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Ryan Rollins has the chance to play Tyler Herro out of Milwaukee

If Ryan Rollins plays well enough, perhaps the Milwaukee Bucks could decide to trade Tyler Herro this season.
ByJack Simone
Feb 13, 2025; Dallas, Texas, USA;  Miami Heat guard Tyler Herro (14) reacts during the first half against the Dallas Mavericks at American Airlines Center. Mandatory Credit: Kevin Jairaj-Imagn Images
Feb 13, 2025; Dallas, Texas, USA; Miami Heat guard Tyler Herro (14) reacts during the first half against the Dallas Mavericks at American Airlines Center. Mandatory Credit: Kevin Jairaj-Imagn Images | USA TODAY Sports via Reuters Connect

The Milwaukee Bucks are going to have some tough decisions to make next summer, as a few key players will be entering free agency. Two of those guys are Tyler Herro and Ryan Rollins, the latter of whom has a player option that he seems likely to decline. But Rollins has a chance to replace Herro before Herro even leaves.

Herro just joined the Bucks this summer via the massive Giannis Antetokounmpo trade with the Miami Heat. He’s a one-time All-Star and looks like the type of player who could be a solid second or third option. But he’s going to want a lot of money, and if Rollins can outplay him, the Bucks may be better off trading Herro before he becomes a free agent.

If Rollins can prove that he deserves to be the primary ball-handler in Milwaukee, then trading Herro for draft picks and other pieces could be a worthwhile idea for the Bucks to consider.

Ryan Rollins could play Tyler Herro out of Milwaukee

Last year, Rollins enjoyed a breakout campaign. Even though the Bucks were an absolute mess, he was a bright spot, proving that he has the chance to be a star (or a star role player) in this league.

For the time being, he’s on an incredible contract for his production. This upcoming season, he’s only slated to make $4 million, which is elite compared to Herro’s $33 million.

Herro has played well in recent years. He’s an established 20-point-per-game scorer (when he’s at his best) and has steadily improved as a facilitator as well.

With that in mind, it seems likely that he’ll want a relatively large payday next summer. He’s made an All-Star Team. He’s been to multiple NBA Finals. He’ll want to cash in once again.

Rollins will want to get paid, too. But considering he hasn’t earned a real NBA payday just yet, it seems likely that the Bucks would be able to re-sign him for less than Herro.

So the question is, can Rollins play well enough to the point where the Bucks feel comfortable trading Herro before the deadline this year, so they don’t have to worry about an extension next summer?

That could be beneficial to the future of the Bucks’ roster, and Rollins would get to establish himself as the premier guard in town once again.

Not only would the Bucks be saving money, but by trading Herro, they could add some more draft assets as well.

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