An
inside forward, Jack started his senior career with his father's club,
Plymouth Argyle, after the war. He played in the
Southern League in
1919–20, and was a member of Plymouth's team for their first match in the newly formed
Football League Third Division in
1920–21. He scored 15 goals in 48 appearances in all competitions. In late 1920 he returned to the town of his birth, signing for
Bolton Wanderers for a fee of £3,500. He spent eight seasons with the Trotters, forming a formidable partnership with
Joe Smith, and between them they scored more than 300 goals. While with Bolton, he made history by being the first person to score a goal at
Wembley Stadium, in the
1923 FA Cup Final; Bolton won 2–0 and Jack earned his first medal. A year later, he won his first
England cap, in a 2–1 defeat against
Wales on 3 March 1924. In eight years he played nine times for his countryfour times as captainand scored three goals. He continued to have success with Bolton, winning the FA Cup again in
1925–26, scoring the only goal in a 1–0 win over
Manchester City. 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, 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 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. He retired soon after winning his third league medal, in May 1934. 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==