This is season 2 I am in, which means this Daytona 500 takes place on February 15, the same date Earnhardt won his first 500 six years prior on that same date. Dear God, what must be going through AB, Wally, and Benny’s minds at this moment? STORYLINES GALORE! #DoItForDale

So have you heard that the Blazers are looking to shop around the 3rd pick and Anfernee Simons for a star forward? Yeah, let's finally get into this.
The Blazers lucked themselves into a rather unique position, both with the pick they got - having jumped from 5th to 3rd in the draft - and with the team who managed to get the 2nd pick being the Charlotte Hornets who are likely to draft forward Brandon Miller over G League Ignite guard Scoot Henderson, with Scoot seemingly falling to 3.
This would make Scoot the 2nd young guard the Blazers recently drafted and their 3rd under 25 guard to play next to Dame...if they weren't trying to shop the pick around.
They have a perfect opportunity to finally do a rebuild...and yet, here we are with yet another rumor about the Blazers trying to build around Dame and get him the help they've left him without for...what, 8 seasons and counting? Like the Rockets who are alleged to be interested in moving the 4th pick, I don't think the Blazers really should be trying to do a two timelines, pseudo rebuild while contending around Lillard.
I also don't think the package they can put together is as great as it's often hyped up to be. As we'll get into, a package around Anfernee and the 3rd pick plus a player or pick or two is quite decent in a vacuum but it certainly isn't good enough to get to get you that Top 10-15 player in the league who can singlehandedly win you a series - if not, a championship. It certainly isn't enough to outbid the likes of the Jazz or, more significantly, the Thunder who may opt for a splash in the offseason as their core develops into a young, hungry playoff team with some greater veteran presence around them.
I'm just going to say it: If Portland really is saying "time's up" and putting together one last effort to compete against Dame, they need to do more than get Siakam, O.G., Karl-Anthony Towns or whichever star's name pops up in rumors leading up to the draft. Not to say those players won't improve the team, but none of them - and yes i'm including Siakam - are good enough to elevate a former lottery team like the Blazers over the past 2 seasons to a Top 3 seed, let alone guarantee a championship.
A duo of Siakam and Dame, Dame and KAT, etc. can be part of one's core championship team but they need the right supporting pieces around them in order to win. To put it mildly, the Blazers...do not have that. Jusuf Nurkic has seen significant regression as a defender and the bench is one of the few to make the Raptors bench look like a bastion of basketball greatness. It shows on the floor and statistically, and it's a large reason why the Blazers have been one of the worst defensive teams in the league over the past, one of the worst when it comes to rebounding and in general being near the bottom of the Western Conference before they pulled the plug on their most recent season in an attempt to tank for a Top 4 pick.
If the Blazers are actually going to commit to Dame, they need to engage in a paradigm shift this offseason. Rework the starting 5, the bench and go all-in getting Loyalty McLoyal the team he should have had around him for years instead of endlessly running it back with minor tweaks to who his #2 is.
That means either getting your pick back from the Bulls and shopping the 4 firsts/3 swaps you can or removing the protections and dealing out the 3/3 you would have to improve the roster. Don't just get Siakam, KAT or whoever and set them up to fail with Damian because it's not fair to either player to put them in that situation.
Go after Buddy Hield, see if Myles Turner or Clint Capela are going to be available, or if the Wolves are desperate enough to sign and trade Naz Reid to recoup some assets after the costly Gobert trade - if not, try signing him with the full MLE. And you don't stop there! However they plan to shake up the roster in this hypothetical scenario, they need to significantly improve the center position/rotation and their bench to give Dame an actual chance of winning a ring with what few years left they have in his prime.
Also fire Chauncey Billups, he's a bottom 3 coach and the only reason I can't say he is not the worst is because I can't say the Raptors coach will be objectively worse/better without knowing who will head either team. He isn't 3rd, that's for sure.
But anyway that's the Blazers prerogative. What exactly could the Raptors see in a potential pick that, presumably, revolves around Pascal Siakam?
Since I can be a bit of a wordy writer, i'm going to add some TL;DR sections for each playepick discussed in this little piece for those that want a quick breakdown.
Note: This is not a trade proposal; this is a compilation of the assets and players who could be included in a trade for Pascal Siakam. Additionally, this is not an endorsement of trading Pascal Siakam, etc. in a deal with the Portland Trailblazers.
Anfernee Simons
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The main player who's been the subject of a contentious discussion between Blazers fans and Raptors fans. Whether you think he's overrated, underrated or somewhere inbetween, it is undeniable that Anfernee Simons would have to be included in the trade at minimum.
I can't speak for the Blazers and I won't pretend to speak for all Raptors fans so let me just say this: I like Anfernee Simons. He's one of the more exciting players in the league under 25 even if he doesn't have the same ceiling as a guy like Zion or fellow player nicknamed "Ant" Anthony Edwards.
A borderline All-Star guard with a combination of shooting prowess and explosiveness, he had a breakout season in 2021/22 when Dame went down due to an injury and thus became the Blazers lead point guard in his absence. He's a genuine 3-level scorer who can splash from outside, pressure the rim for a high-flying dunk and he's effective in the midrange too. If nothing else, it cannot be overstated how nice it would be for this team to have another player who's a reliable, 38.7% from 3 volume shooter on a roster so thoroughly lacking in outside shooting
And before you say it, yes, Anfernee Simons is a point guard. This isn't a case like CJ where his skillset is that of a 2 who can do some playmaking but shouldn't run your offense, Simons does have some issues with dribbling the air out of the ball before making a pass, but he is a point guard. He isn't a typical point, operating more as a shoot-first point like Lillard, but he's still capable of cracking out a notable number of assists while getting buckets; he dished out 6 dimes a game with nearly 28 points in the games he's played without Dame as the lead point.
All 11 of them last year.
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Yeah, you might have seen some posts or stats online of what Simons has done without Damian Lillard; in his breakout season of 2021/22, the Anferno was putting up a similar number of assists and cracked 20 points per game, albeit over a more significant sample size of 30 games. And in 2022/23, Anfernee Simons put up 27.9/2.9/5.7 (2.4 turnovers so an AST/TO of 2.38:1 which is solid) while shooting a staggering 41% from 3 on 11 3s.
Those numbers are impressive in a vacuum; his true shooting of 62% is especially notable. However, they require some context and should be taken with an enormous grain of salt.
For one, it's a very small sample size over a lengthy period of the season where teams haven't had to plan for Simons to be the main guard to focus their defense on. He's still the 2nd option so it's not like there's no film watching or the like, but if Anfernee Simons permanently becomes the lead point guard of a team, opposing teams will gameplan around him and his weaknesses more significantly than the very few times where he's asked to be the lead ballhandler in Dame's absence.
His 2021/22 stats, while still a limited overall sample size, do suggest he'll be able to dish out a similar number of dimes as the lead guard (Dame had been ruled out due to injury during the season so teams did have to gameplan around the Ant for a large portion of the season instead of a handful of games scattered throughout the season) and he still has room to grow as a playmaker but once again, it was only a sample size of 30 games so it is hard to draw much out from the games he played.
Speaking of drawing conclusions from said sample size: Yes the Blazers went 4-7 within that 11 game sample size - and bear in mind this sample included games where the Blazers were still trying to contend while facing a variety of teams i.e. not every team was a playoff or contender. That isn't great, however, Ant was generally not the main reason they lost since the 2022/23 Blazers as a whole were pretty terrible all year, even before they blatantly tanked. The same is also true of his breakout year when the Blazers lost Lillard due to injury, they just weren't a good team.
If there is a point of contention around Simons that one can draw from his past 2 seasons, it's his defense which...it's bad.
It's really bad.
He's improved this season on that end to the point where i'd say he's a better defender than Dame - even if his overall defensive rating doesn't support this, the eye test does - but that's like saying Spencer Dinwiddie is a better defender than Trae Young. While Chauncey Billups hasn't been doing either one of Portland's guard any favors, it doesn't change the fact that being better than one of the worst defenders in the league is not an accomplishment to be proud of. All coaching issues aside, Simons is still a notable negative on that end of the floor. He has a propensity for losing his man via ball watching, he's not great at closing out on the perimeter and he's not a lane disruptor by any means. It's not impossible for him to improve as a defender - he's 6'3 with a 6'9 wingspan and much of his defensive weaknesses come from a lack of discipline - but as of right now when his shots aren't falling he's a major liability on the court and his flaws on defense were not well hidden when paired next to another notably poor defender in Dame.
There are a couple of other habits that Simons needs to address - he could stand to be less trigger happy as a scorer and work more on his playmaking given all the promise he's shown in that area - but that's the main issue with Simons. He's a very skilled guard with a similar approach to the game as Dame on both ends of the floor. And we all know Dame isn't locking down the opposing team's point.
Does Anfernee Simons seem like he'll become a guard on the level of Dame? No but that's a ridiculously high bar to hold him to, especially with the limited opportunities he had and will continue to have when he's behind Dame in the guard pecking order. Anfernee is a good player who often shows glimmers of true greatness on offense but whose defense (or lack thereof) is going to require very careful teambuilding to limit exploiting said defense in the playoffs. Perhaps he'll need to be the full-time point to fully achieve his potential as a playmaker but while he doesn't scream All-NBA caliber, he's someone you can easily see eking out a couple of All-Star nods at his peak and is, at worst, a staring-caliber guard. As for whether he can be the lead of a championship contender...we'll get to that when we talk about the pick he'd come with.
TL;DR - Anfernee Simons is an intriguing young player with upside as an explosive, shoot-first PG but one whose poor defense does mean the team's starting lineup/bench has to be built around carefully to account for his current (and likely ongoing throughout his career) weaknesses.
3rd Pick
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It's whomever is left from Scoot Henderson or Brandon Miller. Maybe you trade down to 4 for some more assets if you're a believer in Amen Thompson, maybe you take Amen if you think he's the best player available and the Rockets won't negotiate for Scoot/Miller but yeah, it's one of those three via the 3rd overall pick.
Before we get into the players, I do want to briefly mention that I actually did a post a while ago on a different sub going over trades involving the 3rd pick and to put it bluntly: The 3rd pick has good value but it doesn't have as much value on its own and trades involving the 3rd pick for an All-Star or even All-NBA caliber player are very rare.
The closest trade to what the Blazers would want in return was in 2000 where the Atlanta Hawks traded the 3rd overall pick to the Vancouver Grizzlies along with Brevin Knight and Lorenzen Wright for Shareef Abdur-Rahim and the 27th overall pick. That 3rd pick turned out to be future HoFer Pau Gasol but no one knew he'd become that at the time. As for what the Grizzlies gave up for the pick, Shareef Abdur-Rahim was not a perennial All-Star nor was he an All-NBA level player. He was a solid player that became an All-Star in his debut season for the Hawks...and that was his only All-Star appearance.
With that in mind, it is a bit wild that it's so commonly suggested that Simons and the 3rd pick alone should be enough to acquire an All-NBA talent like Siakam, especially with how much inflation we've seen in trades for players of that caliber of late or even players who are a step below. Concerns about his contract expiring lowering his value are baffling, as if a team's front office wouldn't talk to him about an extension before making such a trade. Moreover, it's not like the Raptors need to deal him out when they can simply re-sign him in 2024.
Now this year, when Scoot Henderson or Brandon Miller could be up for grabs, the 3rd pick has a lot more value given how highly praised those players are, so let's put aside the debate on what is fair for Siakam for a moment and talk about the presumed 3rd overall pick, Scoot Henderson.
The 2nd best player in a draft class containing the best prospect since LeBron James. He's projected to go 3rd because Charlotte is allegedly interested in taking Brandon Miller at 2nd but we'll touch on that later. For now, let's talk Scoot:

• Henderson is a freakish athlete and a terrific floor general; he racked up an average of 6 assists a night on an AST:TO ratio of 1.94:1 and is a strong option on offense due to his abilities as a slasher
• His usage as the G-League Ignite's offense, be it ball screens or handoffs, displayed his ability to break down a team's defense
  • To delve deeper into his production as an offensive guard, his percentage rate of ball screens (43.7%) is only matched or surpassed by 7 players across the entire NBA. 7!
• Despite the athleticism, Scoot is generally good at controlling the ball and not turning it over due to careless mistakes driving to the basket
• For a guard, he's a pretty solid rebounder and, if nothing else, he puts in the effort on defense even if he's not necessarily someone who screams "Future DPoY"
• Intangibles are hard to really quantify but Scoot is the definition of someone who "has that dog in him" and he's someone you trust down the stretch to make the right move
• He puts in effort on defense but he's only 6'2 with a 6'9 wingspan and, well he's no Kyle Lowry when it comes to taking charges or the like
• His shooting is...a work-in-progress; he tends to default to long 2s which he isn't great at making (38% overall), his free throw percentage is only 75% and his 3-point shooting is a measly 31% off the dribble

Needless to say, there's a lot to like about Scoot; if Victor wasn't in this draft, he'd easily go #1 overall. He's often compared to Derrick Rose or even Russell Westbrook as this uber explosive guard who can seriously pressure the rim while generating solid passes for his teammates which is a good comparison though one obviously hope his outside shooting pans out more like Curry or Trae than Russ or Rose.
Losing Siakam would obviously hurt the team in the short term but as far as what Scoot brings, there is a lot of upside to him that would raise the ceiling of the team in the long run. His ability to get to the rim, combined with his athleticism would make him the perfect guard for a team that thrives in transition like the Raptors. He would also have chemistry with another player the Raptors have been rumored to be interested in/may take at 13 in Leonard Miller as they played on the same team but we'll talk about the 13th pick's potential prospects another time.
For now, let's go over one of the problems with trading for Scoot Henderson if he is still on the board, besides the obvious hypothetical of "he might never become a player as good as the one you're giving up" or "what do you do with Fred when you brought in Scoot and Simons" because what you're really asking is this: Is a backcourt of Scoot/Simons the team's guard duo of the future?
This brings me to my big problem with a “trade for Simons + 3” trade if the 3rd pick does end up being Scoot: A backcourt of two undersized guards, one of whom is unproven against NBA competition on defense and the other of whom has been one of the worst guard defenders in the league is not a duo of guards you can build a contender around in the long-term unless both of them become significantly improved defenders. Or at the very least, it's a duo that has historically not led to notable championship contention.
Blazers fans would know this well given their team has only had one year where they weren’t the in the NBA’s basement as far as defensive ratings go, be it with CJ or Anfernee as Lillard’s sidekick; the furthest they ever got with either was the Western Conference Finals and the best their defense has even been was 10th. Every other season, the Trailblazers defense has been amongst the worst in the NBA. Part of those Blazers teams' failures can be attributed to bad coaching, but a more significant portion of the blame be laid at the feet of Dame being a bad defender and undersized who has been paired with bad, undersized guards throughout much of his career.
You can get away with one bad defender or a starter who’s undersized for their position on a championship-caliber team which, if you’re rebuilding by trading away Siakam, that is what you’re hoping to take a step back for. As an example, Dirk Nowitzki wasn’t known for being a lockdown defender and yet the Mavericks won their first and only championship to date with Dirk as the weak link on defense. He was also a phenomenal offensive talent whose weaknesses on defense were mitigated by how much momentum he was able to generate for his team but I digress.
You can get away with running several smaller players for a limited time to force mismatches on offense with the right lineup. The Warriors dynasty comes to mind, where Golden State would close games using their “Death Lineup”. However, that lineup revolved around 4 Hall of Famers (Klay, Dray, Steph, Igoudala) where Steph is the lineup’s weakest link on defense, and this is before we acknowledge that they were able to include yet another HoFer in Kevin Durant to replace Harrison Barnes in a different incarnation of the Death Lineup from 2017 onward.
For that matter, it's not wholly impossible to win a championship with a duo of small guards - the Pistons repeated in the 89/90-90/91 with 6'3 Joe Dumars and 6'1 Isiah Thomas and the Bad Boy Pistons were contenders throughout the 90s - but it is damn near impossible if your lead guards are bad defenders. Whatever can be said about Thomas' various off-court controversies, notably with him being found liable for sexual misconduct during his stint heading a woman's basketball team a la the New York Liberty, he was a phenomenal defender, as was Dumars.
Hell, the Raptors won in 2019 while having Fred VanVleet and Kyle Lowry share the floor a fair amount of time in the Finals though it is once again worth noting that both were terrific defenders at the time. Even if one wouldn't call their efforts All-Defense caliber, they were both positives on that end of the floor.
Historically speaking, you cannot be a championship-caliber team with two of your starters being undersized negatives on the defensive end barring them being surrounded by generational defenders or said starters being generational offensive players who can make up for how many points you’re giving up on the other end of the floor.
Simons is a gifted scorer with good playmaking but is a truly sorry defender. Scoot Henderson is a talented passer but is undersized for the position and how he fares defensively with teams hunting him as the smallest player on the court will remain to be seen. But with neither of them likely to be a Dumars/Thomas-level defender and the offensive capabilities for one of them being the main question mark as to how good a player they could become, having both of them as the foundation to your team's backcourt seems to cement the duo's future as a non-contending entity.
Let's put this into perspective with some statistics: Of the past 40 years, the only championship to ever be won by a team with what could be considered a bad regular season defensive rating was the 2000/01 Lakers. That team had two generational talents in Shaq and Kobe, and that season is itself an outlier when compared to the rest of the Shaq/Kobe Lakers era that it shouldn't even count. All other championship teams were at least 12th or higher for their season with most championship teams being in the Top 5 in defensive rating.
By the by, in case you're wondering: That team who had 12th in defensive rating was the 1995 Rockets led by the generational talent in Hakeem Olajuwon and said rating had a lot to do with untimely injuries to the 95 Rockets core. That team they still managed to have the 7th best offensive rating in the league despite Drexler's absence for much of the season is a testament to Future Raptors Retiree Hakeem's skills as the best big man of the late 80s, early-to-mid 90s. Are we noticing a pattern here?
Even if we ignore the question about what to do with Fred, the question of what the Raptors backcourt looks like is far more pertinent if it is going to involve some combination of Scoot Henderson and Anfernee Simons with, presumably, Gary Trent Jr. and another guard coming off the bench for relief. Is a backcourt of Anfernee Simons and Scoot going to turn this team into a Top 3-6 offense for the season without plummeting this team's defense off of a cliff? And if you don't think so, when do you move one of them to open up the 1 or the 2 for another player?
This is a question the team will likely have to answer once they've seen how Simons and Scoot fit togethefit with the rest of the roster; I don't see a 3-team draft day deal where Simons or the 3rd pick are moved elsewhere barring that aforementioned moving down to 4th and I don't see this team without Siakam/with Scoot and Simons being a serious contender for several years even if they do pan out. But it is a question that has me concerned in regards to how this team will function when it's developing a dynamic duo of players who will be picked apart in the playoffs barring one of them turning into a terrific defender.
Whatever else one can say about Point Scottie or even Scottie Barnes when he was crammed into the starting Shooting Guard position for much of the year, it is hard to argue that having either Scottie or Trent & Simons/Scoot as your backcourt makes way more sense defensively even if having both Scottie and Scoot complicates matters on the offensive end since neither are great shooters and Trent's defense is a touch overrated at time due to is propensity to gamble for steals.
All this being said, it's not out of the realm of possibility that Henderson becomes an All-Defense-caliber player or for Simons to a climb out from the deep hole he's dug for himself as one of the worst defenders in the league, and Scoot is still a phenomenal talent. These concerns should be noted, but they shouldn't serve to deter from selecting him 3rd if such a trade were to go down. As a prospect, there's very few players in this draft class who could serve to singlehandedly raise the floor and the ceiling of this team in the long run.
Speaking of other players, however, it should be acknowledged that Scoot isn't the only potentially available player at 3; while all accounts suggest the Hornets prefer Brandon Miller at 3, Scoot is the best player available at 2 and there's no guarantee the Hornets draft for fit. So here's a quick rundown of Miller and a player the Blazers have recently worked out, Amen Thompson:

• Brandon Miller is a 6'9 forward (boo, we have enough of those!) who can shoot (yay, we need more of that!) and has some notable playmaking upside even if his decision-making can be questionable at times. He's a player you could see as either a #1 or a high level #2 option on a championship team though he's not the most switchable guy on defense and you have the usual rookie concerns i.e. "he needs to get the NBA body to thrive". He's gotten a lot of comparisons to Paul George but i'd say his playmaking is further ahead from what PG13 was as a prospect.
• Amen Thompson is someone I talked about in the trade for the 4th pick & he's a very interesting player. A high ceiling, low floor player with unreal athleticism, a 6'7 lead guard who's arguably the best passer in the draft class but has serious questions about the competition he's faced in OverTime Elite/his shooting being as bad as it was. Think Ja Morant but with defense and, again, at 6'7 with a much longer wingspan.

I feel like the trade makes more sense if the Raptors were to go for Amen or Miller but we won't know who the Hornets will chose on draft night until the day of & ideally you'd trade down for 4th to get Thompson plus assets if you're sold on Amen. Plus like I said, it is possible that Scoot does become a good or even great defender so one might not have to worry about choosing between him and Ant down the line.
TL;DR - Scoot is an amazing prospect but his pairing with Simons could be a major problem in the future if both don't improve defensively. Ironically, the 3rd pick becomes simultaneously more valuable for other teams/less valuable for the Raptors if it's Scoot and vice-versa if it's Miller due to those concerns. Thompson is a wildcard at 3 depending on who has the pick/how willing the Rockets are to trade up to 3rd.
Nassir Little
Portland is reluctant to deal out Sharpe. We can debate on whether or not it's fair value for an All-NBA caliber player like Siakam, how much his contract being expiring should affect a deal (we'll ignore the fact that he can be extended by Portland and that any front office making a trade like this should be doing their due diligence by speaking to Pascal Siakam beforehand) or how good Sharpe actually was as a rookie overall instead of solely focusing on that stretch where the Blazers let him do whatever because they were tanking but regardless, the Blazers seem intent on keeping him. Fair enough, Masai is likely aiming for more than Anfernee and 3 - especially for the reasons listed above if it is Scoot Henderson - but Sharpe is likely a hard sell for the front office even if they are going all-in i.e. they want to keep at least one young guy on the roster for the long-term.
That being said, there's still the matter of salary matching, and that's where one of Nassir Little or Sharpe has to come in (They're not going to move Nurkic in the deal for Siakam unless they have something lined up for their center situation i.e. tampering for Naz Reid); the only way for the Blazers to neatly absorb Siakam into their cap with just Simons is by renouncing their rights to Jerami Grant and they need to re-sign him/move him to the 3 (Grant is a really bad rebounder for a PF; the man is a career 4 RPG) if they are serious about competing with Dame.
So...yeah, Nassir Little. Little is what people think O.G. is: A good defender who is often injured, Little is a solid 3 & D wing who, unlike Anunoby, has never played more than 55 games for a given season. Granted, 2019/20 and 2020/21 were shorted to 72 seasons but regardless, injuries have hampered the 23 year-old in the same way that Otto Porter Jr.'s potential was sapped due to a career-long battle with injuries. Still, when considering his age and production, his newest contract ($28M/4 years) is amazing value when he's healthy.
But much like Otto (who I think technically could be sent in such a deal due to the rules around incoming/outgoing salaries), the question of when he's available is a common one. Little is a good young player but one whom you shouldn't get your hopes up about changing the team's direction.
TL;DR - A little salary (sorry) is needed for the deal to happen on draft night & Nassir would be a decent choice for forward depth off the bench. One will have to carefully factor in injury concerns when evaluating the team's depth.
Keon Johnson
So like I said, Sharpe is likely to be ruled out. I debated if I should cover him at all but i'm honestly not sold on Shaedon as a prospect and we've already met the quota for rants with the "Simons/Scoot frontcourt will be exploited" talks. That said, I don't think the Raptors would settle for just Simons and the 3rd pick or the 3rd pick plus assets from a 3rd team were Anfernee moved due to the aforementioned backcourt issues with Simons and Scoot. For now we have Keon Johnson.
Fun fact: When the Raptors were expected to draft 7th in the 2021 draft, Johnson was a common player mocked for the 7th pick.
He wound up going in the 20 to the Clippers (via the Knicks in a trade) who eventually fleeced the Blazers in a deal including him for Norman Powell.
Keon Johnson...hasn't really done a whole lot thus far. He was noted for having an impressive vertical of 48" at the 2021 combine which broke a previous record, he's a terrific athlete and he's about the same age as Scottie so he lines up with a rebuild or retool around Barnes...
...and that's where the positives end. Like I said, Keon hasn't demonstrated all that much on either team he's been on. For a guard, he's not a great ball handler, he isn't a good shooter, he's got decent size and the speed to be a good defender from 1-3 but his potential on that end does not All-Defense caliber. He'd be a throw-in that you'd hope can develop over time, likely spending a lot of time in the G-League because as of right now, he isn't going to be a significant contributor on either end.
TL;DR - Keon is on a rookie deal so you'd be taking a flier on him/betting on your development bringing out the best in him if he were included.
Other pick(s): As far as immediate draft capital goes, the Blazers have the 23rd pick in this draft, which is around the range where players the Raptors have been rumored to be interested in/interviewed (Bilal Couliby, GG Jackson) would likely be available. There's been some speculation that the Blazers could send this pick to the Bulls so they can get their owed pick back from Chicago but nothing concrete has come out regarding whether the Bulls would settle for that vs. hoping the Blazers make the 1st round and lose so they can get a pick in the 16-20 range.
That said, the future pick owed to the Bulls is where things get tricky if the Raptors did want a future 1st: The Blazers pick is protected until 2028. It is technically possible for them to offer a swap in 2029 but without the protections being removed on the Bulls-bound 2024 1st (The 2029 pick cannot be moved due to the Stepien Rule), any future draft capital would need to come in the form of the 2023 trade deadline's currency of choice: Second round picks.
Some of the notable 2nds include:

• A 2024 2nd that could come from the Hornets or Wolves
• A 2028 Warriors 2nd
• This year's second via the Hawks which is 45th
• The Blazers own 2nd in 2028

Not that these are a good substitute for a first-rounder but with the Blazers draft capital being restricted and the CBA's changes to 2nd round contracts, it's better than no future firsts if the 2023 Knicks pick is considered a bridge too far.
TL;DR - There is some interesting draft capital here beyond their own 1sts, especially if the 23rd pick is available in a deep draft like this, but ideally one would want a future 1st from the Blazers rather than a handful of 2nds given Dame's limited window.
Conclusion
I was originally going to talk about the 4th overall pick too but this got a bit lengthy so I made that into a separate post. As far as the 3rd pick package, in some ways it's better than one surrounding the 4th pick because Simons is a flatout better player than any one the Rockets would send back but it's also worse when you factor in Simons or Scoot's respective ceilings vs some of the potential prospects that could come in a 4th pick package?
You're getting significant depth at the guard position if it is Scoot/Simons but there's a huge question mark as to how good the defense will hold up with two undersized guards, one of whom is a bad defender, will hold up in the playoffs.

What would you do in this situation? Do I keep playing the live and wait till my prime acuna is 20/20 or just play the live series always