If I had to answer the question in the headline with one word: No. However, whether the Milwaukee Bucks should trade Jrue Holiday is highly debated this offseason and deserves further scrutiny.

The Bucks are coming off a disappointing playoff “run” that prematurely ended after a gentleman’s sweep in the first round. It was the most surprising result in a postseason full of them. It directly led to the firing of head coach Mike Budenholzer.

As Milwaukee works to fill their head coach position, other questions exist about the roster. Will they make dramatic changes after falling short of the NBA Finals for a second consecutive year?

If the answer to that question is yes, the only realistic path they have to upset the balance is to trade away some of the top players on their team. I highly doubt they’ll entertain a trade involving Holiday, but wilder things have happened.

For starters, the Bucks would need to find the right type of trade partner. A rebuilding team isn’t going to want the 32-year-old Holiday, who will likely contribute to far too many regular season victories than they would like.

Focusing only on contenders eliminates at least half of the NBA. Suppose I’m being generous with my definition of teams who want to win now. In that case, that leaves 18 possibilities: the Atlanta Hawks, Boston Celtics, Cleveland Cavaliers, Dallas Mavericks, Denver Nuggets, Golden State Warriors, Los Angeles Lakers, Los Angeles Clippers, Miami Heat, Minnesota Timberwolves, New Orleans Pelicans, New York Knicks, Philadelphia 76ers, Phoenix Suns, Portland Trail Blazers and the Sacramento Kings.

Given the narrow scope of the NBA’s trade rules, the Bucks couldn’t acquire more than 110 percent of outgoing salaries. If they only trade Holiday in a deal (he’s set to earn $36.86 million in 2023-25), they wouldn’t be able to acquire more than $40.55 million in a deal. The same would be true for a team acquiring Holiday.

Before Milwaukee seriously considers trading Holiday, they must determine their goal this offseason. Suppose it’s to reload around Giannis Antetokounmpo, get a bit younger and build for the future. In that case, trading Holiday might be the tricky but accurate route.

It would still be very difficult to find the right pieces to trade Holiday for (see the potential deals below), but it could be worth exploring.

Keeping Holiday is the clear path forward if they want to win now and give themselves the best chance to bring home another Larry O’B. He has two years remaining on his contract (including a player option in the final year) and has discussed retiring at the end of this contract. However, he still has plenty left in the tank as one of the best offensive/defensive guards in the NBA. There won’t be an upgrade available via the trade market.

Working off the list of 18 contenders from above, I’m eliminating the following teams due to an unrealistic path toward a trade: Cavaliers, Mavericks, Nuggets, Clippers, Lakers, Timberwolves, Pelicans, 76ers, Suns, Kings . This unrealistic path could be due to incompatible salaries in a potential deal, requiring a sign-and-trade that would hard-cap the teams, the other team being set in the backcourt, or other reasons.

Before we move on, I want to be clear I’m not endorsing any of these trades. his exercise aims to give you an idea of what a potential trade involving Holiday would net Milwaukee.

Bucks trade Jrue Holiday and MarJon Beauchamp to Hawks for Dejounte Murray, Onyeka Okongwu and Saddiq Bey: Atlanta triples down on the Trae Young era by acquiring a rich-man’s version of Murray. Milwaukee gets a young up-and-coming center, a wing defender, and a feisty combo guard. The additions of Beauchamp and Bey were needed for salary-matching purposes.

Bucks trade Jrue Holiday to Celtics for Jaylen Brown: This one-for-one swap works within the salary cap rules and would be a major shakeup for two Eastern Conference contenders. Milwaukee gets a younger player to pair with Antetokounmpo on the wing, while Boston gets an elite defender who can fit perfectly into their switchable lineups.

Bucks trade Jrue Holiday to Warriors for Jordan Poole, Jonathan Kuminga and Moses Moody: Lol.

Bucks trade Jrue Holiday to Grizzlies for Steven Adams, Tyus Jones and Desmond Bane: Milwaukee acquires a true point guard and starting-caliber player in Tyus Jones, while also adding a big man on a good contract and a wing defender. Memphis gets Holiday to pair with Ja Morant in the backcourt and push their timeline ahead.

Bucks trade Jrue Holiday to Heat for Tyler Herro and Caleb Martin: Miami gets another star to pair with Jimmy Butler and Bam Adebayo, while the Bucks add a young playmaker in Herro and wing depth.

Bucks trade Jrue Holiday to Knicks for RJ Barrett, Josh Hart, and Immanuel Quickley: This move eats at the Knicks’ depth on the wing, but gives them a star who pairs perfectly with Jalen Brunson in the backcourt. Holiday can easily assume the role of the primary wing defender, allowing the Knicks to keep Brunson hidden on defense. Milwaukee loses talent at the top of their depth chart, but gets some younger contributors who could take another leap.

Bucks trade Jrue Holiday to Trail Blazers for Anfernee Simons and 3rd overall pick: This would have to be completed after the third pick is signed for salary-matching purposes. It would give Portland the star to pair alongside Damian Lillard they’ve been searching for. Milwaukee would acquire a 23-years-old score-first guard and potentially Scoot Henderson. It would cost the Bucks in the short term but could have long-term effects that extend their championship window with Antetokounmpo.

I can’t believe I did that. I tried to touch on deals across the spectrum: Ones that included a player-for-player swap, some that had Milwaukee acquiring a plethora of players, and even a deal that attached a top draft pick.

Milwaukee’s goal should be to maximize these next two years with Antetokounmpo at the helm. To do so, they should keep Holiday and retain most of their talent from last season’s team, hoping a coaching change will spark the fire they need.