Richard Sherman, with the help of his wife, negotiated his own contract with the 49ers in 2018, a decision that was roundly criticized by all the "experts."
Sherman signed a three-year contract with the 49ers that was worth up to $39 million. However, only $3 million was guaranteed, and it was, at its core just a one-year deal worth $7 million. Since the cornerback was coming off a ruptured Achilles, many thought he was taking a gamble by not trying to get as much money as possible. Instead, Sherman bet on himself, negotiating a contract with little guaranteed money, but one that was loaded with incentives to reward him for stellar play and escalate his base salary the following season.