Billionaire Denis O'Brien will crystallise a loss of more than €450m on his investment in Independent News & Media (INM) following its sale to Mediahuis.
The businessman spent an estimated €500m amassing his almost 29.9pc stake in the media group.
Mr O'Brien initially began buying shares more than a decade ago, when now-bankrupt businessman Anthony O'Reilly and his family - which had acquired the publishing company in 1973 - still owned 28pc of the group.
There had been intense rivalry between Mr O'Brien and Mr O'Reilly before the former began snapping up shares in INM.
Mr O'Reilly's Valentia consortium bought Eircom, now Eir, in 2001 ahead of a rival bid from Mr O'Brien.
In 2005, while chairman of Eircom, Mr O'Reilly - once Ireland's richest man - also outbid Mr O'Brien to buy Meteor, the mobile phone company that's now part of Eir.
But with INM's shares having slumped in the past decade, Mr O'Brien had no doubt all but written off his investment in the media group some time ago.
The billionaire has significant other interests, including his ownership of Digicel, the pan-Caribbean and Pacific telecoms group, as well as other assets.
The sale to Mediahuis will see him receive just €43.5m for his more than 414 million shares in the group.
Yesterday, the Belgian-Dutch group said it had already acquired just over half of Mr O'Brien's holding in INM.
Billionaire Dermot Desmond, with 15pc of the company, will get just under €22m based on the 10.5 cent per share being offered.
Mediahuis has now bought just over half his stake in the media group.
The sale to Mediahuis marks the end of another chapter in INM's colourful history.
And after more than a century, it will, for the first time in its history, not be an Irish-owned company.
The media group has continually attracted the interest of Ireland's richest power-brokers.
The Irish Independent was launched in 1905 by William Martin Murphy, one of Ireland's richest businessmen at the time and arguably the country's wealthiest Catholic.
Born near Castletownbere in Co Cork in 1845, Mr Murphy had developed a business empire than included a tram company, a hotel, and Clerys department store in Dublin.
He was described by his great-grandson as a "loyal friend and a ruthless enemy".
With a reputation as a hard-nosed capitalist, Mr Murphy was a pivotal figure in the Dublin Lockout of 1913. He and union leader James Larkin were intensely opposed to each other's views. Mr Murphy was referred to in the 'Irish Worker' newspaper as a "blood-sucking vampire" and the "tramway tyrant".
But Mr Murphy had a strong social conscience, despite the negative image of him that was whipped up by opponents.
A devout Catholic, he was a member of St Vincent de Paul, and was known to pay his workers well - primarily in an effort to keep unions at bay.
The two flagship titles went on to dominate the newspaper landscape in Ireland for decades to come. After Mr Murphy died in 1919, his family retained ownership of the newspaper group until 1973, when the O'Reilly family bought it.