By my count, Jerry Jones and the Cowboys have engineered 84 trades involving draft picks since 1989. Some of those trades, like the franchise-defining Hershel Walker trade in 1989, were hugely successful, while others, like the acquisition of wide receiver Roy Williams, were unmitigated disasters.
Since 1989, the team have been involved in draft day trades in 28 of their 32 drafts under Jerry Jones. The only four years in which the Cowboys managed to keep their feet completely still on draft weekend were 2000, 2011, 2016, and 2018, when they did not move away from their originally assigned draft spots once over the entire draft weekend.