The complicated Celtics decision that could clear the Cavs’ path to contention

Jaylen Brown took a long time to consider a question about his future with the Celtics after Boston loss Game 7 of the Eastern Conference Finals to the Miami Heat on Monday.

CLEVELAND, Ohio – Jaylen Brown asked for a repeat, took a deep breath, then double-checked the question again.

“You asked what’s my thought process?” Brown said after his Celtics lost Game 7 to the Miami Heat on Monday.

Yes, ESPN’s Tim Bontemps asked how Brown felt about a potential contract extension this summer. Brown enters this offseason with one year left on his contract, and he’s eligible for a five-year, $295 million super-max extension after making second-team All-NBA this season, which makes this summer a crucial pivot point for his future with Boston.

As the NBA offseason approaches, cleveland.com will examine such questions concerning Cleveland’s main roadblocks in the Eastern Conference. The Cavs’ future depends on their rivals’ development as much as their own. And Boston’s decision on Brown is as important as any storyline in the East.

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The Celtics must decide if they deem Brown a franchise pillar. Brown must decide if he likes Boston enough to play there through the heart of his prime (an extension would keep Brown around until his age 32 season). And no matter what either party decides, the rest of the NBA – particularly aspiring contenders like the Cavs – will feel the ripple effects.

Considering the weight of Bontemps’ question, no wonder Brown needed time (24 seconds) to answer.

“I don’t really even know how to answer that question right now, to be honest,” Brown said. “My thought process is take it one day at a time, focus on getting better, focus on what the future holds, and see where we are from there, I guess. I don’t really know how to answer that.”

Boston’s decision

The Celtics can offer Brown more money this summer than any competing suitor could next. But it depends on the front office’s belief in Brown’s playmaking development and stomach for stiff luxury tax penalties.

The NBA’s governors and players’ association signed a new collective bargaining agreement in April that complicated teams’ abilities to retain multiple max-level players while adding quality talent around them. Any team that exceeds the league’s luxury tax threshold by $17.5 million or more cannot use the league’s mid-level exception, sign buyout players who made more than the mid-level on their previous contract or trade their first-round pick seven years in advance. They also can’t use cash in trades or “aggregate” contracts to match salaries in trades (example: two $10 million contracts to trade for a $20 million player). And if a team exceeds that threshold twice in five years, that same pick (seven years out) moves to the back of the first round, no matter how the team finishes during that season.

Long story shot, the Celtics will either exceed that threshold or shave key role players to get under it if they sign Brown to a super-max extension – or anything close. So Boston must be positive Brown can be part of their championship core before inking such a deal.

To that point, Brown has averaged at least 20 points on at least 48% shooting in four straight seasons. Boston has made the conference finals three times during that span and the NBA Finals once. And Brown plays good defense at the league’s most valuable position (wing).

But the Celtics’ inconsistent offense has repeatedly halted their deep playoff runs, and Brown is part of that problem. In 105 career playoff games, Brown has committed nine fewer turnovers (232) than assists. He committed eight during Monday’s loss, when Boston needed him to raise his game after Jayson Tatum turned his ankle early in the first quarter. The Celtics scored a season-low 84 points. And those datapoints will be considered during Brown’s contract negotiations.

Brown’s decision

Brown has plenty to consider beyond numbers during this negotiation. The All-Star forward prides himself as a social activist, and earlier this season he told the New York Times that he didn’t know if Boston fans supported those endeavors.

Brown said he had “run into some adversity” trying to start a business and buy a house in the city. He said that certain Celtic fans tie bad games to a player’s character. And while Brown acknowledged that not all Boston fans feel that way, “I definitely think there’s a group or an amount within the Celtic nation that is extremely toxic and does not want to see athletes use their platform, or they just want you to play basketball and entertain and go home. And that’s a problem to me.”

In a separate interview with The Ringer, Brown wondered how loyal he considered the Celtics’ front office after hearing his name in trade rumors last offseason. Boston reportedly told Brown that he and Tatum remained the team’s foundation.

Besides, he knows how the NBA does business. One week, a team loves you. The next, they’re trading you. So when The Ringer asked Brown how long he planned to play in Boston, he remained cryptic.

“I don’t know,” he said. “As long as I’m needed. It’s not up to me. We’ll see how they feel about me over time and I feel about them over time. Hopefully, whatever it is, it makes sense. But I will stay where I’m wanted. I will stay where I’m needed and treated correct.”

Have Jaylen Brown and Jayson Tatum played their final game together as Celtics?

Cavs’ perspective

The Cavs finished six games behind Boston in the East standings this season, but the gap in playoff preparedness is much wider. Brown and Tatum have played 88 playoff games together, which is 20 more games than Cleveland’s core – Donovan Mitchell, Darius Garland, Evan Mobley and Jarrett Allen – have played combined. The Cavs learned the value of playoff experience (or lack thereof) during a five-game loss to the Knicks earlier this postseason.

They also realized the challenges of playing with wings who can’t contribute on offense. Brown and Tatum might form the best wing tandem in the league. Isaac Okoro, Dean Wade and Cedi Osman rank … further down the list. You can link both teams’ postseason results to that lone factor (among others, in Cleveland’s case).

If Boston keeps Brown, the Cavs will likely encounter he and Tatum at some point during their playoff travels. They’ll need wings who can not only guard Boston’s wings but keep them honest on defense. And even then, Boston will still own the matchup.

Without Brown, that task seems less imposing, even if Tatum is a better player than any wing within Cleveland’s reach. Boston’s playoff experience, while still miles ahead of Cleveland’s, loses luster without a forward who played a key role in building it. And the Celtics’ margin for error (and injury) shrinks.

Boston has often counted on Brown to fill Tatum’s role if the ladder was hurt or slumping. But who would fill Brown’s role if Boston doesn’t re-sign him?

The Celtics’ answer to that question might sound a lot like Brown’s at the podium Monday.

Deep breath, long pause, nothing finite.

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