Playing in his fourth NBA season, Layman saw action in Minnesota's first 14 games, starting twice. Layman made his Timberwolves debut on Oct. 23, scoring 10 points and recording two rebounds as Minnesota eked out a one-point win over Brooklyn. On Nov. 2 against Washington, Layman scored 14 points and added three rebounds. He made his first start for Minnesota on Nov. 16 against Houston and scored 21 points while adding five rebounds and two assists. Layman suffered a left toe sprain on Nov. 18 against the Jazz, and the injury forced him to miss the next 39 games. Layman returned to action against the Mavericks on Feb. 24, playing 13 minutes off the bench. He appeared in the Wolves' final nine games before the season was suspended on Mar. 11. In those nine games, Layman averaged 7.0 points and 1.8 rebounds in 15.2 minutes per game. Against Orlando on Mar. 6, Layman posted 14 points, two rebounds, one steal and one assist. Minnesota was not one of the 22 teams to participate in the resumption of the NBA season in the Orlando bubble.

Layman took a huge step forward with the Trail Blazers in 2018-19, establishing career highs in nearly every category. Evidently benefiting from extensive Las Vegas Summer League action, he erupted for a game-high 28 points in a preseason contest against the Suns, which helped him secure a spot in the regular-season opener. His versatility rendered him an adequate fill-in for Maurice Harkless at his natural small forward position, and he even stepped in for C.J. McCollum when the established guard missed time in March with a knee injury. The Maryland product ended up averaging 18.7 minutes, 7.6 points (on a 50.9 field-goal percentage), and 3.1 rebounds in the regular season. Naturally, his usage rate spiked to a personal best 22.4 percent. Arguably his best game of the season came on Feb. 5 during a loss to the Heat. Layman posted 25 points on 11-of-17 shooting, eight rebounds, two assists and a steal across 33 minutes. After Portland acquired Rodney Hood in early February, Layman stayed the course and fashioned 10 double-digit scoring performances leading up to the postseason. He finished the campaign with four 20-point games and two contests with at least 10 boards. On the defensive end, he posted three or more blocks twice and at least one steal on 24 occasions. Even with Terry Stotts opting for a more experienced lineup in the playoffs, Layman saw the court in five appearances across three series.

In his second NBA season, Layman once again played in exactly 35 games with one start. The Maryland product averaged 1.0 points, 0.5 rebounds and 0.3 assists per game across 4.6 minutes of action for the Trail Blazers. His rate stats ticked up a bit from the prior season, with his 3.6 rebounds per 36 minutes, 2.5 assists and 1.4 steals per 36 minutes were all improvements over his rookie campaign. Layman set season highs with eight points and five rebounds against Golden State on Dec. 11, and he picked up a season-high two steals against Phoenix on Oct. 18. Layman's season high in blocks was also two, which he recorded on Nov. 24 against Brooklyn. The 23-year-old got a taste of playoff action for the second straight year as well, as he saw seven minutes on the court in Game 3 of the Wolves' first-round loss to New Orleans.

A second-round pick by Orlando in the 2016 NBA Draft, Layman was traded to Portland on draft night. He split time between the G League and the NBA in his rookie campaign, ultimately making 35 appearances (one start) with the Trail Blazers. The Maryland product finished with 2.2 points and 0.7 rebounds per game across 7.1 minutes per contest. Per 36 minutes, Layman averaged 11.3 points and 3.5 rebounds. He also chipped in 1.3 steals per 36 minutes. In eight games with the G League's Windy City Bulls, Layman saw extended playing time, averaging 33.4 minutes per contest. The 22-year-old averaged 17.9 points, 6.0 rebounds, 2.0 assists and 1.6 steals per game across those eight appearances. With the Trail Blazers, Layman scored a season-high 17 points against Golden State on Nov. 1. He went for double figures one other time, netting 10 points against New Orleans on Apr. 12 -- a game in which he also recorded a season-high three assists. Layman notched a season-high four rebounds on two occasions.