The Milwaukee Bucks have found their point guard this season, as 23-year-old Ryan Rollins has stepped up in a huge way and is one of the team’s top performers.
Before he took on the role, though, the Bucks’ point guard position was wide open. The Bucks waived Damian Lillard, who had served as the team’s point guard for two seasons, before the beginning of 2025-26, and reportedly looked at Boston Celtics guard Anfernee Simons during the offseason to replace him.
“Over the summer, the Brooklyn Nets and Celtics discussed several trade scenarios involving Simons that ultimately fell through, league sources told HoopsHype,” HoopsHype’s Michael Scotto wrote. “The Milwaukee Bucks also kept tabs on Simons, HoopsHype has learned.”
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The Celtics took on the final year of Simons’ contract over the summer as they looked to rid themselves of extra salary, and could still do so by trading Simons again. The 26-year-old has exclusively come off the bench this season, and is earning $27.68 million this season.
“Getting below the luxury tax entirely could conceivably be achieved by trading guard Anfernee Simons or shedding the salaries of Sam Hauser and another minimum-salary player,” Scotto wrote. “With that in mind, Boston hasn’t shown a willingness to attach a first-round pick to trade Simons’ expiring contract, league sources told HoopsHype.”
Simons’ Trail Blazers Tenure
Simons had spent the previous seven seasons of his NBA career with the Portland Trail Blazers, and was one of their top producers throughout his time in the Pacific Northwest. In 2024-25, the guard averaged 19.3 points per game over 70 starts.
He led the team in scoring during a disappointing season, and had averaged more than 20 points per game in both of the previous two seasons.
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The Bucks will run a back court of Kevin Porter Jr. and Rollins for the forseeable future, however if they desire an upgrade over Porter at some point this season, they could very well check in on Simons again.
Milwaukee currently sits 11th in the Eastern Conference with a 9-12 record, and will look to improve on Monday, when they travel to the Nation’s Capital for a game against the Washington Wizards at 4:00 p.m. PT/7:00 p.m. ET.
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