Anfernee Simons didn't quite see the gravity of his breakout season coming. Entering his fourth NBA season firmly behind Damian Lillard and C.J. McCollum in the Portland Trail Blazers' backcourt, he expected to play a supporting role for a contender instead of cementing himself as a budding star with Lillard watching from the sidelines and McCollum playing elsewhere.

“I didn't expect this,” Simons told Shams Charania of The Athletic and STADIUM. “Sadly, all of the injuries happened and trades happened. It just kind of elevated me to be starting, playing big time minutes each and every game. It's been amazing to see just the maturation of my game over this past year, and just growing from there.”

Simons is averaging 17.0 points, 2.7 rebounds and 3.9 assists per game this season, easy career-highs across the board. But that solid production belies the truly eye-popping nature of his play since Lillard went down before the New Year, a stretch that no doubt helped inform Portland's decision to trade McCollum to the New Orleans Pelicans at the trade deadline.

Over his last 23 games, Simons is averaging 23.6 points, 2.9 rebounds and 6.1 assists, shooting 46.4% overall and draining 41.8% of his nearly 11 three-point attempts per game. He's scored at least 30 points in each of the Blazers' last four games, leading his new-look squad on a 4-0 surge heading into the All-Star break.

It's not just those stellar per-game numbers that convey the extent of Simons' impact, either. Like Lillard before him, the 22-year-old has emerged as Portland's singular offensive bellwether since being empowered as the team's primary ball handler. The Blazers' offensive rating with Simons on the floor in 2022 is 111.8, per NBA.com/stats, and dips all the way down to 99.8 when he's on the bench—a 12-point fall that easily ranks highest on the team.

Simons has saved some of his best moments for the biggest ones, too. As he danced with the ball on Tyus Jones in Portland's statement win over the Memphis Grizzlies, preparing to launch a dagger step-back triple, it was impossible not to think of Lillard so many times doing the same.

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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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Lillard and Simons have shared the same trainer for years. When the Blazers selected the fresh-faced, quiet teenager out of IMG Academy with the 24th overall pick in the 2018 draft, Lillard made a point to take Simons under his wing.

Some three years and counting later, Simons credits his meteoric rise to the influence he continues to receive from Lillard.

“It's been great,” Simons told Charania of learning under Lillard. “My first couple years, just learning, just watching. He's always teaching me things, even during the game even when I wasn't playing. He would come over to me and teach me what he was doing in the game, even though he knew I wasn't gonna play. He just knew at some point it was gonna be my time to play and he wanted me to understand each and every situation he was going through. Now you see it coming to life. Me in the game now, I'm going through everything he's been through over the years as well.”

Odds are that Lillard's season is finished.

Portland interim general manager Joe Cronin suggested as much a couple weeks ago, and it seems unlikely Josh Hart, Justise Winslow and the revamped Blazers will take opponents by surprise during the season's remainder like they did immediately after the trade deadline. Remember, there just isn't much incentive for Portland to push for the playoffs by welcoming Lillard back to the lineup. The team's  2022 first-round pick goes to the Chicago Bulls if it falls outside the lottery.

Either way, it's only a matter of time until the Blazers' new star backcourt takes the floor together, with Lillard and Simons serving as the on-court embodiment of their past, present and future.