Career
Besides the case of his accession above, O'Donovan is first noted in 1586 for burning to the ground the newly built house of the Protestant Bishop of Cork, Cloyne and Ross, William Lyon. Not only was the new house rather ostentatious, but Lyon was also accused of stealing and selling priceless gold and silver artifacts from the early period of the church. It is possible, however, that O'Donovan was guilty of burning the whole town of Ross or Rosscarbery itself, and his men may have slain one of Lyon's daughters in the attack. According to Lyon himself in 1615 nearly thirty years after the incident:
My house was burned by one Donovan, a neighbour in wild rebellion. He destroyed the glass windows of the church, took the lead off, pulled down the Queen's arms then standing over the gate of my house and trod them under-foot.
Although not among the major figures of his time, Donal II was in their company and active in Munster affairs during the Nine Years' War, being one of the few southern lords to support Hugh O'Neill. In March 1599 pledges of loyalty to the English Crown were received from all the lords in Carbery except for O'Donovan and some MacCarthys, and because of this Sir Thomas Norris "... caused their castles and houses to be taken and razed, and their people and lands to be spoiled", as he wrote to the Privy Council. But a year later O'Neill was both widely regarded and acting as virtual King of Ireland, or much of it, and was acknowledged by his supporters in Munster as such, including O'Donovan, wisely because those who refused had their lands wasted. In late 1599 Donal joined Florence MacCarthy, whom O'Neill was acknowledging the MacCarthy Mór and King of Desmond, and Owen Mac Egan in O'Neill's camp at Inniscarra near Cork city, in writing an appeal to Donogh Moyle MacCarthy, one of Owen MacCarthy Reagh's sons and thus O'Donovan's brother-in-law, to join them. The letter was intercepted, and for his part and signature Donal's people were "pacified" savagely by the English forces under the command of Captain George Flower, who related:
From Ross we marched over the Leape, into O Donovan's country, where we burned all those parts, and had the killing of many of their churls and poor people, leaving not thereon one grain of corn within ten miles of our way, wherever we marched, and took a prey of 500 cows which I took to be drowned and killed, for that we could not trouble ourselves to drive them in that journey.
The plan was that O'Donovan and Florence's brother, Dermod Maol MacCarthy, would invade a number of territories to the north of Carbery, but this was obviously unrealized. In any event, not long after, when Philip III of Spain sent his forces to Munster, 100 men out of the 700 were assigned to Donal's command, fully equipped and paid for, to supplement his own forces. According to Philip O'Sullivan Beare, he was one of the principal men of the relief army led by Donal Cam O'Sullivan Beare (slayer of his brother Diarmaid) to support Pedro de Zubiaur at Castlehaven in early December 1601, which led to what was according to O'Sullivan Beare a small but spectacular victory for the Spaniards and Irish:
At their arrival the English were daunted and remained in their ships, and Zubiaur, elated and emboldened, took his cannon from the vessels and for two days right vigorously bombarded the English fleet...
However the English also claimed victory and moderns scholars are very divided on who should be considered the winners. Two months later, an apparently poorly informed or otherwise motivated Sir George Carew wrote to the English government on 15 February 1602:
... Few of the 'provincials' here were in rebellion. The best of them, namely Sir Fynin O'Driscoll, O'Donovan and Sir Owen McCartie's sons, have not joined Tyrrell and the northern rebels, and ask to be received to mercy. They say they only conversed with Tyrone, O'Donnell and the Spaniards, and did no harm to any of her Majesty's subjects. I believe this is true.
But this was only true in the sense that they were not all present at the final Battle of Kinsale itself in late December/early January, almost a month after Castlehaven, although apparently O'Donovan made an appearance (on the Irish side) earlier during the siege. Changing allegiance after this ruinous event, O'Donovan joined Owen's sons Finghin and Donogh Maol, and O'Driscoll, in siding with the English, and O'Sullivan Beare wasted the territory of Clancahill after hearing of it.
A surprising event occurred shortly after when some of O'Donovan's men, under the command of Finghin, killed Dermod Maol MacCarthy (cousin of O'Donovan) who was engaged in a cattle-raid into O'Donovan's territory. Dermod Maol was regarded as the chief threat after Florence to the English in Munster (now along with O'Sullivan Beare, who joined the cause late) He and O'Sullivan Beare had been joined in continuing against the English by Cornelius O'Driscoll, son of Sir Fineen who was now opposing them. After a period Finghin and Donogh Maol MacCarthy may have gone back to the rebel side but O'Donovan remained loyal to the English, even though his sept was divided in their allegiances.
In July 1606, Donell M'Carthy, the M'Carthy Riough, petitioned the Earl of Salisbury that Donell O'Donevan, for whose loyalty petitioner's son was made surety and suffered four and a half years of imprisonment during the recent wars, should pay damages to him. Prior to the fall of the Gaelic order, it was common that pledges were secured by the holding of the offspring of those making the pledge, or in this case, those guarantying the conduct of those under them.
