NBA Free Agency: Five contracts teams will regret giving out this offseason

3. Anfernee Simons: 4yrs, $100M (Portland Trail Blazers)

Just minutes after free agency officially began Thursday evening, ESPN’s Adrian Wojnarowski reported the Portland Trail Blazers agreed to a four-year, $100M contract extension with 23-year-old guard Anfernee Simons.

The 24th overall draft pick in the 2018 NBA Draft is coming off the best season of his young career. Simons averaged career highs in points (17.3), assists (3.9), and minutes per game (29.5) last season and shot at least 40 percent from the perimeter for the second consecutive season.

He showed steady improvement playing as a backup the past couple of seasons, but he really started to take off when he was thrust into a more prominent role in the absence of CJ McCollum and Damian Lillard last year. The game really seemed to slow down for Simons last season.

While enjoying an increased and more consistent role, he really began to show flashes of brilliance. He showed off some fancy handles, an improved ability to finish through contact at the rim, and an aptitude for knocking down tough shots off the dribble. He played with a certain confidence and fearlessness you want to see if you’re a coach or a fan.

After playing solely off the bench in 2021, he started a career-high 30 games last season. During that span, Simons averaged 22 points and 5.5 assists in 34.3 minutes per game with efficient shooting splits of .452/.415/.871. He scored at least 30 points in six games, including a career-high 43 points in a five-point victory against the Atlanta Hawks. 

After reading all that, you’re probably wondering why Portland would regret this contract? Look, Simons is a fine player with loads of potential and the tools to be that player to replace CJ McCollum as Lillard’s Robin. The problem is Portland experimented with the undersized backcourt idea for the past six seasons, and it hasn’t worked. 

Going from CJ to Simons saves you a little money, but you still have two traffic cones on defense running around the backcourt. While AnferLillard should be an exciting duo, it won’t result in much winning basketball in the playoffs.

With Lillard entering his 11th year in the NBA and the final year of his contract before he can opt out and test free agency, this new romance may not last very long.