Anfernee Simons dropped 30-plus points for the third straight game on Monday, the longest streak of his burgeoning career, leading the new-look Portland Trail Blazers to a blowout road victory over the defending-champion Milwaukee Bucks. He made NBA history, too, hitting seven triples against Milwaukee to set a new record for the most made threes in the first 30 starts of a player's career.

It wasn't the step-back and side-step jumpers, contested wrong-foot floaters or dazzling array of dribble moves under heavy pressure from Jrue Holiday—arguably the best perimeter defender in basketball—that made Chauncey Billups most proud of another standout Simons performance, though. What really stood out to Portland's rookie head coach is how Simons dealt with the challenge provided by Holiday on the end of the floor.

“I wasn't gonna switch him off of [Holiday],” Billups said of Simons defensively. “This is a part of his development. People are gonna try to attack you, you stand in there, take your medicine. That's how I learned as a young player. A lot of the older players tried to pick on me and they had big games against me, but that's the way you learn. I wasn't gonna switch him off of Jrue.”

Holiday finished with 23 points and six assists on 9-of-16 shooting, pushed into more of a primary offensive role for Milwaukee with Giannis Antetokounmpo resting a sore left ankle. He also accounted for over half of the Bucks' 13 turnovers, coughing the ball up seven times—Holiday's second-most turnovers in a game this season.

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The Houston Rockets invested heavily into Fred VanVleet during the 2023 offseason. Houston gave the point guard a three-year, $128 million deal in a move that was meant to turn the Rockets from a rebuilding team into a championship contending one. The signing did just that, as the Rockets finished the 2024-25 regular season as the two-seed in a stacked Western Conference. VanVleet was the veteran presence and 3-point shooter that the team desperately needed, and he still might have a role with the Rockets going forward. Houston has a team option on his contract for next year, and they very well may pick it up. The Wichita State product reportedly wants to stay in Houston, but the point guard would be set to make over $44 million next season under his current contract. The Rockets and their guard recently pushed back the deadline on Houston's decision with VanVleet, and although reports suggest that they are interested in writing up a new, long-term deal, it isn't necessarily a guarantee that VanVleet will be playing for Houston next year. The Rockets blew him away with an offer he couldn't refuse back in 2023, and another team could so the same when/if he hits the open market this offseason. If VanVleet does become an unrestricted free agent, which teams outside of Houston would make the most sense for him to sign with? 1. Orlando Magic Jalen Suggs and Franz Wagner recently signed big deals with the Orlando Magic, and Paolo Banchero will be getting a mega contract extension here soon. Because of that, the Magic no longer have money to blow like they have had in recent years. That will make a deal for another big ticket free agent hard to pull off, especially considering the team signed Kentavious Caldwell-Pope last year. If Orlando can make the money work, though, then Fred VanVleet would be a great fit with the Magic. The Magic finished dead last in 3-point shooting this season, and VanVleet has made at least 2.5 deep balls per game in every season since 2018-19. VanVleet can hit shots form behind the arc off of the bounce or in catch-and-shoot situations. The Rockets were heavily reliant on his shooting expertise, so the guard would have plenty of familiarity getting up deep shots with high volume if he signed with the Magic. While undersized, VanVleet is a pesky defender, so he'd fit right in with a Magic team that has one of the best defensive units in the league. VanVleet could play alongside Suggs and give opposing teams fits. Ultimately, though, the Magic just need more shooting to get to the next level, and VanVleet is arguably the best shooter who could be available on the open market this offseason. 2. Brooklyn Nets A more realistic option for a VanVleet destination would be the Brooklyn Nets. The Nets are set up to have the most cap space this offseason, and they have a major need at point guard. With D'Angelo Russell and De'Anthony Melton hitting free agency this offseason, the Nets don't have a true point guard under contract for next season. Brooklyn needs to spend big this offseason, and they'd be smart to offer VanVleet a contract big enough that he'd have no choice but to leave Houston. VanVleet averaged 14.1 points per game last season, which was his lowest mark since 2018-19. He is trending the wrong way, but he still has enough left in the tank to give the Nets a few good seasons. 3. Portland Trail Blazers In the same way that the Rockets were looking to take the next step in 2023, the Portland Trail Blazers could use VanVleet's presence to get over the hump. The Trail Blazers have plenty of big man depth, as centers Deandre Ayton, Donovan Clingan, Robert Williams, and Duop Death are all under contract next season. Portland also has a lot of wing depth. Deni Advija started to look like a star late this past season, Toumani Camara is an elite defender, Shaedon Sharpe is a freakish athlete, and Jerami Grant is a proven scorer. The team is thinner in the backcourt, though. Anfernee Simons is a solid scorer, but Scoot Henderson has looked like a fringe draft bust since being drafted third overall. Portland shouldn't give up on Henderson completely, but there wouldn't be any harm in signing another guard. Like the Magic, the Blazers were one of the worst 3-point shooting teams in the NBA. VanVleet would improve that weakness, and in a stacked Western Conference, Portland needs all of the help they can get if they are to compete for a playoff spot.
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“They kept trying to back [Simons] down, kept trying to chase him. I thought Ant did a really good job defensively against him,” Billups said. “He had seven turnovers in the game, and he's one of the best the game has to offer. I was most proud of that with Ant as opposed to obviously the big numbers he put up. But defensively, he had to really scrap tonight.”

Simons doesn't bear full responsibility for Holiday's uncharacteristically sloppy play with the ball. Portland switched across four and sometimes five positions on Monday; both Jusuf Nurkic and Trendon Watford fared well at times when matched up with Holiday one-on-one. Josh Hart, Justise Winslow and C.J. Elleby, to no surprise, were more aggressive and disruptive checking the Olympic gold medalist than Simons. The Blazers' help defense in pick-and-roll situations was consistently on time and well executed, too.

Portland's on-the-fly rebuild faces countless questions, but among the most important is whether their new star backcourt can hold up defensively better than their last one. Simons is essentially the same size as C.J. McCollum, and hasn't exactly been average on defense since first becoming a fixture of the Blazers' rotation last season.

But the unknown begets possibility, and Simons is still far from a finished product. Inspired by the relentless activity and intensity of his revamped team, maybe Monday's game proves a crucial turning point for Simons' defensive mettle.