Disclaimer: this is a lot of reading (1000 + words)

++*Portlands done wasting Simons prime. Simons is ready to contribute to playoff team and comes home++*

Orlando Receives: Anfernee Simons Malcolm Brogdon Trailblazers receive: Cole Anthony 2025 first-round pick via DEN top 5 protected 2027 first-round pick 2028 pick swap 2029 first-round pick

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Reasoning for Orlando: In my opinion, Orlando needs to start making win now moves, I say that because not only do they have a haul of first round picks for the foreseeable future, but their two franchise players are only 21 and 22 and are currently giving one of the best defensive teams a run for their money in the playoffs. The six year veteran instantly upgrades Orlando’s back court on the offensive end. I mean Orlando is a dynasty in the making, and you need to surround your cornerstone players with players that can carry the offensive load for stretches, be decisive, as well as play off of your stars that face a lot of attention on the offensive end. Cole Anthony has been okay in doing that, but I don’t think it’ll be enough, mainly because he’s supposed to provide scoring off the bench as well as be a capable primary ball handler, which is something that he hasn’t provided when it’s really mattered. Anyways Simons is going into his seventh year and has shown a strong desire to help a team win, and not lose, which is something that must sound very appealing and encouraging to a contending team such as Orlando. He’s a seasoned 7 year guard who has an extremely polished offensive skill set, he’s gifted with physical tools, he can simply take over games, solid facilitater, create for others, scores consistently off the dribble from all 3 levels, can orchestrate a half court offense when called upon, really good balance that calls for some impresive finishes near the rim. I mean he shoots 43% on 18 attempts a game and 38% from outside on 4 attempts, he’d simply improve their mediocre offensive firepower/depth in the non Franz and non Paolo minutes. SImons would simutainiosley compliment Orlando’s defensive idenity as well with his length and athleticism, if Jamahl Mosley can get him to buy in on that end. Simons will give good defenses a tough coverage and hard time when paired with Paolo and Franz, mainly due to the fact that they are all premier scorers with an immense amount of upside still, and teams wouldnt know who to double, especially with Carter Jr. and Sugggs making major improvements in their ability to stretch the floor. Anyways I wouldn’t be surprised if Orlando’s willing or would consider buying Malocolm out, simply due to the fact that Orlando’s solid guard depth has proven they can make the playoffs, not to mention they all fit with Jamal’s defensive identity relatively well. They will also have 16 active players on their roster if they utilize both there picks and re sign Fultz, as well as Harris. Besides, Simons is mainly being traded to Orlando to complement their offense, facilitate and be their primary ball handler for stretches which is exactly what Malcom does. As an alternative Orlando could sell Malcolm for cheap just to get some value in exchange; however the majority of teams that are interested in Malcolm (Lakers Rockets and Knicks) are over the cap so I would assume they are not willing to pay very high. But ultimnatly Orlando has shown interest in Malcom and he's an expiring veteran pressance with a lot of playoff experience, I personally dont realistically see him cracking rotation, even so, he's an effective leader and even better mentor for the inexperienced young guys. Following the trade: Kel’el Ware seems to be the most suitable and best fitting pick around the 19th overall pick; Ware is a 7 footer that stands out with his mobility, his length allows him to serve as a defensive presence, he’s a reliable pick and roll dfneder, stretches the floor, gret rebounder, and his ability to serve as a playmaker is impressive. During free agency, Fultz and Harris are two players you must resign, I'm not sure how much they’d expect but you have got to bring everyones favorite teamate back, and your most capable perimeter defender back. Then let Chuma walk.

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Portland's Reasononing: The Portland Trail Blazers will be paying 181 million to their active roster following draft night. Crazy to think a team that’s only 8 million away from the second apron only had 21 wins. If Portland were to get off of both Simons and Brogdon’s salary and take on Anthony’s salary, they’d only be 4 million above the Cap maximum, that has to sound super appealing, especially when you take the haul of firsts there getting in return into consideration. I mean both Brogdon and Simons have dropped subtle hints that they don’t want to be a part of another team with a losing record. Simons was even recorded expressing his agitation by saying“We don’t want to have another year like this. My sixth year is done now, going into year seven, I want to the opportunity to win.” And I don’t realistically see Portland having a winning record for at least another season. So I suggest they stop “Wasting” Simon's prime, and let Brogdon meteor/help a team with genuine championship aspirations. Brogdon didn’t even sound confident that he’d be back for next season in his end of season interview either. Not to mention Portland’s already accustomed to trading their cornerstone players to let them have a genuine chance to actually play for something. Portland has a solid young core outside of Simons as well as a deep and talented back court for the future, so this trade frees up playing time and will help their back court of the future develop even further since they’ll actually be getting meaningful reps and experience. Sooner than later Simons will most likely request a trade anyways, and this package must sound so tempting when you take the Draft compensation and money there getting off of into consideration. Not to mention Cole Anthony (Portland Native) is a fromer first overall pick and has a bright future ahead of him, a scrappy/gritty defender who I'm positive Chauncey will fall in love with since he identifies as a defensive minded coach. Not only is he a solid POA defender but he jumps out the gym, facilitates, is a decent passer, as well as a solid finisher at the rim (61%). Following the trade Ron Holland should be the targeted prospect in the draft, then maybe Fillipowski. Once free agency comes around you dont really have much to do, no need for big name hunting, just retain your young core and help them develop.