As a schoolboy, I have vague memories of him playing against City in the late fifties / early 60's when 'Boro were big rivals.

He always seemed to score and always incurred the wrath of City supporters - which he appeared to enjoy doing! Of course no-one had an idea he would go on to become a legend as a manager. Must have been quite a character.

Another prolific centre-forward from those years comes to mind - Tommy Johnston, who I recall as a Leyton Orient player but on looking at Wiki I see he played for 8 different clubs over 12 seasons scoring 256 goals in 425 appearances:

1949–1951 Kilmarnock 19 (17)
1951–1952 Darlington 27 (9)
1952 Oldham Athletic 5 (3)
1952–1954 Norwich City 60 (28)
1954–1956 Newport County 63 (46)
1956–1958 Leyton Orient 87 (70)
1958–1959 Blackburn Rovers 36 (22)
1959–1961 Leyton Orient 93 (51)
1961 Gillingham 35 (10)
Total 425 (256)

You'll notice he was with Orient twice, scoring 121 in 180 games. Another nasty bugger, too!

Any other old-timers recall seeing these guys?