My understanding of the contract is that it's through the 28-29 season as either a coach, or ambassador. Here's a snippet from online sports publications outlining some of the details concerning this role.
"While Calipari's record-shattering deal in 2019 was termed a lifetime contract, the truth is that it was not. It's simply a lucrative, long-term deal that offers Calipari the opportunity to continue collecting a nice salary until June of 2029."
This contract isn’t guaranteed to last through 2028-29, however. After the 2023-24 season, Calipari will have a chance to opt out of the deal and accept a role as Special Assistant to the Athletic Director. If he were to exercise that option, Calipari would keep his $400,000 base salary for the remainder of his contract, along with an additional $550,000 per year in supplemental pay. That would make his total compensation $950,000 per year.