In November 1975 he flew out to Saudi Arabia for a trial at top-flight Al-Hilal, as manager George Smith, the man who had signed him at Stalybridge, offered him the chance to earn a tax-free contract in the oil-rich nation. He impressed on the trial and was offered a contract, this made him the first European to play professionally in Saudi Arabia. Club president Prince Abdullah bin Nasser bin Abdulaziz Al Saud bought O'Keefe a Pontiac Ventura, before taking the young player on a luxurious tour of Europe, visiting five star hotels in London, Paris, Cannes, and Rome, before returning to Riyadh for the start of the new Saudi season of football. However, on the trip he asked O'Keefe to give up his football career to become his lover, and was refused. As Prince Abdullah was such as a wealthy and powerful man in Saudi Arabia (a member of the House of Saud), O'Keefe fled the country, fearing for his safety. As he needed Prince Abdullah's permission to leave the country, O'Keefe had to convince him that he was only going to stay in England for one week so as to visit his ill father (who was in fact in good health). Upon his return he informed The Football Association, who gave him advice after forming an emergency meeting.