I find it extraordinary that almost every discussion on whether Dak Prescott should get a new contract is centred around the $59,455,000 cap hit in 2024 season, with a further $36m cap hit pushed into void years. Cleary Dak is an elite QB during the regular season but so far seems to be a nervous wreck in the play-offs. He was drafted in 2016. While I'm not a Dallas fan, I would be very cautious about assuming Prescott will be able to get his act together in the play-offs; in which case, why is he worth huge money, or even the starting QB role in the medium to longer term ?
Dak signed a 4 year deal for $160m. On signing, $95m was fully guaranteed. The cap hit in year 1 was $17.2m, year 2 it was $19.7m, year 3 it was $26.8m. Whoever agreed this deal/restructure on the Dallas side needs to be fired. Towards the end of the deal, Dallas needed to be in position where they could make an assessment based on Dak's performances, not the financial side.
Spotrac has a good article on the subject, also came up in at least one of their podcasts I listened to; all the options look awful to me. Still, I would be very reluctant to give Prescott a new contract unless he performed at a decent level in the play-offs next season. Solving 2024 cap issues simply creates even worse problems in the future.
https://www.spotrac.com/news/the-cowboys-financial-options-with-dak-prescott-2142/