Mothers Ancestors ♂

Perhaps the most famous relative on my mothers side of the family is Gracie O'Malley who married Donal O'Flaherty.  From her, I may have some of her feminist leanings.  My Grandfather Russel Bolen O'Flaherty's family came from Ireland.  Donal was Gracie O' Malley's first husband and they had 2 two sons as a result of that union.  There are numerous stories about Gracie O'Malley and here is one of them I found:

Grace O'Malley (also called Granuaile) was a famous pirate, seafarer, trader and chieftain in Ireland in the 1500's. She was born in 1530 in County Mayo, Ireland and was the daughter of sea captain Owen O'Malley. As a young child, Grace always knew she wanted to be a sailor but as a female, she was discouraged repeatedly. Female 
PirateExtremely upset when her father refused to take her on a sailing trip, legend has it Grace cut off all her hair and dressed in boys clothes to prove to her parents that she could handle the trip and live a seafarer's life. Seeing this, her father and brother laughed aloud and nicknamed her "Grainne Mhaol" meaning "Bald Grace" (which is believed to have led to her nickname "Granuaile.") Eventually, through her persistence, she was allowed to go to sea with her father and his fleet of ships.
As a child, Grace often sailed with her father on trading missions overseas. Once, upon returning from a trip to Spain, their ship was attacked by an English vessel. Grace had been instructed by her father to hide below deck if they ever were attacked, but she did not heed his advise. Instead she climbed up onto the sail rigging. Watching the battle from above, she noticed an English pirate sneaking up on her father, raising a dagger behind his back! The brave Granuaile leapt off of the rigging, through the air and onto the pirate's back.... screaming all the while! The distraction this caused was enough for the O'Malleys to regain control of the ship and defeat the English pirates.
She spent her young life learning the ways of the sea and grew to be quite the sailor--eventually having her own fleet of ships. Gold 
pieceHer family had become wealthy mainly through fishing and trade, but in her later life, Grace took up piracy by taking on Turkish and Spanish pirate ships and even the English fleets. She grew her estate to include a fleet of ships as well as several islands and castles on the west coast of Ireland.
In her later years, Grace developed her reputation as a fearless leader through her efforts in battle along side her followers. Legend has it that Grace gave birth to one of her sons while out to sea. The very next day following the birth of the baby, the ship was attacked by Turkish pirates. Though exhausted from giving birth Grace grabbed a gun, went on deck and proceded to rally her men against the Turks, forcing their retreat.
Grace married two times in her life. Her first husband was Donal O'Flaherty who was the son of the chieftain of the O'Flaherty clan and next in line for the post as chieftain. Grace and Donal married when was about 16 years old. In those times, it was common for families to arrange marriages so the union between Grace and Donal was probably more political than emotional at first. Pirate 
FlagThe O'Flahertys were a seafaring people, much like the O'Malleys, so Grace was right at home with their clan. Over the course of their marriage, Grace learned more about seafaring from Donal and his clan and added to her knowledge of sailing and trading at sea. Grace was soon in charge of the O'Flaherty fleet of ships and ruled the waters surrounding their lands. Although it was unusual for a woman to lead men, Grace earned the respect of all who followed her through her shrewdness as well as her knowledge of sailing and bravery at sea. Her husband, Donal, had a reputation for being quite a "hot head" and his temper eventually cost him his life in battle against a rival clan. They were married for a total of nineteen years.
According to Irish law, widows were entitled to a portion of their husbands estates. But for some reason, the O'Flahertys did not follow this tradition. Grace was forced to rely on the O'Flaherty clan for support. She did not like this, so she set out on her own, taking with her a loyal group of followers and traded on the seas to earn her own way. She used what she learned from her father in her youth and from her husband and eventually was able to break away from the O'Flaherty Clan altogether. Grace moved back with the O'Malley clan bringing her followers with her -- Grace had become a Chieftain in her own right and the heir as Chieftain of the O'Malley clan.
In equally as political a move, Grace married her second husband, Richard Burke in an effort to strengthen her hold on the west coast area of Ireland. Since the death of Donal, she had built her empire to include five castles and several islands in Clew Bay, but needed Rockfleet castle in the northeast side of the bay to complete her stronghold on the area.
Legend has it that Grace travelled to the Castle Rockfleet, knocked on the door and proposed marriage to Richard for a period of one year. She explained that the union would enable both clans to withstand the impending invasion by the English (who were slowly taking over the Irish lands around them.) It is believed that after exactly one year, Grace said to Richard, "I release you," apparantly offering him the option to end the marriage, but he must have really fallen for the lovely Granuaile, because they remained married until he died some seventeen years later.
Grace had a total of four children. Donal and Grace had three children, 2 boys and 1 girl. Their sons were Owen and Murrough and daughter Margaret. Later, when Grace married Richard, they had a son, Tibbot (or Theobald).
In 1593, after many difficult years fighting against the English and the capture of her brother and son by English forces, Queen 
ElizabethGrace visited Queen Elizabeth to make peace and ask for the release of her brother and son. Events leading up to the meeting between Grace and Queen Elizabeth had a significant impact on the meeting itself and Grace's behavior afterward.
Over Grace's lifetime, the English had taken over much of Ireland a peice at a time through a process called "Sumit and Regrant." The English would convince (or force) Clan leaders to submit their lands to the English and in return they were given an English title. Some Cheiftains surrendered, many rebelled-- Grace among the rebellious. She maintained her independence longer than most of the rest of Ireland, but in her later years, the pressure from English forces began to weigh heavily on her.
At 56 years old, Grace was captured by Sir Richard Bingham, a ruthless Governer appointed by the Queen to rule over the regranted territories. Soon after his appointment, Bingham sent guards to arrest Grace and have her hanged. Grace was apprehended and along with members of her clan, imprisoned and scheduled for execution. Determined to die with dignity, Grace held her head high as she awaited her execution. At the last minute, Grace's son-in-law offered himself as a hostage in exchange for the promise that Grace would never return to her rebellious ways. Bingham released Grace on this promise but was determined to keep her from power and make her suffer for her insurrection. Over the course of time, Bingham was responsible for taking away her cattle, forcing her into poverty, even plotting the murder of her eldest son, Owen.
During this period of Irish rebellion, the Spanish Armada was waging war against the English along the Irish and Scottish coastlines. It is not known whether Grace assisted the English against the Spanish or if she was merely protecting what little she had left-- but around 1588, Grace slaughtered hundreds of Spaniards on the ship of Don Pedro de Mendoza near the castle on Clare island. Even into her late 50's, Grace was fierce in battle.
In the early 1590's, Grace was still virtually pennyless thanks the constant efforts of Bingham to keep tight controls on her. There was a rather large rebellion brewing and Bingham feared that Grace would run to the aid of the rebels against the English. He wrote in a letter during this time that Grace was, "a notable traitoress and nurse to all rebellions in the province for 40 years."
Grace had written letters to the Queen demanding justice, but received no response. In 1593, her son Theobald and brother Donal-na-Piopa were arrested and thrown into prison. This was the final straw that prompted Grace to stop writing letters and go to London in person to request their release and ask for the Queen's help in regaining the lands and wealth that were rightfully hers.
Grace set sail and managed to avoid the English patrol boats that littered the seas between her homeland and London. The meeting took place in Greenwich Castle. The only record of this meeting that has survived are the lyrics to an old song that tell of Grace's presence in the court of the Queen:

No one really knows why Queen Elizabeth agreed to meet with Grace (let alone why she did not have her executed or imprisoned). Grace was fluent in Latin and thus was able to converse freely with the Queen. Grace explained that her actions in the past were not rebellion but rather acts of self-defense. She told of how her rightful inheritance from both husbands' deaths were wrongfully withheld from her and asked for them to be returned. She also asked for the release of her son and brother. In return for all of this, Grace agreed to use her strength and leadership to defend the Queen against her enemies by land and by sea.
The Queen agreed and Grace returned to Ireland and demanded Bingham release her son and brother and return her assets by order of the Queen. Bingham did release the two captives, but never did restore Grace her rightful possessions.
One interesting story is also worth noting. This allegedly occured during Grace's meeting with the Queen in England. It is said that during the meeting, Grace sneezed in the presence of the Queen and her lords and ladies. A member of the court, in an act of politeness, handed Grace an attractive and expensive lace handkerchief. She took the delicate cloth and proceded to blow her nose loudly then tossed the kerchief into a blazing fireplace. The members of the court were aghast that she would be so rude to toss an expensive gift so easily into the fire. The Queen then scolded her and said that the handkerchief was meant as a gift and should have been put into her pocket. Grace replied that the Irish would never put a soiled garment into their pocket and apparantly had a higher standard of cleanliness. After a period of uncomfortable silence, (during which the members of the court expected the Queen to have Grace executed for her rude behavior) nervous then roaring laughter followed. The Queen was amused. Cross
Granuaile was known as a fearless leader and fierce fighter. In her 70 years of life, she and her family saw the English rule spreading throughout Ireland, but through her strength and leadership saw that her clan and those around her were mostly unaffected by it. It is said that from the year of her death in 1603 and onward, that no Irish chieftain had been able to preserve the old Gaelic way of life as Granuaile and her family had done in her lifetime.
According to stories that my relatives have told me, I am a direct descendant of Grace O'Malley. But rather than simply accepting the stories as truth, I have begun the process of researching that branch of my family tree to obtain definitive proof, and would welcome comments from anyone else researching this family.

And from Wikipedia:

Marriage to O'Flaherty

Clare Island, associated with Grace O'Malley
Ní Mháille was married in 1546 to Dónal an-Chogaidh (Donal of the Battle) O'Flaherty, tánaiste or heir to the O'Flaherty title, which would have been a good political match for the daughter of the O'Mháille chieftain. As O'Flaherty tánaiste, Dónal an-Chogaidh one day expected to rule Iar Connacht, the area roughly equivalent to modern Conamara.[7]
She bore three children during her marriage to Dónal an-Chogaidh O'Flaherty:
  • Owen:[8] The eldest child and son, known to be extremely kind and forgiving. When Owen was in his late twenties, or early thirties, Richard Bingham tricked him and, as a result, Owen was murdered and Bingham and his troops took over Owen's castle.
  • Margaret:[8] Sometimes called 'Maeve', Margaret was much like Ní Mháille herself. She married and had several children. Ní Mháille and Margaret's husband[who?] were supposedly very close, and more than once Ní Mháille's son-in-law saved her from death.
  • Murrough:[8] Murrough was said to take after his father, Dónal, as he enjoyed warfare. He was also sexist, many times beating up his sister, Margaret, and refusing to listen to his mother because of her sex. Many sources report that Murrough, who seems to have had no sense of loyalty, betrayed his family and joined forces with Richard Bingham after the murder of Owen. When Ní Mháille heard of this, she swore she'd never speak to Murrough again for the rest of her life, though she would often insult him.
Later, the warring Dónal was killed in battle, and Ní Mháille recaptured a castle from the Joyces that had been his (now Hen's Castle in Lough Corrib). She afterwards returned to Mayo and took up residence at the family castle or tower-house on Clare Island.
After Dónal's death, Gráinne left Iar-Connacht and returned to O'Mháille territory, taking with her many O'Flaherty followers who were loyal to her.[9]
I found a Wikipedia source on The O'Flaherty Clan that sources Oscar Wilde as a O'Flaherty.

Oscar Wilde (16 October 1854 – 30 November 1900)

Wished to make it very clear that he was proud of his name, stating it in full as Oscar Fingal O'Flahertie Wills Wilde. Although in the UK Wilde's style causes him still to be taken for an Englishman, he only ever referred to himself as Irish or Celtic. Born in Dublin, he was educated at home until age nine, then at school in Enniskillen, punctuated with long holidays in counties Waterford, Wexford and Mayo (Grace O'Malley country) due to family relations there, and took classics at Trinity College, Dublin. He received a scholarship to go on to Magdalen College, Oxford, where he made a point of taking up several lines in the student register there by signing his name "Oscar Fingal Wills O'Flaherty Wilde”, perhaps an early indicator of the suppressed antagonism which would exist between him and the country which adopted him. His mother Jane Francesca Wilde (née Elgee, a.k.a. Speranza) was a successful writer and a poet for the revolutionary Young Irelanders in 1848 and a life-long Irish nationalist. Wilde's father, Sir William Wilde, was Ireland's leading Oto-Ophthalmologic (ear and eye) surgeon and was knighted in 1864 for his services to medicine - he also wrote books on Irish folklore and archaeology, such as "Lough Corrib, its Shores and Islands", first published in 1867, which included descriptions of O'Flaherty land and castles. Like many on both sides of the English / Irish divide at the end of the nineteenth century, Oscar Wilde was a strong supporter of Charles Stewart Parnell, a complex political proponent of Irish Home Rule, whose early death came shortly before Wilde's own. Following Wilde's imprisonment in Reading Gaol and rapid physical decline, in addition to complaining about “dying beyond my means” and insisting "either that wallpaper goes or I do", Wilde declared from his deathbed in France in 1900 that “if I were to outlive the century, it would be more than the English could stand."