What now for Celtics after missing out on Jrue Holiday?

(Stacy Revere/Getty Images)

The Celtics’ interest in Jrue Holiday was very real in the past week according to multiple league sources but packaging three first round picks from 2020 was not enough to top Boston’s Eastern Conference rival on Monday night. The Bucks were determined to upgrade their roster around Giannis Antetokounmpo to lower the risk of losing him in free agency next summer so they mortgaged a great deal of their future for the present with a pair of deals.

A look at what they gave up for Jrue Holiday first

  • Three unprotected first round picks (including No. 20 in 2020 NBA Draft)
  • Two future first round pick swaps
  • George Hill (2 years, $20 million remaining on contract)
  • Eric Bledsoe (3 years, $54 million remaining on contract)

Holiday is only signed to a guaranteed contract for one more season (he has a player option for 2021-22) so giving up this big of a trade package for a guy who could walk away in one season is a momentous risk for Milwaukee. On the other hand, the Bucks’ long-term trajectory is a disaster anyway with Antetokounmpo walks away so risking the future now in order to increase your odds of saving him is a reasonable path for the Bucks.

If anything, the Celtics may have driven up the price higher for the Bucks with Pelicans GM David Griffin being able to squeeze everything he can out of Milwaukee from a value standpoint against the threat of Boston’s offering up a top-10 pick in the present.

Ultimately though, this was an offer the Celtics shouldn’t have topped from Milwaukee. There were machinations where a three-team deal could have come together if Gordon Hayward opted in and the Celtics packaged all of their first-round picks but that would have involved a third cooperator which clearly did not materialize. The Pelicans also likely preferred the long-term upside of unprotected picks from Milwaukee instead of a lottery pick or three lower first-round picks from Boston this season.

The Bucks also doubled down on winning in the present by also nabbing Bogdan Bogdanovic from the Kings in what will be a prearranged sign-and-trade in exchange for Donte DiVincenzo, DJ Wilson and Ersan Ilyasova. Whether or not this deal goes through after such blatant tampering remains to be seen but odds are the NBA looks the other way.

The move leaves the Bucks with a projected starting five of Holiday, Bogdanovic, Middleton, Giannis and Brook Lopez, a formidable upgrade to that group in place of what ended up being a lackluster group of role players last postseason.

The question now for the Celtics is what is left for them out there on the trade and free agency market to help try to keep pace for