Should the Celtics pursue a James Harden trade?

Danny Ainge has a track record of swinging for the fences as a general manager when the opportunity presents itself. He did it first back in 2007 with Kevin Garnett and Ray Allen, bringing Boston a championship and the potential for more titles had it not been for injuries. His next big swing fell short in 2017 with Kyrie Irving, as he bet big on a wildcard All-Star that ultimately burned some of the C’s recent upside after walking away with no compensation following an underwhelming two seasons.

Now there is a potential new option on the table as free agency approaches in the NBA this week: James Harden. The perennial MVP candidate turned down an extension with Houston that would have paid him over $50 million per year, according to ESPN. After Russell Westbrook asked out last week, Harden is next in line, pushing for his way out the door to start fresh with a contender. Shams Charania has reported that Brooklyn and Philadelphia are Harden’s top two desired destinations and that the Rockets are prepared to keep him for at least the season (he has three years left on his deal). While there’s plenty more to say about Harden’s request and the motivation behind it, for now we’ll focus on how this affects Boston. Will the Celtics make a run at him? And if not, how might Harden’s future affect Danny Ainge’s plans for the Celtics for next season and beyond? Let’s try to make sense of the particulars of a complex situation.

What’s Harden’s contract situation?

The 6-foot-5 guard has three years remaining on his contract entering the 2020-21 season. He will be the fifth-highest paid player in the NBA next season with a salary of $40.8 million. He is set to make $43 million in 2021-22 and the final year of his deal ($46 million) is a player option. Trading for Harden now guarantees a team two years of the 31-year-old in the tail end of his prime.

What would the Celtics have to give up for him?

Jayson Tatum would be off the table for the Celtics in negotiations here, but anyone else would be fair game. A starting offer for Houston would have to trend towards the younger side of things, so we begin with Boston’s next best trade assets in Jaylen Brown and Marcus Smart. Brown has All-Star potential and is under team control for four years at a below-market rate, making him the centerpiece of any deal. From there, Smart adds another starter-level player in his prime that has two years remaining on his below-market deal. Smart could serve as a trade chip for Houston in another deal or a core piece of their next chapter. A lot of people will suggest Kemba Walker or Gordon Hayward in place of those guys for the salary matching, but the Rockets aren't going to want to bring back 30-year-olds on big deals when they are trading away Harden.

Together, Smart and Brown would create the baseline of an offer from a salary matching standpoint as they combine to make $36 million together — which is enough money to salary match Harden’s hefty deal. From there, it would come down to draft picks and young players. The Celtics have three first-round picks for 2020 to offer as well as all of their own future first-round picks. Those future picks would not have much value (since they would be coming from an expected contender) but the multiple choices this year give Houston the possibility of getting the best of both worlds in the forms of young talent (Brown, Smart) and future prospects. The Celtics also have a long list of 23 and under bench players (Robert Williams, Romeo Langford, Grant Williams) that could serve as sweeteners to a potential package, especially if the deal were to expand to include other Rocket veterans.

Could the Celtics outbid other suitors if they wanted to?

The answer depends on how much the Rockets' front office likes Jaylen Brown compared to other top young prospects around the league, so let's take a look at a few different spots.

Brooklyn: There’s little doubt that the Celtics (and about 20 other teams around the league) could top an offer from Harden’s preferred destination of Brooklyn. There is an intriguing young piece there on a good value deal in Caris LeVert, but their other top movable talent is on expiring deals (Spencer Dinwiddie, Jarrett Allen) and all of their future draft capital that could be offered won’t be any good if Harden forms a superteam with Kyrie Irving and Kevin Durant. The Nets can offer up to four future first round picks through 2027 along with pick swaps, but that’s likely far from the best deal Houston could find.

Philadelphia: The next obvious suitor here is the Sixers with former Rockets GM Daryl Morey at the helm. Ben Simmons would be the obvious piece to dangle here for Houston, since his value trumps Jaylen Brown’s and he’s still under team control for the next four seasons as well, making him an attractive centerpiece to a deal. The Sixers don’t have a second strong player like Smart to add to the deal with good team control, but their draft capital is roughly on par with Boston for the next decade with no extra first-round picks.

Around the rest of the league, it’s hard to find teams that could compete with what the Celtics and Sixers could put on the table. Would Denver trade an emerging All-Star in Jamal Murray for a couple of years of Harden? Would the Heat trade a host of their young talent and future draft picks (Tyler Herro, Duncan Robinson, Kendrick Nunn) to try to pair Harden with Jimmy Butler? It’s hard to see that offer being enough for Houston without Bam Adebayo getting involved and that’s probably a bridge too far for Pat Riley, especially since the Heat will have the cap room to just sign a star outright next offseason in free agency.

The Lakers and Clippers don’t have enough to get him without moving one of their stars (not happening). The Thunder have all the draft picks in the world but are rebuilding. There’s no deal for the Jazz without Donovan Mitchell involved and that’s not happening since it's hard to envision Harden sticking around long-term in Utah. The Mavericks already have a ball-dominant guard in Luka Doncic and don’t have enough player assets left on the roster to get heavy consideration without using him. Every other team in the league isn’t close enough to contending to risk bringing in a disgruntled Harden or simply don’t have the assets to pull it off (Bucks, Raptors).

That leaves the Celtics, Sixers and Nuggets as the potential suitors here with Brooklyn strictly getting pushed from the Harden camp.

Should and will the Celtics take a run at him?

It would be foolish for Boston not to inquire about one of the best players in the league. Harden has led the NBA in scoring for three consecutive years now and has made the All-Star game for eight straight years while performing as one of the most durable players in the NBA. He has not missed more than 10 games in a season before and has been the architect of one of the best offenses in the league since 2012.

Harden can posture all he wants about going to Brooklyn, but with two years left on his contract, he isn’t exactly in a great position to force the Rockets’ hand to a preferred destination. When the Celtics acquired Irving two years ago, Boston wasn’t on his original list of preferred destinations out of the shoot. However, the Celtics had the best offer and had a contending setup that was agreeable, so a deal ultimately got done between the East rivals.

On the heels of seeing another top rival in Milwaukee land a potential trade target in Jrue Holiday on Monday night, the sense of urgency for the Celtics should be on the rise in an already imposing Eastern Conference. Chasing Harden would be a similar move in many ways to Irving (two years remaining on deal, coming to Boston not first choice) but he’s also a far better player than Irving. A core of Kemba Walker, James Harden and Jayson Tatum would probably be a lock for a top-3 NBA offense for the next few years, which should be enough to cover up the warts in a subpar defensive backcourt. Ainge would have to fortify a roster of defensive role players and shooters around this group to maximize them, but that’s a top three that could go against anybody in the league (assuming Walker is healthy).

On the flip side, the situation with Irving will have to give the Celtics a bit of a pause. Brown and Smart are beloved by Celtics ownership and the front office, so moving on from both with numerous other assets would be tough ask for some in the organization. There are also plenty of questions to ask about the Harden/Tatum pairing. Would Tatum be okay with being the second banana? Are they an ideal fit together? Bringing in Harden improves the team’s contending chances in the interim, but what happens if things go sour? Harden could still walk away for nothing in two years and there would be nothing left to build around Tatum, risking his long-term future in Boston as well.

Unlike other teams this offseason, the Celtics probably feel like they don’t necessarily need to do anything big to the roster. Sticking with Brown and Smart is a safe choice for the long-term trajectory of the franchise and one that will guarantee a potentially longer window of contention. Will that core be good enough to ever get out of the East though with the way other contenders are stacking the deck? A lot of that depends on the future of Gordon Hayward and health of Kemba Walker, but putting the Celtics fourth in the East power rankings right now isn’t a reach. Internal improvement and top-tier drafting will be Boston’s only path to success if they stand pat with this core.

Ultimately, Harden may be the last big prize on the trade market this offseason and it will certainly be the most expensive one. Does Ainge risk watching Harden form a superteam with a divisional rival in Philly or Brooklyn? Or does he pool his assets together for one big swing to raise the Celtics’ ceiling immediately? The window for Boston’s best trade offer to Houston will be gone by Wednesday night, as the team’s three first-round picks will need to be used in some form, so timing matters here.

Ainge should be ready to take a swing, but based on how the Irving situation unfolded, the Celtics will likely proceed cautiously with any offer to bring in a guy who has his eyes set elsewhere for the long-term.