No. 5 – The Grayson Allen trade
For years, the Milwaukee Bucks constantly cycled through names at the starting shooting guard position. Donte DiVincenzo had been the starter for all of 2020-21 before an ankle injury knocked him out of the NBA Playoffs. As DiVincenzo recovered, the Bucks swung a trade for another young contender to take the reigns at the starting two guard, Grayson Allen.
The Bucks acquired Allen and cash from the Memphis Grizzlies in exchange for guard Sam Merrill and two second round picks. It was immediately viewed as a nice move for the Bucks due to their need for depth in DiVincenzo’s absence, which carried over deep into the season. Allen was an immediate upgrade over Merrill, who scarcely played in his rookie season the year prior.
Shortly after getting off the plane, Allen became Milwaukee’s starting two-guard. Playing a major role as a full-time starter for the first time in his career, Allen took advantage of the opportunity and put up the best numbers of his NBA tenure in several categories. He primarily made his mark as an outside shooter, hitting 40.4 percent of his triples over the past two years with the Bucks.
To be clear, the Allen acquisition wasn’t a home run for Milwaukee, as the guard has had his share of struggles, particularly in the 2022 Eastern Conference Semifinals. However, it’s hard to deny how good of a move this was for the Bucks, having flipped a second round pick who was never going to see prominent time into a full-time starting shooting guard.
The Allen trade recently just helped the Bucks land another player, and that trade will be featured near the top of this list.