Should the Celtics make a serious run at trading for Jrue Holiday?

(Jonathan Bachman/Getty Images)

The Celtics' front office should be entering this offseason with an aggressive mentality after coming within two games of the NBA Finals this fall. With Jayson Tatum still underpaid on his rookie deal for one more season and three first-round draft picks in pocket, the Celtics have the flexibility and trade ammo to get into most trade conversations for big names around the league, if they desire.

While there is not expected to be any top-tier talent available on the market when trading kicks off again next week, the first All-Star level name that is being shopped emerged on Sunday as Shams Charania of Stadium reports the Pelicans are having trade discussions about combo guard Jrue Holiday with several contenders.

The Pelicans moving on from Holiday makes plenty of sense for where they are as a franchise. Holiday is 30 years old and the rest of the team’s top talent outside of JJ Redick is under 24 years old. After failing to make the playoffs out West last season, it’s evident they are a couple of years away from being a factor in the Western Conference and Holiday could walk out the door as soon as next offseason if he declines his player option.

With a weak free agent class in place for 2020, few teams with any real spending power and several franchises that likely feel like they are one move away from contending next season, making Holiday available now is a wise move for Pelicans GM David Griffin.

So the bigger question when it pertains to the Celtics is whether they should be one of those contenders making a serious push for Holiday. Let’s take a closer look at the 30-year-old guard, what it might take to get him and whether he’s worth the gamble for Boston.


AGE: 30

2019-20 Stats: 19.1 PPG, 4.8 RPG, 6.7 APG, 1.6 SPG, 0.8 BPG, 3.0 TPG, 45.5% FG, 35.3% 3pt, 70% FT (67 games)

Note: Most of these shooting numbers fall in line with his career stats, except for his free throw shooting (77 percent).


2020-21: $26.1 million
2021-22: $27 million (player option)

Overview: The fact that Holiday could be on an expiring contract this season (if he opts out next summer) will limit his value to a degree on the open market. It’s possible that he stays put and opts in if he has a down year or if the salary cap stays low enough for 2021-22 where another comparable payday isn’t available yet on the open market in 2021. The possibility could also emerge of a opt-out and an extension in Holiday’s new home next summer but as the Celtics have seen with Al Horford and (potentially) Gordon Hayward the past couple of years, that’s never a guarantee with player options.


Great defender: The gritty guard has been named to the All-Defensive team twice in the past three years and has been established as one of the best combo guard defenders in the NBA for much of the past decade. He’s quick enough to stick with true point guards off the dribble and can also fight through screens and chase around shooters. That type of versatility is in high demand in today’s NBA and pairing him up with Marcus Smart would easily give the Celtics the best defensive backcourt in the NBA.

Capable secondary playmaker: Holiday has never been good enough to be a top dog for a good offense but he brings a nice blend of scoring and passing as a ball handler. He can get to the rim with ease against most defenders and is a solid finisher for his size (an area that’s improved throughout his career). Even though he averaged 19 points per game last year, he’s a very willing passer who would be fully capable of setting up more shoot-first options like Jayson Tatum or Kemba Walker within an offense.

Win-now piece: Holiday is about to begin his 12th NBA season and hasn’t made it past the second round. That’s not an indictment on him (none of his teams have been favored in any postseason series between Philadelphia and New Orleans) but it’s evident that he’s a veteran like Kemba Walker at this stage of his career, ready and willing to find a contender he fits with. He’d be ready to come in and do his job at a high level, no matter if he was the first or fourth option on any given night.


Size concerns in the backcourt: While Holiday is a plus defender, pairing him in a starting backcourt with Kemba Walker would leave the Celtics looking particularly small and vulnerable against many opponents. That would challenge Brad Stevens’ versatile switching schemes and challenge Brown and Tatum to bang down low for boards even more on every single night. Holiday is a solid rebounder for his size but he’s a far cry from Gordon Hayward on that front.

Average 3-point shooter: Shooting has never been a strength for Holiday but his perimeter accuracy is trending in the wrong direction as he has increased the volume throughout his career. He hasn’t shot over 35 percent from 3-point range in any of his past five seasons when he’s attempted over four 3s per game. He would have the ability to be pickier with his shots in Boston while surrounded by better shotmakers but he isn’t a great catch-and-shoot player (36 percent from 3). Having teams dare him and Smart to beat them from 3-point range could be a winning bet for defenses some nights.

Money/contract: This is arguably the biggest hurdle for the Celtics. Holiday makes $26 million a year and Boston already has over $30 million invested in an undersized point guard in Kemba Walker. Given the big paydays coming Jaylen Brown and Jayson Tatum’s way in the upcoming years, bringing in another high priced player at a position of (arguably) strength is a questionable move. It’s possible that the Celtics might not be able to afford to keep Holiday beyond next season if he opts out in 2021 and get a hefty contract offer elsewhere. In that case, Ainge would be risking assets on a rental, something he has never been keen about doing throughout his career (see: Kawhi Leonard).


If the Celtics are willing to overlook those caveats and proceed with the win-now pursuit of Holiday, there are only two realistic paths towards a deal from a salary matching standpoint.

1. Gordon Hayward (plus a draft pick(s)) for Holiday

In all likelihood, this would be a three-team transaction since it makes little sense for the Pelicans to trade a 30-year-old on anexpiring deal for another 30-year-old on an expiring deal given the team’s trajectory. Any Hayward trade like this is only worth considering for Boston if Hayward’s camp has hinted that he wants a fresh start elsewhere and won’t be re-signing in Boston. Otherwise, Hayward and a draft pick for Holiday is largely a lateral move given their similar contract situations.

Let’s say Hayward wants out though. New Orleans will likely lock up Brandon Ingram (restricted free agent) on an extension