After a championship season with the Nuggets in 2022-23, Brown began the 2023-24 season with the Pacers before being traded to the Raptors in mid-January. He put together a solid run with the Raptors, averaging 9.6 points on 48.1 percent shooting, 3.8 rebounds and 2.7 assists in 26.1 minutes per game over his final 34 appearances. He topped the 20-point mark twice during the season, both times with the Pacers in the first half of the campaign, including a season-high 30 points on 11-for-16 shooting in a road win against the Heat in early December. During his final stretch of the season with the Raptors, Brown logged a high of 19 points on a 7-for-13 shooting effort in a road win against the Bulls in late January. He also logged one double-double with 13 points and 10 rebounds in a road win over the Nuggets in early March. Despite being linked in trade talks, Brown is on track to start the season with the Raptors and will likely be back in a sixth-man role, which is where he has thrived in the past. He is also likely to see more than a few opportunities to close games, as his defensive ability often helps him spark runs and protect leads in key situations.