Dan Breen was an integral and powerful man in Ireland’s long fight for independence. He was a husband and father, a gangster, a politician, a speakeasy operator, and an author, but first and foremost he was a self-described soldier who was dedicated to freedom.

It was Breen, together with seven other men, who kicked off the War of Independence in Ireland. Their mission became known as the Soloheadbeg Ambush and it resulted in the deaths of two Royal Irish Constabulary men. This ambush is widely considered to be the start of the war. Breen rose quickly through the ranks of the Irish Republican Army garnering a reputation for being bold, ruthless, and brave. He orchestrated jailbreaks, assassinations and ambushes and was wounded in action several times. The price on his head reached £10,000 at one point and he was considered the most wanted man in Ireland but this did not stop him from fighting every chance he could.

When the Anglo-Irish Treaty was introduced to bring the War of Independence to an end, Dan Breen denounced it completely, saying “I would never have handled a gun or fired a shot… to obtain this Treaty.” The very premise of the agreement infuriated him and he considered anyone who supported the treaty to be enemies and traitors, even if they had been comrades in arms before. He continuously attacked Free-State forces and who they actually were never mattered to him. Strangely, this didn’t stop politicians on both sides of the treaty debate from choosing Breen as their candidate in the elections of June 1922. In the end he was not elected, and he just kept on fighting. Ironically it was the Irish forces who finally arrested him, not the English. He was released a few months into his sentence after both a hunger and a thirst strike. In 1924 he wrote a hugely popular memoir called “My Fight for Irish Freedom.”

Just a few years after the book was published, a jaded and disappointed Breen packed up and went to America, where he operated an illegal speakeasy and tried to rent himself out as a tough guy and hired gun. He was a hard, macho man who picked up a gangster persona in the years he was in the United States that he never fully lost, even when he returned to Ireland a few years later. When he moved back home he started a life in politics, representing Tipperary as a Fianna Fail politician. He held his seat for more than thirty years, despite his controversial opinions, deep resentment, and violent past.

As a politician Breen met several world leaders including Mahatma Gandhi, whose peaceful resistance did not sway the Irishman away from advocating for violent uprising in the region. He also supported Nazi Germany (like many other members of Fianna Fail) and even sent Hitler a congratulatory note about his rise to power. His support was a little more significant and open than many others – he kept a photo of “the Fuhrer” in his home and attended funerals of prominent Nazi leaders and spies. He seemed to be quite fond of people and movements that displayed the same brutish force he had used for so many years as a fighter.

Soon his focus returned to Ireland. He battled extensively for a military pension but he did not care for the process of getting one. Breen hated being questioned and was incredibly hostile when he was asked for proof of his service.  When they finally did issue his pension Breen continued to argue, saying the amount they paid a special soldier like himself was too small. He argued with them for decades while collecting a salary from the government that always seemed to disappoint him.

Dan Breen was an unrepentant man. He did not regret his service and did not show remorse for any of his actions. By the end of his life his bellicose bragging and tough guy personality was matched only by his bitterness at the way things had turned out. He liked to point out that he had fought for freedom, not for democracy and that distinction was quite important to him. Ireland’s democracy seemed to fill him with resentment and disdain, even though he served within it as a politician for years. He died on this day in 1969 at the age of seventy-five but his freedom fighting legend lives on. Many still revere the man and his memoir is still one of the most popular and recommended books on guerilla warfare and Irish revolutionary history in the world.