In chapter seven, Tom Buchanan confronts Jay Gatsby in a New York City hotel about his criminal background and occupation as a notorious bootlegger. At this point in the story, Tom Buchanan has discovered that his wife is carrying on an affair with Jay Gatsby, and his own mistress will be moving far away with her husband, George Wilson. Tom is incensed and tells Jay Gatsby that he has conducted an investigation into his background. Tom proceeds to tell Daisy that Gatsby is business partners with the shady Meyer Wolfshiem, and the two men sell illegal grain alcohol over the counter of drug-stores. According to Tom, Gatsby and Wolfshiem own numerous drug-stores throughout Chicago where they conduct their bootlegging operations. Tom then mentions that a man named Walter Chase told him that Gatsby is also involved in an illegal gambling enterprise. In addition to Gatsby's bootlegging and gambling operations, Tom also hints that Gatsby is involved in something much more ominous and illegal by saying,

That drug store business was just small change . . . but you’ve got something on now that Walter’s afraid to tell me about" (Fitzgerald, 143).

Tom has made an investigation into Gatsby's occupation by the time the reader arrives at the middle of chapter 7. This investigation has revealed to Tom that Gatsby could not have spent four years at Oxford, and that Gatsby's services are less than moral.

Tom reveals that Gatsby is connected to Meyer Wolfsheim for work purposes and that Wolfsheim is a swindler. The most specific Tom gets in describing Gatbsy's work occurs in these words:

I found out what your 'drugstores' were.... He and this Wolfsheim bought up a lot of side-street drug-stores here and in Chicago and sold grain alcohol over the counter. That's one of his little stunts. I picked him for a bootlegger the first time I saw him, and I wasn't far wrong.

Gatsby asks Tom what's so wrong with that, thereby admitting that this is indeed part of his line of work. Tom later insists that Gatbsy is up to something even more immoral, so much so that Tom's friend won't reveal the secret to him.