Why the Bucks should do it
Milwaukee can win. In the lackluster Eastern Conference that saw many of its main superstars venture out West, Milwaukee might be able to find their spot right now if they can get the right pieces.
All they really need to do is acquire enough assets and scorers to challenge the Cavaliers. While Giannis is in the process of budding into one of the NBA’s best players, he will need more help. Middleton is a fantastic sharpshooter, but Kevin Love could certainly help Giannas more with his size. Love is also a great shooter, averaging 0.4 more threes per game than Middleton last season. Courtney Lee could also supplement the outside shooting lost by Middleton, and Shumpert could help bolster their bench depth. A second unit backcourt of Delladova and Shumpert would be dominant defensively, especially since they are already familiar with each other from their Cleveland days.
The Bucks would also lose some youth in Vaughn, a young wing that proved to be a dynamic scorer in the summer league. Vaughn only averaged 11.2 minutes per game last season, so if Milwaukee is truly committed to winning now, they might deal both him and Middleton. Monroe is less of an issue since they would be acquiring an equally impressive rebounding big in Love.
If the trade could lock Milwaukee in as a threat in the Eastern Conference, why not do it? While they have a good team right now, a trade like this could truly make Milwaukee a Finals’ contender.