The one example in which we have of a team going through the entire cycle of acquiring multiple draft picks and seeing them through is Boston. In 2013, they acquired a package featuring three unprotected first-round picks and a pick swap from the Nets for a group of veterans mainly featuring Kevin Garnett and Paul Pierce.
This deal could be identified as the original ‘all-in’ trade involving multiple unprotected first-round picks in the modern era. At the time, no such comparable trade involving that many future unprotected picks had been consummated since the implementation of the Stepien rule. The Nets arguably experienced the worst-case scenario in this deal having given up a 1st overall, 3rd overall (swapped for 27th overall), 8th overall, and 17th overall selections while only winning one playoff series. The core quickly disappeared as the Nets decided to pivot to a rebuild and save money after making enormous luxury tax payments.
The Celtics had an embarrassment of riches not only from this deal but also from deconstructing their roster between 2013-2015. They drafted Jayson Tatum and Jaylen Brown using picks from the Nets trade, which alone made the deal work out for them. This allowed them to both be in a rebuild while being competitive at the same time. Since drafting Brown and Tatum, the Celtics have made three Eastern Conference Finals appearances in five years, including one trip to the Finals. They remain a heavy favorite to win the championship this season.