The Cowboys have learned a series of lessons over the years regarding how and when to negotiate contracts. One of those is on the dangers of extending players before decisions need to be made. Ezekiel Elliott, Jaylon Smith and La’el Collins all represent proactive deals Dallas probably should have waited on.
On the other side of the spectrum are the deals the Cowboys took a wait-and-see approach they later came to regret. Dak Prescott, DeMarcus Lawrence and Dez Bryant all would have commanded less if only Dallas had locked them up earlier.
Sometimes taking a wait-and-see approach is good business. Other times it’s just delaying the inevitable and possibly even making things worse. In the case of cornerback Trevon Diggs, a case can be made it’s the latter.