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)
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.