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Celtics could look to recreate their Jrue Holiday magic in Giannis sweepstakes

They wouldn't get Antetokounmpo, but they would have the rare opportunity to get someone who would help!
Mar 24, 2025; Phoenix, Arizona, USA; Milwaukee Bucks forward Giannis Antetokounmpo (34) celebrates a play against the Phoenix Suns at Footprint Center. Mandatory Credit: Mark J. Rebilas-Imagn Images
Mar 24, 2025; Phoenix, Arizona, USA; Milwaukee Bucks forward Giannis Antetokounmpo (34) celebrates a play against the Phoenix Suns at Footprint Center. Mandatory Credit: Mark J. Rebilas-Imagn Images | Mark J. Rebilas-Imagn Images

All of the whispers about Giannis Antetokounmpo indicate that he has interest in joining the Boston Celtics, but the feeling might not be mutual (?). Further whispers indicate that his next team will be the Miami Heat. Because Milwaukee would trade Antetokounmpo with the hopes of rebuilding, Boston could get in on the deal by prying Tyler Herro from it.

Whenever Brad Stevens has gotten the chance to add a game-changer, he has taken it without thinking twice. That has included when teams trade their valuable guys for upgrades. Once Milwaukee traded old friend Jrue Holiday, Stevens immediately pounced on it. Stevens might not be interested in the Greek Freak, but he has the chance to make another Holiday-like situation come to fruition again: this time getting Herro.

The Celtics should be on the prowl for more help this offseason. Maybe they're not looking for an upgrade, but want a game-changer to put next to Jayson Tatum and Jaylen Brown. More importantly, they would want it at the lowest possible price. Ergo, Herro.

Miami will have to include him to make the contracts work, and his value couldn't be cheaper at the moment because it is set to expire in 2027. The chance to get someone who can put up 20 points on any given night while also perhaps having the inside track to getting him signed to a team-friendly deal?

Boston could do worse...

Herro wouldn't necessarily be the best player to put next to the Jays at this juncture, but he might be the most realistic? He is a lethal scorer whose efforts led to the Heat making two surprise run to the finals (I know Celtics fans, the PTSD just triggered in me too).

With the amount of gravity the Jays both possess, Boston would have a safety valve in Herro. He definitely has his flaws on the defensive side, but that didn't certainly prove to be too detrimental in the Heat's championship efforts.

If Boston can make it work with Anfernee Simons, they can do the same in Herro, who is basically the taller version with some winning experience to his name,

The Celtics wanted Herro back in 2019

(Apologies again for any Vietnam flashbacks, Celtics Nation)

Many know full well that Boston wanted Herro ahead of the 2019 NBA Draft and likely would have gotten their hands on him if they had won their coin flip against Miami. That led to Romeo Langford, who led to Derrick White, so long-term, it wasn't the worst outcome, but the fact remains that Boston wanted the player who would play into one of their fiercest rivals of the decade.

Again, Boston has had success with player with similar archetypes as Herro under Joe Mazzulla, like Simons and Malcolm Brogdon. If Herro is their third banana in the pecking order, that makes Boston's offense so much more lethal.

A devil's advocate would say that Boston already has that in Payton Pritchard, and that's fair. Pritchard is pretty fantastic, but imagine a quartet of the Jays, Pritchard, and Herro all working off each other? The Celtics aren't in desperate need of another scorer, but want to be among the elites again. Having another dynamic scorer would help them with that.

Sure, something like this would only come to fruition if Giannis goes to South Beach, but Herro joining the Celtics because of it could be like when Jrue Holiday became a Celtic after the Bucks traded him to the Trail Blazers for Damian Lillard.

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