If there is one person who is privy to what it is like dealing with the Dallas Cowboys owner, it's quarterback Dak Prescott. Having negotiated two monster deals, one of which was done right before the start of last season,

Last summer, Prescott went through his own contract negotiations with Jerry Jones and the Cowboys' front office. Ultimately, it resulted in him becoming the highest-paid player in league history with a $240 million contract. CeeDee Lamb, who held out of training camp in 2024, also got a mammoth four-year contract worth $136 million.