Tamika Tremaglio, the executive director of the N.B.A. players’ union, organized a friendly social gathering ahead of this season between union officials and N.B.A. league executives: party games, cocktails and even a five-on-five basketball game. They would spend much of the next few months negotiating against each other for the next collective bargaining agreement, and Tremaglio first wanted them to have a little fun together.
Tremaglio and N.B.A. Commissioner Adam Silver competed against each other in an egg toss.
“For our benefit,” she said, “Adam and I, we didn’t have to play basketball.”
The tenor of the relationship between the league and its players’ union seems a far cry from the contentious moments that have dotted their history: the players’ very first attempts to unionize in the 1950s; tense years in the 1990s; and antagonistic battle in 2011 that led to the league’s most recent lockout.
Recently, the N.B.A.’s labor landscape has been peaceful, but the strength of that collegiality is being tested by pressure points during a negotiation that has addressed issues like the age limit for players entering the league, a possible in-season tournament and the league’s luxury tax system.
One of those pressure points might come this week as the deadline for either side to opt out of the current agreement looms on Friday. Silver said on Wednesday afternoon that he can foresee a deal being reached by Friday, but the league would likely opt out if not. That would make the current collective bargaining agreement expire on June 30 instead of after the 2023-24 season and add urgency to the negotiations for a new agreement. Tremaglio said in a statement that the union does not plan to opt out.
“If we don’t have a deal and the league decides to opt out, it will be disappointing considering all the work both sides have put into the negotiations, and the fair nature of our requests,” Tremaglio said.
Whatever happens will be set against the backdrop of an era in which N.B.A. players and team owners have largely cooperated, making their dynamic look far different from the labor fights that have played out recently across numerous industries in the United States.
People on both sides refer to the relationship between players and team owners as a partnership, and they often develop friendships with each other. During this period, star players have immense power over their careers on and off the court, and the league has benefited from lucrative media rights deals.
“It’s not like you can draw a line and say previously it was bad and now it’s good or anything else,” said Jeffrey Kessler, the principal outside counsel for the union, who has been working with the union since 1978. “It just varies over time, shaped by a lot of different forces, shaped by the economics at the time, shaped by the personalities at the time, shaped by the experience. They go through different cycles.”
Finances, as they often do with collective bargaining in any industry, have shaped the tenor of the relationship for decades. In 1954, when N.B.A. players first tried to organize, back pay for a group of players was among their top issues. The league recognized the union three years later.
Over the next several decades, issues like pensions, free agency and players’ share of league profits became sticking points.
“We were the first ones to establish a percentage of the growth revenue going to the players,” Junior Bridgeman, a former player, said, referring to the 1983 C.B.A., two years before he began his tenure as president of the players’ union as the league’s popularity was growing because of Magic Johnson, Larry Bird and Michael Jordan. “No one thought at the time that the numbers would get to where they are today and it would be as meaningful as it is today.”
Today, Bridgeman is a business magnate who built a fortune in the food and beverage industry, but when he first attended bargaining sessions, he considered it an unofficial curriculum for a master’s in business administration. He saw what mattered to the team owners and how they communicated.
“Most of the meetings ended up being contentious to some extent,” Bridgeman said. He added: “We went to one meeting that lasted all of seven minutes. We got up and walked out. It was the art of negotiation in real life.”
In 1995, the league locked out the players for the first time. Union leadership and the league’s representatives had agreed to a deal, but players were unhappy with basic terms and the way the negotiation was conducted. A group of high-profile players filed an antitrust lawsuit and moved to decertify the union.
They reached an agreement before the season began, but the deal had an opt-out clause that eventually led to the longest lockout in league history, nearly canceling the 1998-99 season. The sides reached an agreement in January 1999.
Silver has worked for the N.B.A. since 1992, spending much of his early years in N.B.A. Entertainment. He became the league’s deputy commissioner, serving under David Stern, in 2006, the year an age limit of 19 went into effect for the draft.
The league’s next work stoppage came in 2011. Stern appointed Silver as the league’s lead negotiator for those talks. Silver chuckled at the title.
“When David Stern is in the room, he’s the lead negotiator,” Silver said in a phone interview Monday.
Stern, who died in 2020, was indeed still the face of those negotiations. His biting wit and tough demeanor led to memorable moments. Billy Hunter, then the union’s executive director, once said he thought the league’s claim that it was losing $400 million a year was “baloney.” Stern, whose family owned a deli, quipped in response: “I grew up at Stern’s delicatessen. He has his meat wrong.”
As a player, Michael Jordan had been heavily involved in union battles. His name was on the antitrust lawsuit Kessler filed on the players’ behalf in 1995.
In 2010, he became the majority owner of the Charlotte Bobcats, now the Hornets, and took an active role in labor negotiations later that decade. He is now the chairman of the labor relations committee.
“The expectation maybe from some people on my side that when Michael was at the table, everything would be hunky-dory,” Silver said. “‘Oh, Michael Jordan is saying it. Therefore that must be a fair position.’”
Players, he said, didn’t agree. Silver recalls the star guard Chris Paul, who was the president of the union from 2013-21, telling him: “No question I admire and trust Michael Jordan, but we’re now, in essence, adversaries in this process.”
Silver believes the relationship between players and the league is more trusting now than in previous bargaining cycles, in part because the league is more open about its finances.
“It doesn’t necessarily mean that it makes it easier to get a deal done,” Silver said. “But we’re now able to jump over what used to be months of back and forth over what the so-called truth was regarding the league’s financials.”
Paul, who was drafted in 2005, said he has seen players become more interested and involved in understanding the business of the league now than earlier in his career. Silver has made a point to build personal capital with players. He also fostered a close relationship with Michele Roberts, Tremaglio’s predecessor, who held the post from July 2014 to January 2022. Roberts declined to be interviewed for this story to avoid the appearance she was trying to influence negotiations from retirement.
“That’s one of his strengths,” Jerry Colangelo, who was an executive for the Bulls in the 1960s before leaving to work for and later own the Phoenix Suns, said of Silver. “He’s a communicator, a terrific communicator. David was a little bit more arm’s length.” He added: “Both are really good negotiators. Both really could be very tough when they need to be tough. But on a personal basis, Adam is more available.”
Both Silver and Paul said that doesn’t mean negotiations are easier.
“They always get contentious,” Paul said.
Where that productive relationship helps is in times of unexpected upheaval, like when the coronavirus pandemic hit and caused the league to shut down operations in 2020.
“The shutting down of the business, playing in a bubble in Orlando, all those things were far outside the scope of our agreement,” Silver said. He added: “The trust enabled us to sit down with the leadership at the union and with the leaders — and with the players’ executive committee — and we worked through some really difficult issues.”
Their shared stakes also helped them navigate the work stoppage that occurred in the bubble when players, led by the Milwaukee Bucks, decided not to play after a white police officer in Kenosha, Wis., shot a Black man named Jacob Blake. Before games resumed, players met with team owners over videoconferencing and asked them to commit to support social justice concerns.
During the pandemic stoppage, Silver said he and other key league executives began having daily calls with Paul, guard Kyle Lowry and center Dwight Powell, who were part of the league’s competition committee. They checked in on how players were feeling about issues like returning to play, their own safety and the racial justice movements that were sweeping the country.
When CJ McCollum replaced Paul as president of the union in August 2021, he was added to those calls. Silver said the calls are no longer daily, but still happen regularly.
“We talk about everything,” McCollum, a Pelicans guard, said of his relationship with Silver. “The state of the game, where the game is at, ways to improve.”
This season they discussed topics like an uptick in travel calls and changes to foul calls. When the W.N.B.A. star Brittney Griner was imprisoned in Russia, McCollum said they sometimes discussed what they could do to help the efforts to free her.
Tremaglio, the N.B.P.A.’s executive director, said the party last fall helped her bolster her relationships with league executives, too.
“We are in business together, right? We have a partnership,” Tremaglio said. “For me, I tend to do business with people that I like and know something about.” She added: “I thought it was really critical before we go into negotiations that we had a chance to really get to know one another.”
There were some new faces in the union and new faces in the league office, and most of their interactions during the past several months had been held remotely.
“I share her view,” Silver said. “I thought it was a great idea.”
He added: “When you negotiate with a players’ association, or frankly any collectively bargained relationship, you get a deal done and then the next day you’re dealing with those exact same people and you’re living under that deal.”
Tremaglio said the union won the games, though league sources dispute that contention. The stakes were lower that day, but their competitive natures persisted.