Ryan Rollins was the Bucks’ biggest success story last season, not only for his play on the court but also how much he exceeded expectations. Rollins massively outperformed his contract, but the Bucks will have to pay up soon enough. He’s in a perfect position to thrive next season too and decline his $4 million player option for the 2027-28 season.
Rollins is getting a lot more on his next contract
After Rollins’ huge breakout last season, the Bucks consider him an essential part of their future. He practically averaged 17 points, 5 rebounds and 6 assists per game while being a top contender for Most Improved Player. All of that came on a $4 million salary.
Rollins is already playing much better than his contract and he should only get better. Next season, we can expect the Bucks to put the ball in his hands even more and potentially trade away some veterans on the roster. He’s still only 24 years old and has room to continue improving.
The Bucks will be in a tricky position
Milwaukee will need to navigate its negotiations with Rollins deftly to keep him happy but also affordable. Their current long-term outlook depends on their ability to keep Rollins with their promising new rookies, especially Brayden Burries. But the Bucks have a busy season ahead with potential trades and extensions for multiple other players.
Obviously Rollins will expect a big bump up from his current salary. The Bucks should be happy to pay it too, but the exact value of his next contract is still in flux. Even for a rebuilding team like the Bucks, it’s essential to balance the cap sheet and look ahead to the cumulated value of extensions.
If Rollins demands too much money, the Bucks could consider a shocking option: trading him. Rollins might have his peak trade value now as an uber-low contract who could still contribute as a starter on most contending teams. His new team would want to figure out a longer-term extension, but they can work that out after handing the Bucks some juicy draft capital first.
Rollins’ impending free agency has snuck under the radar because so many other Bucks will face some form of free agency next summer. Rollins is the only one with a player option, but others have team options or outright expiring contracts if they don’t get extensions.
The Bucks need to treat Rollins with more urgency because it’s practically a guarantee that he will decline his player option. He deserves more money and he will get it one way or another. For Milwaukee’s front office, it’s now a matter of figuring out how to get the best value for Rollins - whether in his play on the court or through a trade return.
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