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McConnell was born in Irvine, Scotland, and grew up on the Isle of Arran. He attended Stirling University, where he was elected head of the Student's Association. He graduated with a BSc Dip Ed and went on to teach mathematics at Lornshill Academy in Alloa from 1983 to 1992. In 1984, aged 22, McConnel was elected to Stirling District Council where he served for 8 years.
His confident, or brash, demeanor in politics has earnt him the nickname "Jumping Jack Flash". An example of his ability to manage his public image was the timing of his statement that he had been unfaithful to his wife, Bridget. He admitted this at the start of his leadership campaign, which prevented the tabloid newspapers from raking up any gossip about his private life during the campaign.