Jack had been with Bolton for eight years, scoring 144 goals in 295 league appearances and winning the FA Cup in 1923 and 1926 (he scored the winner in the latter). But by 1928, the team had become strapped for cash and were looking to sell. Arsenal, meanwhile, were in the market to replace forward Charlie Buchan, who had retired at the end of the previous season.
When Arsenal manager Herbert Chapman first approached Bolton, they agreed to the transfer for a fee of £13,000—which would have doubled the record at the time, set when Sunderland bought Bob Kelly from Burnley for £6,500 in 1925. According to club legend, Chapman met with Bolton representatives in a London restaurant, where he instructed the bartender to secretly leave the alcohol out of his drinks. While the others at the meeting proceeded to get drunk, Chapman remained sober and used the advantage to negotiate the purchase price down, though it still set a new world record.
Jack remained with Arsenal for six seasons, scoring 113 goals in 181 league appearances and winning the club's first FA Cup in 1930. In the 1930-31 season, he scored 31 goals to help the club to their first league title, then won additional league titles with them in 1933 and 1934 before retiring at the end of the 1933-34 season.
[For more about the transfer, including different stories about the negotiation, visit http://www.blog.woolwicharsenal.co.uk/archives/4770.]
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