Signed for £1.7 million by Walter Smith in October 2000, Naysmith, a 21 year-old left back and former Scottish PFA Young Footballer of the Year, was already a Scotland international and veteran of nearly 100 league appearances by the time of his arrival. Hailed as one of his country’s most promising footballers, in a way Naysmith came to symbolise for Evertonians Scotland’s decline as a footballing power. In the past, such Goodison greats as Alex Young, Jimmy Gabriel and Graeme Sharp were frequently omitted from the Scotland team; Naysmith, by contrast, was an international regular even at a time when he couldn’t make the Goodison bench.
Initially a quick overlapping full back, Naysmith’s pace seemed to diminish over time – perhaps as a consequence of the injuries that often plagued his time on Merseyside. Utilised as both a full back and auxiliary left midfielder, he showed occasional dead ball prowess. Never was this more in evidence than when he struck a sweet curling free kick that aided a 3-1 victory against Tottenham on Good Friday 2004.
Despite signing a new three-year contract in 2005, Naysmith found himself an even more peripheral player in his last two years at Goodison. With just a year left on his contract, a £1 million bid from Sheffield United in summer 2007 seemed too good to turn down and the full back was allowed to leave for Bramall Lane.