Milwaukee Bucks: Will Donte DiVincenzo and Grayson Allen get extended?

Much of the discourse surrounding the Milwaukee Bucks this past offseason has revolved around the shooting guard position.

The fanbase has gone back and forth as to whether Donte DiVincenzo or Grayson Allen should be Milwaukee’s starting two-guard for 2021-22. It is a compelling topic that has no clear-cut answer at the moment and should help conjure some competition between the two young guards with training camp set to officially begin next week. Interestingly enough, both DiVincenzo and Allen are set to hit restricted free agency after the season, which should add another layer to this ordeal as the two look to prove their place.

Of course, the Bucks could look to jumpstart the process and get both players signed to their rookie-scale extensions before the October 18 deadline. This is something that general manager Jon Horst has thought about, as he discussed in a recent sit down with The Atheltic’s Eric Nehm (subscription required). When Nehm asked Horst about the possibility of getting both players signed on, the former Executive of the Year highlighted how having those discussions is a priority and that the two sides will look to navigate toward a deal, but that he does not view it as a move that is absolutely necessary. Considering both players have some question marks, it makes sense.

Will Donte DiVincenzo or Grayson Allen receive rookie extensions with the Milwaukee Bucks before the deadline?

While the discussions will likely go on until the deadline, the Bucks should be fine with taking a patient approach in the negotiations.

That should particularly be the case with DiVincenzo, who is coming off a season-ending injury in June. Horst noted that DiVincenzo looks great in the rehab process, which is welcoming news. Yet, there should still be some concerns as this was his second season-ending surgery in his three NBA seasons. To his credit, he put up career-highs practically all across the board last year in his first full season as a starter, but this injury has clouded his stock at the moment. The team would be wise to wait it out and see how DiVincenzo looks when he returns from the injury before giving him a nice raise.

As for Allen, he is yet to suit up for the Bucks after Horst traded for him in the offseason. While the guard seems destined for big things in Milwaukee, that is all speculation at the moment. The front office would likely want to get a better look at the 25-year-old before committing to him for the long haul. With DiVincenzo’s return uncertain as he works his way back from surgery, Allen seems to be the favorite to start for the Bucks at shooting guard to begin next season, and getting a good look at him in that role would be smart.

All in all, who knows if either player will get extended before the deadline. It would certainly be interesting to see one get a new deal but not the other, whichever way that would be. However, the likeliest scenario is that both players enter the season without new deals so that the team can get a better evaluation of where they both stand at this moment.

Only time will tell, and be sure to keep an eye out for that October 18 deadline.