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Ryan Rollins has less time on his two-way deal than it appears

January 25, 2025 by Brew Hoop

NBA: Orlando Magic at Milwaukee Bucks
Jeff Hanisch-Imagn Images

The young Buck has five weeks left before he’d need a standard contract to remain with the team.

Recently, I discussed Bucks two-way guard Ryan Rollins’ situation vis-a-vis his dislocated shoulder, which he’s playing through. Within that piece, I mentioned a rapidly approaching deadline on this contract, at which point he’d need to be converted from a two-way to a standard deal, necessitating a standard roster spot. With Milwaukee’s roster currently full, they’d have to open one via trade by February 6th—the NBA trade deadline—or by waiving one of their current 15 standard-roster guys, which can happen at any time.

Who and how are topics for another day. First, we need to find out just how urgent opening a spot is if the Bucks want to keep Rollins. The 2023 collective bargaining agreement between the NBA and NBPA states that “no player under a Two-Way Contract may be on the Active List for more than fifty (50) games during a Regular Season.” We’re just past the midpoint of the NBA season, and 40 games remain. While Rollins has appeared in 26 of Milwaukee’s first 42, he doesn’t have 24 left.

Because Rollins was on the active list for eight additional contests but did not get on the floor, he actually has just 16 games left in which can dress before he hits the limit. Two of those where he was active but didn’t play were DNP-CDs in the first two weeks of the season, another three came in late November after his shoulder injury, two more were in early December after he saw garbage time minutes in two prior outings, and one came two weeks ago today. He saw no minutes in any of those matchups but they still count towards the 50-game limit.

For the record, Doc Rivers and the team are well aware of this ticking clock:

It’s just the number of games. And so for us, if we think he’s that valuable, at some point, we would have to convert him to a full-time contract… We’re gonna play who needs to play, and at some point we need to, we should make a change, we will, if he proves that. You know, this is a competition always. And if not, we’ll try to save as many days just as we can.”

If how Rivers has used Rollins in recent weeks is any indication, Rollins has proven himself. He’s the best option the Bucks have to back up Damian Lillard at this point, and that’s how he’s being utilized.

This has never before been a problem for the Bucks because they haven’t had a two-way player look this good or be this impactful in his first season with the team. Now, however, decision time is approaching faster than you might realize just by looking at Rollins’ Basketball Reference page. Furthermore, two-way players are not eligible to play at all in the postseason, and with how the 22-year-old continues to acquit himself well as a member of Milwaukee’s rotation, he should remain in it.

Rivers generally plays nine guys, so recent injuries to AJ Green and Andre Jackson Jr. have kept Rollins in that mix. When those two, Gary Trent Jr., Taurean Prince, and so on going up the roster are healthy, though, the Bucks shouldn’t make him a healthy scratch. If Rollins suits up for the next 16 games, he’ll reach the limit on February 27th versus the Nuggets, thanks to the All-Star break, buying the Bucks a little more time. From March 1st onward, he’d have to be in the G League, where he hasn’t actually played this season.

Nor should he! Rollins may very well be the long-term backup point guard for this team or perhaps even develop into something more. Usually, two-way contracts are converted into deals that are only fully guaranteed for the current season but not beyond, even if they last three or four years. Rollins has played well enough to perhaps justify a guarantee next year.

In any case, if he stays healthy, it will be incumbent on the Bucks to open up a spot for Rollins by the end of February. They can then sign him to a standard contract for the rest of the year and likely beyond. It won’t be at all expensive in the grand scheme of things, and its reward considerably outweighs its risk. Milwaukee already has two young guards in their rotation on cheap, long-term deals, and I expect them to make it three sooner rather than later. That decision is due sooner than you might think.

Filed Under: Bucks

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