Summary

Holiday may be the best guard in the 2021 free agent class, and could turn that into a massive contract. In addition, since the Bucks gave up so much to trade for Holiday, they will certainly feel pressure to retain Holiday, especially since losing him would not even open up cap space to replace him. Therefore, Holiday will have massive leverage over the Bucks, and may even be able to turn that into something close to a 5-year max. This would likely cost Milwaukee a ton in luxury tax penalties, but it seems like they're willing to pay that.

Holiday may not be an elite shot-creator, but he fits really well as a secondary or tertiary role for a contending team as he can hit shots, defend at a high rate, and be a secondary playmaker. Holiday will be 31 this summer, so teams may be somewhat concerned about the level he will be playing at on the final years of a long-term contract. If losing some athleticism turns him into an average defender and hurts his ability to finish on drives, the back end of a big contract could be rough. However, even sub-All-Star level guys can get big money in free agency (see Gordon Hayward), so Holiday should be looking forward to a big payday. It may even be his last big contract.

Cap Considerations

Holiday has a $27 million early termination option for '21-'22. If he opts out, Holiday will be an unrestricted free agent with a $39.3 million cap hold and Full Bird rights. Even if Holiday opts out and leaves, the Bucks will not have cap space barring major trades. The max amount the Bucks can offer Holiday is 5-years, $228.2 million, the same contract that Giannis Antetokounmpo signed last offseason.

Other teams will be able to offer Holiday up to a 4-year, $169.2 million max offer. If Holiday and an over-the-cap team have mutual interest, a sign-and-trade can be explored.

Potential Teams: Bucks, Heat, Bulls, Clippers, Raptors

Predicted Contract: 5-year, $175 million with the Bucks.

Last updated: 4/30/2021