Should the Celtics run it back? That’s the question that has defined the offseason ever since the Celtics’ near-miss comeback in the conference finals. They couldn’t pull it off and found themselves in a peculiar middle ground between contender and pretender.
The Celtics look like a Finals-caliber team on paper and played pretty close to that standard even with two stars on their rookie contracts and a key starter looking like a shell of himself in the postseason. Still, it was apparent how short they were of their goals as the offense fell apart in the second half on a routine basis against a perfectly coached team in the Miami Heat during the conference finals. Recognizing that, it would be easy enough to hold the team together, say “we can do this with a healthy Gordon Hayward,” and carry on.
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But then The Athletic’s Shams Charania reported the New Orleans Pelicans are actively exploring a long-anticipated Jrue Holiday trade, which naturally begs the question: Should the Celtics jump in the fray?
At first glance, it makes no sense. Holiday brings the best of both worlds between Marcus Smart and Kemba Walker, though the 30-year-old could play next to both of them. But he isn’t quite the scorer Walker is nor can he defend any position and play with game-changing fire at the level of Smart. He is great in so many facets and more complete a player than either of them, but he doesn’t quite have that elite edge the two Celtics can bring to the table.
Does that matter? Would consolidating all of that talent into one player open things up for the rest of the lineup?
Before exploring that, let’s define precisely who Holiday is. The 6-foot-3, 205-pound combo guard is neck and neck with Smart for the best defensive guard in the NBA. He will turn 31 in June and is still in his prime, but he has missed more than 10 games in all but one of the past seven seasons. He hasn’t missed major time since 2015, but he is not a paragon of durability.
However, he is the gold standard of guard defense. Holiday has long been outstanding at guarding the league’s best ballhandlers, whether they be small point guards or larger wings. He reads pick-and-roll defense at an elite level and has the balance and strength to stay in the play with anyone. He’s a strong help defender, astute at sinking into the paint to disrupt the play while being able to close out to his man on the weak side without running out of the play. Much like Smart, he can handle a post-up from most power wings and even bigs.
The big difference between Holiday and Smart’s defense is the approach and energy level. Smart is a Tasmanian devil on the floor, flying around to blow up plays and try to dominate the physicality at the point of attack. Smart takes bigger gambles and is a more vocal presence, using his energy to intimidate the offense from attacking. Holiday takes a more under-the-radar approach, more disciplined in his positioning and risk-averse when it comes to fronting bigger players on post-ups or digging into the lane off his own man.
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You could argue Holiday is a little less mistake-prone than Smart, but you could make an even stronger case that Smart can stretch past his limits and make game-changing plays at a level Holiday doesn’t quite reach. But on offense, his steadiness is a stark upgrade over Smart. They fill similar roles as ball-handling guards who are decent pull-up shooters and mediocre catch-and-shoot players. They can run pick-and-roll offense, but aren’t dangerous enough scoring or distributing threats to lead a team. Put them next to some great scoring wings and they can thrive, which is exactly the situation in Boston.
This matters because the Celtics need to find a way to put their five best players on the floor at the end of games. We’ve written here plenty about how the lineup of Walker, Smart, Jaylen Brown, Jayson Tatum and Hayward could work in crunch time against most matchups, particularly because of Smart’s versatility in protecting the rim and banging with bigs. With Brown proving he can guard bigs in the postseason this year — he was tremendous against Pascal Siakam and in some scattered moments versus Bam Adebayo — and Tatum continuing to grow into a great help defender, more reps for this lineup next season could actually make that fantasy a reality. That lineup works with Smart, but it’s hard to see it happening with Holiday because of his calmer, ground-bound defensive style. The offense has inherently tremendous potential in that microball lineup, so the question is whether they can switch across the board and maintain a physical presence in the lane. That’s Smart’s edge.
That may not be the compromise, though. New Orleans is looking to move Holiday because it needs to align its star power with Brandon Ingram and Zion Williamson’s timeline. Unless the Pelicans think Romeo Langford is going to turn into the next Jerry Stackhouse, Boston doesn’t have anything to offer New Orleans that can compete with the rest of the market. So the Celtics would have to be a third-party conduit for a team looking either to pick up a ton of assets or someone like Hayward, Smart or even Walker.
Holiday’s $26.1 million salary is placed perfectly between Smart’s $13.5 million and Hayward’s $34.2 million player option to make salary matching a pain. He is actually just narrowly within the 125 percent matching range of Hayward and Walker, who is making slightly more than his teammate at $34.4 million. Pairing Smart with Langford and Vincent Poirier just gets you there, or instead deal him with a combination of Enes Kanter — if he opts into his player option as part of the deal — Semi Ojeleye (team option), Carsen Edwards or Javonte Green. So the Celtics can build a package around one of their core players that can net Holiday back.
So who are the suitors out there that may prefer one of Boston’s offerings over Holiday to facilitate a three-way swap?
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The first candidate would be the Indiana Pacers, who could be amenable to sending Myles Turner and Doug McDermott to New Orleans to bring in Hayward. The Celtics wing is an optimal fit for their new offensive direction and Indiana is home for him. Boston would likely have to send the 14th overall pick to New Orleans since Turner has become a bit overrated at this point by the public, but that gives New Orleans a J.J. Redick replacement in McDermott and a good young center on an affordable deal who can hold down the middle as Jaxson Hayes slowly develops. New Orleans had interest in Turner last year, so they seem like a solid fit. But after an underwhelming season, New Orleans may need even more draft pick compensation to make this move.
We’ve wondered how Holiday could replace Smart or even Hayward, but what about Walker? Utah could be a partner if the Celtics want to shorten their cap horizon, with the Celtics sending Walker to the Jazz and the 14th pick to New Orleans, Mike Conley and the 23rd pick moving to Utah and Holiday heading to Boston. This takes a year off Boston’s long-term commitments and reduces the tax impact with Holiday’s lower salary. There is always a chance that Holiday could opt out of his player option next season in hopes of a max deal, but that is fairly unlikely at his age. While the Pelicans don’t get a proven young player, they clear the books for the 2021 free agency bonanza and add two rookies. This makes obvious sense for Utah after Conley struggled mightily last year, bringing in a clear upgrade at a fairly low price.
Then there is Chicago. With a completely revamped front office and coaching staff, the prudent move would be to remain cap nimble and accumulate young talent as they develop their recent draft picks. But if ownership decides it’s playoff time, they could pull off a deal of Otto Porter and Coby White to New Orleans with Walker heading to Chicago and Holiday going to Boston. White had a strong enough rookie season to justify Boston holding firm on draft pick compensation, so this is a more ideal arrangement from the Celtics’ end. If New Orleans values White highly, the Pelicans have the ideal long-term point guard to fit next to their playmaking wings.
Still, it’s hard to find a deal for Boston that truly stands out as something that can give New Orleans the kind of exciting future asset it could get from other teams. Miami can offer someone like Tyler Herro, while the Warriors could send over Andrew Wiggins and the Wolves’ top-3 protected 2021 draft pick. These are the kinds of rebuild pieces that could really lift New Orleans’ trajectory to contention down the road. The Celtics are already there and they don’t need to do something drastic to bring in someone like Holiday.
(Photo: Jesse D. Garrabrant / NBAE via Getty Images)