When Samuel White's widow, Anne, died in 1880, she bequeathed the estate to her late husband's nephew, John Thomas, 6th Baron Massy. The Massys were a Protestant Ascendancy family who had come to Ireland in 1641 and owned extensive lands in Counties Limerick, Leitrim and Tipperary. Massy used Killakee House to entertain guests while shooting game on nearby Cruagh and Glendoo mountains. He also used the house to host parties during major events on the Dublin social calendar such as the Dublin Horse Show, the Punchestown Races and the Dublin Castle Season. During these events long lines of guests' carriages could be seen stretched along the road leading to the house. However, as a result of declining rental income and poor investment decisions, John Thomas Massy was in considerable debt when he died in 1915. By the time John Massy's grandson, Hugh Hamon Charles, 8th Baron Massy, inherited the estate, the family's finances were in an irreversible decline and in 1924 he was declared bankrupt and evicted from Killakee House. The Massys initially moved into the Stewards House before taking up residence in Beehive Cottage, the estate's gate lodge, by agreement with the bank. Hamon Massy, unable to find a job on account of his alcoholism became dependent on his wife, Margaret, whose modest salary from a job with the Irish Hospitals' Sweepstake was the family's only income. In the years up to his death in 1958, Hamon Massy, who became known as the "Penniless Peer", could be seen collecting firewood in the woods of his former family estate.