Bobby Axelrod reaches a major milestone. Chuck struggles to get his bearings, and he and Wendy navigate a new normal. Tensions are high at Axe Cap now that Taylor Mason is back. Axe faces off against new rival Mike Prince. Taylor wrestles with a decision.

Axe chases a play at Mike Prince's conference. Chuck wrestles with his demons and chooses a new path. Wendy takes the lead as Axe Cap faces a threat. Taylor confronts a figure from their past.

Chuck returns to his alma mater to pursue an opportunity. Axe's big venture is sidelined by a family crisis. Taylor asserts independence with a risky play. Chuck puts Wendy in an awkward position.

Axe must reckon with his past to secure his future. Chuck plots against Axe with the help of some old associates. Chuck and Wendy both try to move on, but get forced together by an emergency. Wendy and Taylor embark on a new venture.

Axe's plans are threatened when an old scheme resurfaces. Chuck wages war on a new front, but a dangerous gambit tests his budding relationship. Taylor looks to make an impact in an emerging field.