NBA Trade Deadline 2020: 5 trades to help the rich get richer

3. Bucking the trend

Pelicans also receive G Sterling Brown, 2020 first-round pick (via Pacers), 2021 second-round pick (via Pacers)

There’s a strong argument to be made that the Milwaukee Bucks should be silent at the NBA trade deadline. With the best record in the NBA and a stranglehold on the Eastern Conference, it’s hard to find a more convincing contender right now than the Bucks with Giannis Antetokounmpo, who’s leading the charge with another MVP-caliber season.

Even so, the Bucks had high expectations entering the playoffs last year and were ultimately bounced by the eventual-champion Toronto Raptors in the Eastern Conference Finals. And though the Raptors deserve all the credit in the world for that, it’s hard for fans to shake the memories of how bad Eric Bledsoe was in that series and think that they couldn’t stand to upgrade.

Sure, it wouldn’t necessarily be difficult to take a step up from the 29.4 percent shooting performance Bledsoe posted in the conference finals. However, if the Bucks are going to upgrade, they are going to need to take a big swing at a player like Jrue Holiday with the New Orleans Pelicans.

The biggest possible hindrance to a deal for Holiday (or any high-profile guard that might be available), though, is the Milwaukee front office. They were unwilling to dip into the luxury tax to pay Malcolm Brogdon this past offseason, which means they would have to change their tune if they were to go after a player like Holiday.

But say that the front office did have a change of heart and was willing to go all-in, then Holiday would be the perfect upgrade. Younger than Bledsoe at 29 years old, Holiday offers more consistency and versatility for the Bucks offense while not losing much (if anything) in terms of perimeter defense. Simply put, if you thought Milwaukee was scary now, they’d be terrifying with Holiday at the point.