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A man bet €60 on two horses and believed he had turned it into €319,440. Ladbrokes refused to pay, citing a racing investigation he wasn’t part of. He launched High Court proceedings, and a year later he got a fraction of it. – Dylan Phelan, 25, from Dungarvan in County Waterford, worked at a racing stable for trainer Declan Queally. – On April 19, 2024, he walked into a Ladbrokes shop in Limerick City and placed a €30 each-way double on two of Queally’s horses. – He took Ladbrokes’ early prices of 80/1 and 125/1. – Rocky’s Diamond won a maiden hurdle at Limerick, and 22 minutes later Diamond Nora won a mares’ maiden hurdle at Ballinrobe. – His €60 stake had become €319,440. – But when he went to collect, Ladbrokes wouldn’t pay. – The company said it would hold the bet until the Irish Horseracing Regulatory Board finished investigating the two races. – Race stewards had referred both winners to the regulator because of their apparent improvement in form. – The regulator confirmed that Phelan was not under investigation. – Other bookmakers had paid him on smaller bets on the same horses. – Ladbrokes’ shop terms capped the payout on a bet like his at €100,000. – Phelan said the investigation had nothing to do with him. – Ladbrokes said it waits for an investigation to finish when a sporting body is looking into events it has taken notable bets on. – Phelan launched High Court proceedings and waited for a hearing date. – More than a year later, his story went public and spread to millions of views online. – Eleven days later, in April 2025, Ladbrokes agreed to settle the bet after talks with the regulator. – He was paid €100,000, not the €319,440 on his ticket. He risked €60 on a double that won €319,440. Both horses won, the regulator cleared him, and he waited a year while Ladbrokes held his money. In the end, he was paid, but only a third of what his ticket said.