with 161 goals from 324 senior matches. In 1928, with Bolton in financial trouble, Herbert Chapman's Arsenal made Jack the first five-digit signing in world football, almost double the previous record; the final fee paid was £10,647 10 shillings. According to Bob Wall, Chapman negotiated the transfer with Bolton's representatives in a hotel bar, his tactic being to drink gin and tonics without any gin in them, while asking the waiter to double the alcohol served to the other side. Chapman remained sober while the Bolton representatives got very drunk, and managed to haggle down the fee to a price he considered a bargain. Intended as a replacement for retired captain Charlie Buchan, Jack was a success at Highbury. He made his debut against Newcastle United on 20 October 1928, and became a regular straight away. He was the club's top scorer for the 1928–29 season. Although less prolific than centre-forward Jack Lambert, he still scored important goals, including the one in the 1929–30 FA Cup semi-final against Hull City which sent Arsenal through to the final, in which Arsenal beat Huddersfield Town 2–0 and Jack became the first player to win the Cup at Wembley with two different clubs. He played in Arsenal's 2–1 victory over Sheffield Wednesday in the Charity Shield at Stamford Bridge in October 1930. Jack continued to feature for Arsenal through the early 1930s, recording a personal best of 34 goals in their First Division-winning season of 1930–31. He won two more titles in 1932–33 and 1933–34. By the time of the latter he was in his mid-30s and reaching the end of his career; competition for his place from new signing Ray Bowden meant Jack played only 16 matches that season. He retired soon after winning his third league medal, in May 1934. Altogether he scored 124 times in 208 matches for Arsenal, making him, the tenth-highest goalscorer in the club's history. He is one of only three players to score more than 100 English top-flight league goals for two different clubs, along with Jimmy Greaves and Alan Shearer. Managerial career After retiring from playing, Jack went on to manage Southend United from May 1934 to August 1940 and then Middlesbrough from November 1944 to April 1952. He also managed League of Ireland side Shelbourne from August 1953 to April 1955. Career statistics 1923 Charity Shield appearance for Professionals v Amateurs 1926 Charity Shield