It's been a turbulent offseason for the Milwaukee Bucks, to say the least. The crazy thing is, even if it is nearly October, more moves might be coming that could pile on the change before the team's first regular season without Giannis Antetokounmpo in a long time. With that said, let's break down several storylines that could still alter Milwaukee's offseason.
Gary Trent Jr. investigation
The NBA continues to investigate whether or not the Bucks circumvented the cap by re-signing Gary Trent Jr. to a hefty new deal this summer despite his poor play. If Milwaukee did indeed promise their guard a lofty new contract ahead of time, as many speculate, their rebuild could hit a snag just as it's in its early stages.
Per The Athletic's Joe Vardon (subscription required), if the Milwaukee Bucks are caught red-handed, their punishment could match or exceed what the LA Clippers got handed in their cap circumvention case. Losing multiple first-round picks and being fined a significant amount would be devastating for the Bucks after trading their former star. For now, all they can do is wait for a verdict.
Jalen Duren pursuit
Just when it felt like the Milwaukee Bucks were content with their roster, The Athletic dropped a story reporting the contrary. Per Sam Amick and Hunter Patterson (subscription required), the Bucks have a serious interest in acquiring Detroit Pistons restricted free agent Jalen Duren. With training camp on the horizon, Milwaukee could be eyeing a splash.
Duren would make plenty of sense with this new group. While Myles Turner already looks like a great veteran for this young group, Duren is eight years younger and was just an All-Star. Just about every single team would swap the two if they could. The question is whether the Pistons would actually be willing to trade him and if the Bucks were fine with parting with quality assets to get him.
Lingering roster tweaks
Teams are allowed to carry 15 players on their standard roster and three extra via two-way contracts during the NBA's regular season. As things stand, Milwaukee has 17 standard players and two players on two-way deals, leaving the door open for more movement with less than a month to go before the regular season begins.
With training camp nearing, everyone will have an opportunity to prove themselves. There are so many fresh faces in Milwaukee, including Taylor Jenkins, so the team wants to get a good look at who fits where before making any decisions. In terms of adding players, the Bucks could snag another body on a two-way if someone desirable gets cut due to a roster cutdown elsewhere.
Possible extensions talks
Earlier this offseason, a Bucks executive told Spotrac's Keith Smith that the team would "love" to get deals done with Tyler Herro and/or Jaime Jaquez Jr. before the season if it made sense. Considering that was in July, it feels safe to say that neither will be getting new deals, but there is always a chance the sides could come to an agreement before the new season.
While inking a new deal with the Milwaukee Bucks could take a weight off the shoulders of Herro and Jaquez, it could also create regret in the long term. Both are primed to have the most prominent roles of their careers and could put up career-defining numbers. If they sign the extension later, it could be far richer than anything on the table right now. It could happen now, but it's unlikely.
Stay tuned for more Milwaukee Bucks analysis.
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