When you have a talented young player on a bargain-value contract, vultures tend to circle above a team, as the Milwaukee Bucks are quickly learning in the case of 24-year-old combo guard Ryan Rollins. A late-second-round pick in the 2022 NBA Draft, Rollins bounced between several franchises and the G League before landing on a two-way deal with the Bucks during the 2023-24 season.
Since then, he's blossomed into one of the most well-rounded young two-way guards in basketball, with an elite defensive skill set as a disruptor and perimeter hound with a sweet handle and nasty jumper. That's the complete package that teams are looking for these days, which makes it all the more clear why this could develop into a problem for the Milwaukee Bucks.
Rollins is making $4 million in the 2026-27 season, with a player option for the following year, and some analysts are already making the case to chase after the Bucks' coveted guard. Over at Pippen Ain't Easy, Andrew Hanlon wrote about why he thinks Rollins is a perfect target for the Chicago Bulls at this stage of their rebuild and how they could acquire him:
"Adding one of the league's most disruptive point-of-attack defenders to the length and athleticism Wilson and Buzelis have on the backline would create a fearsome defense," Hanlon wrote. "Acquiring a budding two-way star like Rollins is the type of move executive VP of basketball operations Bryson Graham needs to be making as he builds a long-term contender in the Windy City."
This is only the first domino to fall, but as Rollins' opportunity grows and teams discover this diamond in the rough on the free-agent market next summer, they'll more than likely be willing to throw serious money in his direction to pry him away from Milwaukee, which will retain early bird rights, but have limitations in what they can do to keep him with the Bucks.
The Milwaukee Bucks need to lock Ryan Rollins into a long-term deal before he gets poached by another NBA team.
Finding and retaining homegrown talent is crucial for any small-market team, but especially Milwaukee because of their last of draft assets over the next several seasons. The Jrue Holiday and Damian Lillard deals cleared out control of their own first-round picks for a long time to come, so there won't be many opportunities for the Bucks to replace Rollins via the draft.
Beyond the business aspects of the scenario, losing Rollins would deeply hurt the Bucks' future by relinquishing one of the best defenders at the guard position with little to show for it. Rollins was one of the best in the league at deflecting passes, chasing down loose balls and standing up to perimeter scorers at the point of attack last year, all while upping his volume as a ball-handler and shooting the lights out from deep.
Sure, the Bucks are deep at the guard position, but this blend of size, speed, strength, and skill is not easily replicated, and it feels as if we're just scratching the surface of what Rollins can become in the long run. So before it's too late, Milwaukee needs to establish its intentions for a future with Rollins in it, and when the time comes for them to offer a contract next year, they can't afford to cheap out.
Rollins has a chance to be a guard of the future for the Bucks, so long as they don't give in to the pressure coming from outside the organization.
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