However, Sailor was in 1898 to join Paisley's other senior club, Abercorn, as a forward and after a season or so from there be recruited South to Liverpool, by then in the English top-flight. There he would remain until 1902 but in truth never win a first-team place, on release returning North, this time to Edinburgh, to Hearts and at inside-left a lost Scottish Cup Final, albeit after two replays. 

It was at that point that Arsenal, then a Second Division team, came in for him but again it did not really work out. After just one campaign he was on the move once more, but this time out of the Football- and to Portsmouth in the Southern League. And, whilst he again only spent two seasons on the English South-Coast, it was perhaps a turning-point with him a late developer. 

In 1906 Pompey finished third. In 1907 it was second, two points behind Fulham, with the London club elected to the Football League. Yet clearly the draw of Scotland was for Hunter still strong. Now approaching thirty he chose to move North once more, this time to Dundee, where for three seasons he would lead the line, in 1909 the club fall short of the league-title by a single point, he win a cap and in 1910 the Scottish Cup, scoring the winning-goal in defeating Clyde, which he would promptly join.

And it was from the Glasgow club that he would make what would be his final one in football. He applied for the job of manager at Motherwell, got it, was player-manager for a year, manager-only for thirty-four more to 1946 and club Secretary for thirteen after that. And unlike today he was given time, which allowed the establishment of the club in the upper half of the First Division, just avoid relegation in 1925 and then field teams that would from 1927 for a decade be in at least the top five, winning the League in 1932. It is an almost unrivalled record, which has meant that Hunter is lauded at the club to this day, with in 2016 the East Stand at Fir Park being re-named for him. 

But behind all the initial, itinerant movement and then eventual stability there is a further personal story. In 1900, whilst at Liverpool, Sailor, recorded as an Iron Turner, had in Paisley married local girl, Elizabeth Eaglesham. However, on her death still in the town in 1903, he was a widower, for the first time and clearly at something of a rootless, loose end. Then, whilst at Dundee, he met and in 1909 married Margaret Watson from Hamilton, which probably was the prompt for his life-changing, 1910 move back to the Central Belt.