A television producer, doing research for a series, prompts the HSD staff to reflect on the journey that brought them together, and long-held secrets are revealed. Corey's art fund attracts the attention of a dying socialite and causes ethical concerns. Ditto and Marissa confront their romantic feelings for each other.
Ditto is excited to participate in a stockbroker competition. But after he meets the daughter of a Merriweather Marx client who killed himself due to the way the company treated him, he performs poorly in the competition. However when the stock market suddenly drops, Ditto wins because he kept his assets in cash. Meanwhile, Marty agrees to help a possibly corrupt businessman referred to him by Blackstone, and Wesley proposes marriage to Alison.
When Federal Reserve Chairman Alan Greenspan's plane crashes in Alaska, Wall Street is sent into a tailspin. With their $17 million margin called in, HSD desperately accepts a loan offer from investor Gardner Blackstone. Now they must raise $20 million by the end of business or forfeit their company to Blackstone's control.
Despite his initial reluctance, Granville sues Merriweather Marx for racial discrimination. Meanwhile, HSD orchestrates a leveraged buy-out of Wesley Industries that will counter ""the Kaiser's"" take-over strategy — and save the firm. But when ""Ditto"" discovers the name of the venture capitalist behind ""the Kaiser's"" deal, there's more at stake than ""just business.""
With the law suit pending and their assets frozen, ""Ditto"" and his company fight for their financial lives. As HSD prepares to do battle against ""the Kaiser"" for Wesley Industries, in desperation Ditto plays the ""race card"" and advises his friend, Corey Granville, to file a discrimination suit against Merriweather.
""Rookie"" Carson Boyd learns a valuable lesson about ""green mail"" from money-hungry Hunter Lasky. Lasky nets a windfall, but at what price? Meanwhile, tensions rise at HSD when Alison Jeffers tries to close a major deal and discovers that ""the Kaiser"" has his own deal in the works that could spell disaster for the ""Young Turks.""
""Ditto's"" newly formed investment firm, HSD Capital, struggles to stay alive as his grandfather, ""the Kaiser, ""files a law suit against them. Former rival, Hunter Lasky joins HSD, but Alison Jeffers has reason to distrust his motives. Just as things seem to be turning around for the firm, ""the Kaiser"" finds a way to keep one step ahead of ""Ditto's"" firm.
Robert ""Ditto"" Roberts III conspires with four of the firm's top associates — Marty Decker, Corey Granville, Alison Jeffers, and Marissa Rufo — to make a break from Merriweather Marx & Co., one of Wall Street's most venerable and successful firms. Only one thing stands in their way: the tough-as-nails titan of Merriweather Marx, Robert ""the Kaiser"" Roberts, who also happens to be Ditto's grandfather. Ditto's business plan seems solid, but when news of their rebellion leaks to the press, it turns their six-month scheme into an overnight scramble that leaves Wall Street reeling.