Now that he is multiple years into his job as Portland\u2019s general manager, Joe Cronin must make big decisions soon<\/a>. If he spends another summer without choosing between Henderson and Simons, that would stunt their development and confidence. It is an interesting situation because the guards have reasons why they could be cornerstones of coach Chauncey Billups\u2019 system.<\/p>\n The Case For Henderson<\/p>\n If Henderson is the Blazers\u2019 point guard for the future, he will be more of a playmaker. Scoot has always been a promising passer because he has good vision for his teammates. Henderson also has the special knack of manipulating the game to his whims with his passing.<\/p>\n Henderson\u2019s biggest issue has always been his perimeter shooting. Thankfully, that vastly improved in the 2024-25 season. Henderson kept working hard on improving his shooting, going from 32.5% to 35.4% from three. That is a marked improvement, as he looks more natural with his rock-solid shooting mechanics.<\/p>\n Defensively, Henderson always had the mentality to shine. He is a superb defender at times because he uses all his elite physical traits to compete with his matchup. Scoot is not a mismatch because he stands up to his assignments and plays physical defense against them. With this defensive impact, he fits right in Billups\u2019 system alongside Toumani Camara<\/a> and Deni Avdija<\/a>. Camara, in particular, is the team\u2019s defensive ace<\/a>.<\/p>\n Henderson still has a high ceiling. He has already showcased his potential throughout his first two NBA seasons. That could be enough to grant him a starting spot, which requires a Simons trade.<\/p>\n The Case For Simons<\/p>\n Simons might be the longest-tenured player on the Blazers, but he can still be the Blazers\u2019 point guard. He will be 26 when the 2025-26 season starts, around the same age as his teammates. Players like Camara will be 25, while Avdija will be 24.<\/p>\n Offensively, Simons is the most dynamic guard on the Trail Blazers. Over the past four seasons since he became an established starter, Simons has averaged 19.9 points per game. He is a rock-solid offensive player who can score from anywhere while being a decent playmaker.<\/p>\n Simons has been a mediocre defender since entering the league in 2018. This big weakness could lead to him not fitting in Billups\u2019 system in the long term. The weakness could be his downfall because Billups has always wanted competitive defenders on the team. Simons has been around for a long time, but he has not shown significant improvement on this side of the game.<\/p>\n The offensive potential is still through the roof because the Trail Blazers have a reliable bucket-getter with Simons. However, the defensive issues might be too much to overcome. The likelihood of a Simons trade is high, especially with rumors of him flying around.<\/p>\n What Will Cronin Do?<\/p>\n![\"\"](\"https:\/\/www.rawchili.com\/nba\/wp-content\/uploads\/2025\/05\/USATSI_25786325_168414264_lowres-1024x683.jpg\")
Mar 27, 2025; Sacramento, California, USA; Portland Trail Blazers guard Scoot Henderson (00) dribbles against Sacramento Kings forward Domantas Sabonis (11) during the third quarter at Golden 1 Center. Mandatory Credit: Sergio Estrada-Imagn Images<\/p>\n