Every owner/GM needs to gamble for a team to succeed. Hindsight is always 20/20, but the truth is that every transaction is a risky move until proven worth. Freak accidents, team chemistry issues, etc are all factors you can’t measure before a trade/signing. Off the top of my head, rookie Kobe for Vlade was one of the biggest payoffs in NBA history (as for “riskiest” move, that is up for debate)
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Warriors trading Ellis instead of Curry. One hell of a payoff I’d say
Trading Pau for the rights to Marc Gasol like 2 years before he was eligible for the NBA. Might be wrong at that but look at his senior year pic at Lausanne and tell me the Grizz FO didn’t take an insane shot and it worked out.
That’s where this question gets tough. As revisionist history creeps in.
Kobe for Vlade as one of the dumbest trades of all-time retroactively, but the Lakers obviously knew Shaq was going to sign with them, so they traded a big for the 13th overall pick (a prospect they really liked!)
And, even though they knew Shaq was going to sign with them, they couldn’t have financially done it without moving Vlade.
Shaq for Vlade seems like an LA win. Before even throwing in Kobe.
No actual risk involved.
Easily the Raps trade for Kawhi in '19
Acquiring Kawhi Leonard on his last best year for demar and jakob.
Gave up being a good team to be a great team.
Won a championship.
Pistons going for Sheed despite of his JailBlazers reputation.
Nuggets trading up to draft MPJ
Nuggets didn’t trade up. They had the 14th pick - last pick of the lottery - due to losing their last regular season game against the Timberwolves.
He was barely a lottery pick when he had #1 talent, wasn’t much of a risk.
Mavs trading young star point guard Devin Harris for an aging Jason Kidd in a pretty desperate gamble for the title. It was a trade pretty roundly criticized at the time.
That Kidd/Dirk title team was great. Defeating the Heat must have been even sweeter.
NO ONE thinks of this, but the Mavs traded two first round lottery picks to move up two slots in the draft to get Luka. Luka had some buzz, but I don’t think he had “two first round lottery picks for him” buzz by anyone.
I’m not a Mavs or Hawks fan, but how do you say “NO ONE” thinks about that trade?!?
I think about it about every time I see Trae Young’s name. The Hawks really traded Luka for Young.
Why are you phrasing this so strangely? The Mavs gave up a top 5 protected first to move into the top 3.
Rockets trading for Clyde Drexler at the 1995 deadline.
Common practice is to run it back with a Championship team aiming to repeat. For instance, the Mavericks infamously giving up Tyson Chandler in a sign and trade. The Rockets traded away their starting PF a former 1992 All Star Otis Thorpe. They would have to use Horry as a stretch 4 and rely more on Carl Herrera against bigger front courts.
In the Chemistry front, the Rockets would only have half a season to incorporate Drexler into their system. The Rockets went 15-18 to end the regular season when they had been 32-17 before the trade. The Rockets finished as the 6th seed and would have to face the Top 4 teams in the NBA en route to a championship.
The trade also led to another key member of the defending champions departing. Vernon Maxwell became unhappy with his reduced role, lashed out and left the team during their 1st round series against the Jazz.
The end of the regular season plus falling behind 3-1 against the Suns in the 2nd round left many questioning the Drexler trade. Of course, The Rockets won 3 straight against Phoenix, Olajuwon put on a clinic against the MVP David Robinson, and swept the Magic in the finals.
I was going to post about this as well, so just a quick correction: They were 29-17 prior to the trade, played one game without Thorpe or Drexler, and then finished 17-18 once Drexler joined.
2004 pistons trading for Sheed which then help them getting 4-1 against ultra favorite Lakers in finals
And on the other side, a risky move that didn’t pay off… drafting Darko #2, ahead of Carmelo (who was considered the consensus #2 pick, having just dominated in the NCAA tourny as a freshman).
And not only him, but also taking him over the next two picks - Chris Bosh and D.Wade.
Were Bosh and Wade even in the conversation for top-3? From what I’ve read, the consensus was LeBron, Darko, and Carmelo. There was even a story that Darko had a great workout session and was hitting great shots while members of the Pistons were watching
Darko is one of the greatest “don’t draft based on position if you have a top-5 pick” examples in NBA history.
Wade and Bosh are more revisionist history (though obviously had HOF careers), but passing up Melo?
Pistons left a lot of money on the table.
We don’t know the payoff yet, but trading Marcus Smarf was pretty ballsy