Once again, the Boston Celtics will soon find themselves staring at a conundrum regarding big-money players and how they will fit into their contention window.
Akin to the chaotic start to their last offseason, which saw All-Star point guard Kyrie Irving and star big man Al Horford decamp to greener pastures, the Celtics could very well see star forward Gordon Hayward walk for nothing if he chooses to opt out of the final season of his current deal.
And that’s not even the half of it.
If he does opt in, he’ll be an unrestricted free agent again in the team’s next offseason, and Boston may have to decide on ponying up on a deal that will explode their tax bill and perhaps imperil the length of their contention window, or see Hayward walk — again — for nothing.
Mike Gorman unsure if Hayward stays long-term, wants scoring in draft https://t.co/MVzY0nZXz0
— The Celtics Wire (@TheCelticsWire) October 3, 2020
But what are the issues at play?

Why are people even talking about trading Hayward?
“You mentioned their tax bill — don’t they want to lower the cost of it as part of the cap management process?” you may be asking yourself, and yes — sort of.
The Celtics want to avoid brutalizing their tax payment after Jayson Tatum’s max (or very nearly so) extension kicks in to avoid the increasing penalties of the repeater tax.
KG wants Hayward back vs Heat, but unsure of his long-term fit with Cs https://t.co/prlC4PzJYP
— The Celtics Wire (@TheCelticsWire) September 18, 2020
If they could dip out of the tax for a season altogether, that would be optimal.
But on the other hand, if they keep making deep playoff runs but fall short because ownership doesn’t spend and couldn’t even if they wanted to because of the cap situation letting Hayward walk might present, they could see a mutiny start among their key young stars.
Those who advocate trading Hayward if he opts into the final season of his current contract aren’t doing so because of what he brings (or does not) to the table as a player for the most part, but because doing so secures tradable assets for the future.
Weiss: Indy may move Oladipo, Turner; should Boston make a call? https://t.co/uGFQPgw2NQ
— The Celtics Wire (@TheCelticsWire) September 28, 2020
Proposals such as Jared Weiss’ that would see one or both of the Indiana Pacers’ Victor Oladipo and and Myles Turner returns useful players who may also be of interest to other teams even if their fit is not ideal.
Players on salaries that cannot be added above the cap unless they are developed from players or picks already under Boston’s control.
So with that in mind, let’s take a look at two general frameworks recently suggested by NBC Sports Boston’s Chris Forsberg, and a rebuttal by the Boston Globe’s Adam Himmelsbach regarding the Indiana native’s future playing for his former college coach.

Proposal No. 1: take a flier with a Motor City big man
Forsberg proposes the possibility of dealing for the Detroit Pistons’ recent All-NBA big man, who just happens to be one of the few players on max deals injured more often than Hayward. Currently rehabbing from a knee surgery, the Pistons center has two seasons remaining on his current deal.
Why would the Celtics take on a player at least as likely to be out hurt and for a season longer than Hayward at that?
WATCH: Gordon Hayward’s best plays vs. Miami in the East Finals https://t.co/UcL7vrGfvj
— The Celtics Wire (@TheCelticsWire) October 2, 2020
To state the obvious, in case he isn’t hurt.
A healthy Blake Griffin provided outstanding production for Detroit in 2018-19, and would likely see his minutes considerably reduced to accommodate floor time for starting center Daniel Theis.
Griffin would slot in well with the frontcourt-by-platoon approach given his heft and shooting provide helpful wrinkles for matchups that gave the Celtics trouble in the postseason, and can serve as the focus for another trade as an expiring deal should the first of his remaining seasons go poorly.

Proposal No. 2: Convince the Orlando Magic they need a hard reset
If there’s a team firmly planted on the dreaded treadmill of mediocrity, it’s the Orlando Magic. Could Hayward’s expiring contract be an attractive way to wrest center Nicolas Vucevic from them?
As Forsberg notes, Vucevic’s declining deal could be an ideal way to bolster Boston’s big man rotation while lessening the financial hurt of contention.
Gordon Hayward shares a photo of ‘Stache Gordon’ Jr. on Instagram https://t.co/QOq8yRToMZ
— The Celtics Wire (@TheCelticsWire) September 30, 2020
Perhaps sweetening the pot with one of Boston’s late 2020 first rounders could be enough to get the deal done; a bigger move might see other players and picks the Celtics don’t have time to wait to develop could expand the deal to blockbuster level.
Of course, such trades are a rarity in the NBA and even more so the more complex they get, which brings us to the third and most likely outcome.

Standing pat with Hayward may not be a terrible plan
If you believe the rumbles that it might be possible to convince the Butler product to return on a team-friendly deal (and hope the Horford analogue was more a product of the moment than the team) — or view the trading alternatives a bad option due to a laundry list of valid concerns — hanging on to Hayward may be the wiser option.
Gordon Hayward remains in bubble after wife Robyn gives birth to son https://t.co/hw6ZOzIN6g
— The Celtics Wire (@TheCelticsWire) September 24, 2020
He is not mercurial, and this is an organization that stood by him when he was seriously injured.
You could argue Boston had little choice after the ice-cold trade of fan favorite Isaiah Thomas, and that loyalty doesn’t pay bills as well.
All of these things are true, and even the man at the center of this conundrum may not know which of these statements are also relevant — until he does.
The Globe’s Himmelsbach is in this camp, and he’s had a longstanding relationship with the team as a beat writer, so his estimation should be taken with a grain of salt.
Appearing on a recent episode of the CLNS podcast “Celtics Beat”, Himmelsbach was skeptical that any deal for the former Bulldog was in the offing.
“He’s had some brutal luck frankly, it’s not like these injuries he’s suffering are because he’s frail or something,” Himmelsbach said, courtesy of Celtics Blog. “There aren’t a lot of Gordon Haywards out there … that’s a pretty big asset to have … the sense I’ve gotten from the organization is that they’re still big Gordon guys.”
It’s easy to forget that Stache Gordon put up close to 50/40/90 numbers last season while scoring 17.5 points, 6.7 rebounds and 4.1 assists on a team with three players averaging more than 20 points per game.
On Gordon Hayward, and making the most of things https://t.co/IGrT1ImQ0k
— The Celtics Wire (@TheCelticsWire) September 30, 2020
It shouldn’t be easy to forget he stuck around in the bubble to be there for his team despite the birth of his son (something that should never be expected of anyone, NBA player or not), or that he’s never once publicly griped about his role.
Hayward has had some terrible luck across the course of his Celtics tenure, and Himmelsbach is not wrong that none of it has been his fault, or related to who he is as a player.
In the end, it’s going to come down to the needs of the team to win another banner, but don’t expect the veteran wing to be gone simply because of popular narratives.
He’s earned more than that from Boston’s fans.