In 1965, when the club was looking to sign a new inside forward, Sid offered the position to David Barlow, overruling some of the club's other directors who wanted Ian McCormick of Partick Thistle. David had recently quit the game after getting injured, but was tempted back on the promise of two years as player coach on £35 a week.
David was also employed to run the social club as social and sports officer. Two months into his Athletic career, he threw a party at the venue where he threatened to bar rowdy workman Johnny Nicholls for pinching his fiancée Irma Ogden's bottom. Sid reprimanded David for the act, as it exceeded his authority.
During a benefit match in December that year, David was tackled by Larry Palmer and tore a ligament, forcing him to retire from football permanently. Sid was forced to dismiss David from his position at the social club - a gesture which caused David's new father-in-law Stan Ogden to row with him - but out of sympathy he offered David a job as engineer on his factory floor. David eventually turned the job down in favour of buying the Corner Shop.
In 1970, Sid carried out a £1,200 job for Alan Howard but received no payment from the man he considered a friend. Sid got together with some of Alan's other creditors, including Willie Piggott, Joe Makinson, Ray Langton, Irma Barlow and Annie Walker, who collectively threatened to sue Alan if he didn't pay up. In response, Alan convened a meeting at the Mechanics Hall where his accountant P.H. Vine asked the creditors for time for his client to get his affairs in order. Len Fairclough proposed a moratorium agreement giving Alan three months - a proposal rejected by Sid, who reminded the audience of the contempt Alan had shown them by getting married in the midst of his troubles. Despite his strong words, the creditors voted in favour of Len's proposal. Sid also asked to inspect the deeds of Alan's Leeds salon to verify Mr Vine's claim that it was owned by Alan's ex-wife Dorothea, which Mr Vine obliged.
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