Jonny Haynes spent two decades in English football, and did not win a trophy during this period.
Considered to be a fantastic passer.
As a fan with a below average understanding of the game, I find it interesting that most of his international caps were received when he was playing his trade in the second tier of English football. Maybe that's a testament to his quality which would be slightly relevant to your second question concerning legacy. By that, I mean he wasn't playing in the most competitive league, and yet was still introduced in the starting berth for England. Now is this a case that his qualities were recognized by Sir Walter Winterbottom to the point his standing in the game was unaffected by . Or was it relatively commonplace for players to receive caps despite playing in the 2nd division.
Now you mention Harry Kane. A player that has been playing for one club for an extensive period. It's not the most outlandish thing to say, he could be playing for one of the most competitive clubs in world football, he's certainly been desired (in the past) by the likes of Real Madrid, and Juventus. Which is why I find it somewhat pertinent that Haynes had an opportunity to join Milan:
'''I'm very happy about the salary I'm getting, it's not as much as if I'd gone to Italy but I think what I would be losing, it would be best to stay in the country with my family and friends.''
That is a quote from 1961. The 1960-61 season where Milan lost out on the league by four points, they qualified for the Inter-Cities Fairs Cup. The next season they won the Serie A, and therefore qualified for the European Cup.
He also had an opportunity to join Spurs who showed interest in 1964, but he stayed in his comfort zone by staying with Fulham.
In 1961, he came third in the Ballon d'or behind Omar Sivori, and Luis Suárez
At the age of 35 he retired from English football, and as a semi-retired player he joined a league in South African where he finally won a trophy