Haywood Highsmith’s career in the NBA hasn’t been an easy one. He went undrafted in 2018, spending the majority of his rookie season playing in the G League before making his official NBA debut with the Sixers. It wasn’t until two years later that everything changed for him, after signing with the Miami Heat.

He signed a 10-day contract with the Heat in December 2021. Little did he know that three and a half years later, he’d still be in Miami. The 2025-26 season could be his last, though.

The Heat re-signed Highsmith to a two-year, $11 million fully guaranteed deal last summer, so this upcoming season is the final one on his current contract. As an unrestricted free agent next offseason, he could leave Miami.

Highsmith has come a long way since 2021. He might’ve begun his NBA career with the Sixers, but he developed into an NBA player with the Heat. Miami has a knack for uncovering hidden gems, with Highsmith being no different. He has built a reputation as a player who can do a little bit of everything, but he specializes on the defensive end, which is why he earned the “locksmith” nickname.

Haywood Highsmith is entering the final season of his contract

Highsmith averaged a career-high 6.5 points, 3.4 rebounds, 1.5 assists, and 0.9 steals per game last season in 74 contests (his career-high in games played), shooting 45.8% from the field and 38.2% from three. He started 42 games, eventually being replaced by Kel’el Ware in the starting lineup.

The forward is one of the most productive role players in the league, with his role shifting at times on a nightly basis. He’s known for being a lockdown defender, but he can score, too. Highsmith poured in 17 points in 27 minutes on 6-of-7 shooting from the field and 5-of-6 from three in the Heat’s Game 2 loss in the playoffs to the Cavaliers. It was Miami’s most competitive game against Cleveland in that series.

Highsmith’s future with the Heat is uncertain. He drew interest from several teams as a free agent in 2024, and that should be the case again in 2026, especially if he boosts his shooting percentages. He’s the kind of role player you want on your bench.

The upcoming season could be his curtain call in Miami. Highsmith might be the next undrafted gem to leave the Heat, a bittersweet moment for fans to prepare for as they watched his journey unfold over the past few years.