The arrival of left back Jack O’Donnell from Darlington at the end of January 1925 saw Everton plunged into one of the most bitter transfer disputes of the era.  The Everton board had sanctioned a £4,000 double purchase of the defender and the Darlington forward, Tom Scott.  The joint bid was accepted and O’Donnell became an Everton player, but Scott delayed and a week later emerged as a new signing for Liverpool.

A furious Will Cuff announced immediately that Everton would take action with the FA, the Football League and, if necessary, a civil court. ‘We have legitimate grounds of complaint against Darlington Club,’ he said. ‘We consider their action should be subject for inquiry.’ Darlington insisted that they had done nothing wrong and merely gave the player a free hand to decide who he should join.  The matter was eventually resolved the following August, when Darlington compensated Everton to the tune of £250.

The player Everton got from Feethams for a fee of £2,700 was considered by the Daily Courier ‘one of the most promising defenders in the country’.  In acquiring him Everton saw off the interest of Liverpool, Cardiff City, Blackburn Rovers, Leeds United, and reigning champions, Huddersfield Town.  Standing 5ft 8inches tall, O’Donnell was a muscular player who had been converted from centre forward to defence.  For a stretch of the 1925/26 season he would partner Dixie Dean as inside left, a local newspaperman reporting ‘What his play may have lacked in polish; it undoubtedly atoned for in dash and vim.’

But it was at left back that he made his reputation. ‘O'Donnell's work roused the admiration of the home spectators,’ reported the Daily Courier’s ‘McN’ of an early outing at Bury. ‘The Darlington lad had a fast wing to face, but he stood up to them in great style, his interventions being splendidly timed and his kicking strong and of good length.’

O’Donnell was ever present as Everton lifted the League Championship in 1928 and missed just a single game in each of the following two campaigns, the latter of which ended in the ignominy of relegation.  O’Donnell was, nevertheless, something of what could euphemistically be described a ‘colourful’ character.  In August 1930 a board minute recorded that he was ‘suffering from a disease owing to his own misconduct’ The defender was suspended for 14 days and never played for Everton again. Reading between the lines it seems as if he picked up some sort of sexually transmitted disease – the ‘ungentlemanly’ conduct of the day.

In December 1930 he was sold to Blackpool for £2,500, but disciplinary problems followed him and his contract was eventually terminated. He played out his career in the lower leagues and in Dublin.