NBA Trades: Grading 5 Jrue Holiday proposals for the Milwaukee Bucks

Feb 14, 2022; Milwaukee, Wisconsin, USA: Benny Sieu-USA TODAY Sports
Feb 14, 2022; Milwaukee, Wisconsin, USA: Benny Sieu-USA TODAY Sports /
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If the Milwaukee Bucks want to make some very seismic changes to their roster this off-season, one route they could explore is trading Jrue Holiday.

It’s not the likeliest scenario for Milwaukee, but he could undoubtedly bring back a haul, given that he was an All-Star this past season and has a lot left in the tank. Furthermore, no Bucks player on the roster is untouchable, excluding Giannis Antetokounmpo. With that in mind, FanSided’s own Jack Simone put together five Holiday trade packages for the Bucks to consider, and here is a grade for each of them.

Grading a trade proposal between the Milwaukee Bucks and Portland Trail Blazers

At first glance, this trade might puzzle Bucks fans. Why would they trade Holiday, who was named an All-Star for the second time in his career this past season, and Brook Lopez, who just had what many would consider his best season in years, for two young players, a passable center, and a pick that is high, but it not a guaranteed star player? Well, there are a few reasons.

First and foremost, this trade would help the Bucks’ need for youth. It was apparent this last year that Milwaukee’s roster, which was the oldest in the league, could not keep up with young teams, such as the Miami Heat, which the playoffs showcased. Simons (23) and Walker (20) would be a pair of players who would bring some youth to town.

These are not throw-ins either, as Simons has shown legitimate potential as a lethal scorer in this league. He’d be the perfect third fiddle alongside Giannis Antetokounmpo and Khris Middleton on offense. As the past few years have shown, the Bucks’ offense tends to be stagnant at times due to a lack of reliable scorers around those two. Simons would instantly help with that issue. Walker is still incredibly raw, but at 6-foot-9, he would provide some size on the wing and a player with a good amount of upside, something this team does not have much of right now.

Nurkic does not exactly fit with the Bucks as well as Lopez or Bobby Portis, but he could be a fine backup to the latter, who would presumably take on a full-time role as a starter in this situation.

The true prize of this trade would be that third overall pick, given Milwaukee’s desire for youth and just how strong the top three possible picks in this draft class are. Victor Wembanyama will be the first name off the board, but after that, Brandon Miller and Scoot Henderson are the next names. With The Ringer’s Kevin O’Connor reporting that the Charlotte Hornets, who hold the second pick, are likely to take Miller, the Milwaukee Bucks could select Henderson in this scenario.

Henderson, who is 19, would not only add some youth to the roster, but he would be among the best pure athletes this roster has had since Antetokounmpo was drafted. He’s a ball of energy at all times, and he’d be a perfect pairing with Antetokounmpo out in transition, as these two on the break would be must-see. Henderson and Simons would form Milwaukee’s exciting backcourt of the future here and put two tremendous pieces alongside Antetokounmpo and Middleton.

Essentially, the Bucks do this to keep their title-contending window open for as long as possible. Holiday is 32 years old and has said that he will seriously consider retiring when his contract with the Bucks runs out in two years. Lopez is 35, and while he showed that he could still play at a high level this past season, it remains to see how much longer he could keep it up. The young pieces in this trade would give the Bucks a core that still has room to grow rather than one that feels like it is ticking toward the end. Yet, it’s still not a perfect deal, as there could be some growing pains with those young pieces, which could lower the Milwaukee Bucks’ ceiling in the short term.

If the Blazers were to do this, it would be to put this team in a position to contend immediately. Damian Lillard has made it clear that he wants this team to get win-now pieces rather than just focus on building for the future. Adding an All-Star guard and 2023 Defensive Player of the Year runner-up would undeniably fit the billing there.

BTBP Grade: B+