have lived by swindling for the past 20 years’ – which provoked a writ for slander. O’Brien tried to nobble the jury, which led to the collapse of the case and a retrial.
O’Brien lost that, and had to pay £5 in damages, a fine for the jury-tampering, and all the costs, which almost ruined him.
He then got involved in politics and was an ardent Home Ruler, helping John Redmond to drill recruits to the Irish Volunteers. On the outbreak of the First World War he helped in recruiting for the British Army, and at the age of 54 joined the Derbyshire Remounts.
His son, Timothy junior, joined the Royal Field Artillery and was killed in Delville Wood on the Somme in 1916, and there were more tragedies, as several of his offspring died in childhood. His daughter Sicile was an early aviator and the second woman in Britain to hold a commercial licence. She lost a leg in a plane crash in 1928, and her life in another three years later.
O’Brien lived quietly thereafter, but lost his beloved Lohort Castle to IRA arsonists during the War of Independence. He lived in Rochford Manor in Dublin for a time, and later lodged in an apartment in the National Yacht Club in Dun Laoghaire.
He became embroiled in another minor scandal in 1938, when ten patients at Mullingar Mental Hospital were refused permission to travel to watch the Ireland v Australia cricket game at College Park, Dublin.
One politician on the management committee said: “We are long enough aping the foreigner; let us encourage our own native pastimes.” Another objector suggested that patients be sent to watch Gaelic matches in Longford, or to a 1798 celebration at Ballinamuck. His proposal was passed unanimously.
An Irish Times reporter sought the views of Sir Timothy, then aged 76.
“I never considered it as a foreign game”, he said. “I played it and there is no doubt that it is the best game. Of course, I don’t mean that cricket they play at The Oval; that is a dreadful game. It just bores you stiff.” O’Brien was probably referring to a one-sided test match a week earlier when England made 903-7 to beat Australia by an innings and 579 runs.
“As to the game not being encouraged in Ireland – well, the climate is against … and cricket grounds are expensive things and they are not too well off in Ireland.
“But not to encourage cricket because it is a foreign game? Ah well, there are a lot of fools going about in Ireland as in England.”
O’Brien lived on in the Isle of Man until 1948, and was the oldest test cricketer at the time of his death, aged 85.