To answer the OP:The only way this goes down as the worst trades in NBA history is if the pick becomes an MVP caliber player.
I hope so or this deal will go down as one of the worst trades in NBA history and that's not hyperbole.
I think you underestimate the risk.
If Kyrie leaves after two years and we haven't won a title the deal is a massive bust no matter who is selected in the draft. It's not just the pick, it's also Zizic (who was valued as a late lottery pick at draft time), Crowder (one of the best contracts in the league) and breaking up the core of an ascending, 53 win, ECF team. The only way that isn't true is if IT is done (and he's not).
It's also not just "the pick" but the value of the pick. There's a simple economic idea called opportunity cost. Even if the pick turns out to be a bust, there's also the question of who else could we have reasonably drafted with that pick or who we could have received in a trade for that pick. Thus Irving leaving means we gave away a good prospect, a top contract, an All-Star who wasn't yet 30 and a pick that could have returned any number of All-Star caliber players. That's an epic bust any way you slice it.
If it turns out to be #1, Bags ends up being the Next Great Thing and Irving leaves? Then this goes down as the worst trade in modern NBA history. Even worse than the Brooklyn deal that gave us those picks. It would be considered about as bad as the deal that ultimately ended up bringing Magic to the Lakers.
I'm not saying that's what it will go down as. I hope that Irving develops into what we all hope he can become and the Nets pick ends up being 7th or 8th. Then we win. But Lordy there's a lot of risk in this one.
So the BKN trade that brought us:
The #17 in 2014, #3 in 2016, #3 in 2017, the LAL/Sac pick, and the BKN 2018 pick would be worse than trading:
One those picks, an injured/aging star, a good role player, and low ceiling 1st for a perennial all-star in his prime...for at least 2 seasons? I mean, I don't know what to say. BKN got 1 year of Pierce and 1 1/2 years of KG. That is just dreadful and has set that team back for over a decade.
Sticking with recent Boston trades, I would say the IT PHX deal would still be considered worse than this one. Continuing with this exercise, how did Minny really make out in the KG trade?
You typically make insightful, articulate posts on CB, but this one is literally the definition of hyperbole.
Don't bother...he is tripping.
There is really no way this trade could possibly become "one of the worst trades in NBA history" unless multiple events happen that are unlikely and completely unpredictable - for example, if two or more of the following happens:
1. Isaiah somehow recovers sooner then expected, puts up numeers just as dominant as last year and does so for the next 3-4
2. Cleveland trades Kevin Love and the Brooklyn 1st to the Pelicans for Anthony Davis
3. Cleveland, led by the amazing core of IT4/Crowder/Lebron/AD/TT defeat Golden State in the finals and Lebron gets his 4th ring
4. Lebron agrees to sign a super-max deal to remain in Cleveland for the next 5 years and remainder of his career
5. Cleveland goes on to forge a dynasty, winning championships in three of the next 5 seasons - Lebron retires with championship rings, overtaking Jordan and truly cementing his place on Jordan's level as a GOAT candidate
6. Kyrie (knock on wood) suffers constant injury issues with his feet/ankles/knees, never plays more than 50 game in a season for the next 2 seasons, and struggles to match the numbers he's been putting up in previous seasons - injuries also worsen his defence, which now drops off to "worst defender of all time" level
7. Hayward proves that his big season with Utah was purely a result of it being a contract year (and him being extra motivated) - goes on to drop back down to 18-19 PPG - 19 PPG over the duration of his time in Boston. Also goes on to prove that his apparent defensive improvements were only a result of him having Rudy Gobert covering his butt the last couple of years - defence takes a massive decline in Boston and he is exposed as being one of the worst defensive wings in the NBA
8. Al Horford declines again for the 3rd straight season, only this time the decline is far more severe. His numbers drop down to 10 points, 5 rebounds and 4 assists (in 29 MPG) with his percentages dropping to 43% / 29% / 75% - his mobility reduces significantly compared to last year, to the point where he struggles to switch on to power forwards and proves too slow to defend the P&R, with his overall defence reducing to just average.
9. Marcus Morris and his brother lose their lawsuit - both brothers end up gong to jail for several years for aggravated assault, and Morris' never gets to put on a Celtics Jersey
10. Jaylen Brown struggles to prove he is skilled enough to realise the potential people believe he has - after Ainge gives him a max extension, he ends up peaking as a slightly inferior version of Jae Crowder
11. Tatum disappoints - Ends up a weak defensive player who is too slow laterally to guards quick small forwards (or guards) and too weak in the lower body to guard strong small forwards (or PFs) - proves to only be able to defend fairly slow and weak small forwards with relative effectiveness. Rebounds poorly. Jumpshot disappears once he gets to the NBA level due to his struggles against the speed and length/strength of NBA opponents. Ends up proving too soft emotionally to deal with this, and hence peaks as a less athletic Jeff Green.
12. Marcus Smart gets signed to $15Mx4 - goes on to display one of the worst 3-5 year shooting spans ever recorded for an NBA guard, cements his reputation as one of the worst shooters ever to play the guard position in the NBA. Puts on weight due to Sully-like eating habits, develops the body of Raymond Felton and becomes too slow to defend NBA guards. NBA introduces a new rule in which players start to receive a technical foul for every flopping attempt. Marcus Smart ends up leading the NBA in technical fouls for 5 consecutive seasons. After his contract ends no NBA team signs him due to his flopping problems and inability to shoot the ball, so he leaves the NBA and builds a long and successfully career in Russia - where he goes on to thrive off his physicality and flopping skills.
13. Danny trades Terry Rozier (and the Lakers pick) to the 76ers for JJ Reddick - who then has a career ending injury after coming down on Zaza Pachilia's foot on a three point shot. After being given a starting role / minutes in Philly Rozier goes on to become an elite two-way PG, going on to average averaging 22 / 8 / 5 and making multiple all defensive teams. Fultz becomes an elite scorer at over 28 PPG. Rozier and Fultz combine to form one of the most dominant backcourts in NBA history while Embiid heals properly from his injury and becomes the best big man since Shaq. Simmons goes on to become the first player in NBA history to average a triple double 5 straight seasons - Philly meet Cleveland in the ECT for the next 4-5 years, with those two teams proving so dominant that nobody else comes close to sniffing a an ECF run
14. Danny Ainge gets fired, Brad Stevens leaves when his contract runs out (goes to Cleveland because he wanted to be reunited with Isaiah). The trade hurts Boston so much that the team gets sold - gets bought by some big offshore company who decides to relocate from Boston to Maine and merges the Celtics and Redclaws into a new team called the Celclaws - this kills all brand awareness, and the team goes on to become who suck horribly for the next 30 years.
If at least 2 or 3 things on that list occur, then maybe we find outselves in a place where we could make an argument (Knock on wood - I mean I'm actually knocking on wood now) that this could end up one of the worst trades in NBA History.
Failing that, the worst that we are likely to see from this is a trade where we gave up multiple assets (Crowder, Zizic and a good pick) in order to do a trade that ultimately proves to be a side-step. Even then the facts that Thomas is injured and Kyrie is younger still provides justification enough to make the trade worthwhile, and as a result there is realistically almost zero chance that this ever becomes "one of the worst trades in NBA history".