Giannis Antetokounmpo

As the Milwaukee Bucks continue to try to convince Giannis Antetokounmpo to re-sign, their addition of Jrue Holiday may have been a good way to entice the reigning two-time NBA MVP. 

On the most recent episode of the Brian Windhorst & The Hoop Collective podcast (h/t HoopsHype.com), ESPN's Malika Andrews reported "people close to Giannis (said) that that was a good signal that they were able to get a guy like that who is a little bit better shooter than Eric Bledsoe."

Antetokounmpo is eligible to sign a supermax contract with the Bucks until Dec. 21. An extension would be worth $228 million over five years. 

Windhorst reported Monday that the feeling from the Bucks front office is they have "gone from cautiously optimistic to cautiously confident in recent weeks" that they will be able to keep their franchise player. 

Milwaukee officially acquired Holiday from the New Orleans Pelicans on Tuesday as part of a four-team deal that included the Denver Nuggets and Oklahoma City Thunder. The Bucks sent Bledsoe, two first-round draft picks and the rights for two pick swaps to New Orleans. 

Milwaukee dealt George Hill to the Thunder, while the Bucks' draft rights to R.J. Hampton went to the Nuggets. 

Holiday is regarded as one of the NBA's best two-way guards. The 30-year-old has averaged at least 19 points and six assists per game in each of the past three seasons. 

Antetokounmpo is entering the final year of his contract with Milwaukee. The Greek Freak has led the franchise to the NBA's best regular-season record in each of the past two seasons, but it has been eliminated in the Eastern Conference Finals and Semifinals, respectively. 

The Los Angeles Lakers' offseason is likely just about wrapped up. In are Montrezl Harrell, Marc Gasol, Dennis Schroder and Wesley Matthews. Gone are Rajon Rondo, Avery Bradley, Dwight Howard and JaVale McGee. 

And returning are Kentavious Caldwell-Pope, Markieff Morris and...Anthony Davis?

While everyone is rightfully assuming that Davis will sign a lucrative extension with the Lakers this offseason, he hasn't done so to this point. But there could be a very interesting reason for that, as Brian Windhorst noted on ESPN Radio on Monday (h/t RealGM):

"I think there are two star players waiting to sign to see what Giannis Antetokounmpo does. That's Anthony Davis. He's coming back to the Lakers, but he may change the alteration of his contract, the way it's structured, to give the Lakers a window, if not for Giannis but for somebody in a one-plus-one. Because that's what LeBron James is now on."

The other star player he mentioned was Bam Adebayo, who has since signed a five-year max extension that could be worth up to $195 million.

OK, let's unpack this. 

If Antetokounmpo doesn't sign an extension by Dec. 21 with the Milwaukee Bucks, he'll be a free agent after the 2020-21 season. James, as Windhorst noted, is under contract this season for $39.2 million and has a $41 million player option for the 2021-22 campaign. Davis could choose to go that route as well, leaving himself with maximum flexibility heading into what could be a wild 2021 summer. 

Remember, it isn't just the Greek Freak who could head toward free agency. Kawhi Leonard, Paul George, Chris Paul, Blake Griffin and Jrue Holiday also have player options for the 2021-22 season. Players such as Rudy Gobert, Mike Conley, Andre Drummond, Victor Oladipo, DeMar DeRozan and LaMarcus Aldridge will be straight up free agents. 

We could see another seismic shift of talent around the league, much as we did before last season. The ability to hit free agency yet again next summer would offer Davis and James the ability to opt out of their deals to help the Lakers bring another star aboard before re-signing with the team. 

It's fair to question if the Greek Freak would be the right fit with James and Davis, but both players opting out at the same time would give them a ton of leverage when it comes to building a roster around them. James signed similarly short deals with the Cavaliers in his second stint with the team, ostensibly to ensure the Cavs were consistently motivated to surround him with talent. 

If Antetokounmpo doesn't sign his extension, next summer could be wild. New super teams could form. It's easy to see why Davis might want to have flexibility to meet a potentially changing NBA landscape. 

We've perhaps already seen an example of Davis' input factoring into the team's roster-building this year in the retaining of Morris, per Brad Turner of the Los Angeles Times:

"I think the market was getting really, really dry for (Morris) and some players, so in this case Markieff knew the best place for him was with the Lakers, but how about this? There is a guy named Anthony Davis who wanted him back. He wanted him back because he's tough, because he plays defense, he rebounds, he can shoot the three, open up the court and again he's a versatile player. One thing the Lakers really loved having and have had success with is players who can play offense and play defense, and don't mind being a good teammate and in the locker room."

Morris played well last season, averaging 5.9 points and 3.0 rebounds per game in the postseason, primarily coming off the bench, while shooting 42.0 percent from three. He was the ideal role player for the Lakers, and his return appears to be at least somewhat a reminder of the pull Davis has with the Lakers. 

Keep that pull in mind if Davis indeed signs a two-year extension this offseason with a player option in the second season. 

For months, Thanasis Antetokounmpo, Giannis Antetokounmpo's brother and a Milwaukee Bucks guard, stayed in regular contact with Bogdan Bogdanovic. They spoke numerous times over the phone, sources said, with Thanasis hoping to eventually court the guard's services this offseason. During a few calls, Giannis communicated his desire in teaming with Bogdanovic.  

Aside from the obvious spacing Bogdanovic's shooting would provide Milwaukee's offense, Giannis admired his fellow European's toughness and swagger, sources said. He viewed Bogdanovic as someone you could go to war with in the postseason.  

Antetokounmpo grew increasingly focused on teaming with Bogdanovic. The Sacramento guard quickly presented Milwaukee's greatest option as the Bucks dealt with a hamstrung cap sheet and limited trade assets.  

When word arrived last week of the Bucks' Monday night coup—agreeing in principle to acquire both Jrue Holiday and Bogdanovic in the waning hours of the league's renewed transaction window—there was an overwhelming sense around the organization, and people with knowledge of Antetokounmpo's thinking, that he would accept the Bucks' supermax extension offer—the ultimate objective of the franchise's 2020 offseason. 

A week later, Bogdanovic plays for the Atlanta Hawks, not the Bucks. And there has since been a categorical step back in the Bucks' confidence in getting a long-term commitment from their superstar, even if Antetokounmpo ultimately accepts the franchise's offer of a five-year, $228 million supermax extension. 

There has long been optimism Giannis Antetokounmpo will re-sign with the only franchise he's ever known. Any figure around the Bucks, or who has spent time around Antetokounmpo, has always spoken of the superstar's unwavering loyalty. This is a person who once refused to attend the NBA draft unless his brother could come along with him. By all accounts, he enjoys the decibel levels of Milwaukee's market. He does not yearn for the lights of New York or Los Angeles.  

It's also said that Antetokounmpo values being not just the face but the bedrock of the franchise. That is not to characterize him as brimming with ego, rather pride in carrying himself like an organizational pillar. He relishes the responsibility of leading Milwaukee to a championship, like the stars he grew up watching before a wave of player empowerment swept the league. 

And while he may indeed commit to the Bucks before his Dec. 21 deadline, at this juncture, no news is not good news for Milwaukee. At the moment, Antetokounmpo remains in Greece, where he's been training ahead of the regular season. 

Antetokounmpo was pulling levers to help the Bucks help themselves. He had listed several wing players he hoped the Bucks could land in order to fortify his surrounding cast for a better effort at the 2021 championship. Wizards All-Star Bradley Beal was never a realistic option. Pacers All-Star Victor Oladipo was discussed in numerous trade scenarios, sources said, but Indiana ultimately declined Milwaukee's advances. At one point, that included a discussion of Donte DiVincenzo, George Hill and the No. 24 pick in the 2020 draft. 

After agreeing to the parameters of a deal for All-Star point guard Jrue Holiday, the Bucks made a series of free-agency signings to replenish Anteotkounmpo's supporting cast. Milwaukee added a premier backup point guard in D.J. Augustin, a dangerous shooter in Bryn Forbes and a defensive specialist in swingman Torrey Craig. Bobby Portis will also join the Bucks on a one-year deal. 

The sum of these additions simply doesn't equal the impact landing Bogdanovic would have made for Milwaukee, both in terms of adding firepower to the Bucks offense and earned goodwill from Antetokounmpo. 

Sacramento had every reason to engage Milwaukee in trade discussions. Bogdanovic was set to hit restricted free agency this season, and by all accounts, the 28-year-old was searching for an optimum payday the Kings were not entirely prepared to match. The Bucks, sources said, were hoping to agree to a framework of a sign-and-trade that could effectively take Bogdanovic off the market right when free agency was set to open Friday. 

Early conversations centered on sending Eric Bledsoe and the No. 24 pick to Sacramento, sources said. But the Kings insisted on guard DiVincenzo being included in any deal, just as the Pacers did in the talks regarding Oladipo, according to sources. 

Any deal that brought Bledsoe—and the three years, roughly $54.4 million remaining on his contract—back to Sacramento would have cleared the necessary room under the $139 million apron for the Bucks to offer a competitive salary to Bogdanovic. Sacramento brass had known from conversations with Bogdanovic's representatives that the guard was seeking an average annual salary around $18 million. 

Yet all the while, Milwaukee remained in aggressive pursuit of Holiday. And by all accounts, New Orleans management successfully engineered a bidding war for Holiday's services. The Boston Celtics offered Gordon Hayward plus their three first-round picks in last week's draft, it is said. Atlanta is known to have discussed the No. 6 pick, Dewayne Dedmon and sharpshooting youngster Kevin Huerter. Denver and Dallas were also rumored as significant suitors. 

The clock was ticking. Only 48 hours remained before the draft. And despite Bledsoe's salary number being an apparent necessity to match Bogdanovic's preferred number in free agency, Milwaukee moved forward with its Holiday acquisition. 

Bledsoe was also always a centerpiece in any trade for Holiday, one source said. 

Milwaukee went forward in swapping Bledsoe, Hill and three first-round picks, plus two pick swaps, for Holiday. And with limited remaining draft capital to play with, the Bucks returned to talks with Sacramento by reluctantly bringing DiVincenzo onto the table. Milwaukee officials remain bullish on the Villanova product, sources said, but they viewed Bogdanovic as a necessary target in line with Antetokounmpo's wishes. 

Adding Holiday was an obvious upgrade, but Bogdanovic was communicated as Antetokoumpo's preferred addition all offseason. The Antetokounmpo brothers had tried to lure him with the promise of forming a Big Three with Giannis and Khris Middleton. Holiday was an added bonus. 

So with DiVincenzo made available, sources said, the Bucks and Kings agreed in principle early last week. Along with DiVincenzo, Milwaukee would send Ersan Ilyasova and D.J. Wilson to Sacramento in exchange for Bogdanovic and Justin James. Come that Friday, the Bucks would have been able to negotiate contract terms with Bogdanovic's representatives once the free-agent market opened at 6 p.m. ET.  

All players included within the trade framework were notified, sources said. Over the next two days, one Bucks player and his girlfriend were already searching for new homes in Northern California. A real-estate agent even visited one of the properties and sent pictures of the interior. 

Late that Monday evening, just minutes after the agreement was struck, word reached the news media of Milwaukee and Sacramento's intended sign-and-trade. And during the board of governors' call on Tuesday, several league sources indicated that Bucks governor Marc Lasry stopped just short of bragging about Milwaukee's impressive Monday evening of transactions. However, multiple league personnel participating on the call said they did not remember any Bucks official gloating or any noted behavior or conversation out of the ordinary. 

Either way, at least one rival team filed a formal complaint to the league office Wednesday, sources said. And by that afternoon, the league informed both Milwaukee and Sacramento that it would open an investigation into an alleged sign-and-trade already being agreed to four days before free agency had begun. The league also sent a memo to all 30 teams that afternoon reminding franchises of the NBA's anti-tampering policies, encouraging teams not to "jump the gun" in contacting players under contract with other teams and warning punishments of up to $10 million and draft-pick forfeiture.  

At that juncture, it became clear Milwaukee was no longer a possible landing spot for Bogdanovic. He could have engaged with Bucks leadership Friday, but moving forward with Milwaukee instantly became untenable for the 28-year-old. It would be far too precarious to move forward with the Bucks at the risk of the NBA ultimately determining foul play and blocking the transaction.  

Bogdanovic's camp insisted they never discussed the particulars of an agreement with Bucks officials and that they were only made aware of the negotiations. Bogdanovic even phoned the Antetokounmpos and reiterated he had never agreed to any contract with Milwaukee. 

No matter the intent, no matter the news of Milwaukee and Sacramento's agreement, all indications are the league office would have investigated such a transaction. Commissioner Adam Silver has been as stringent on eliminating evidenced tampering as Giannis has been in wanting Milwaukee to improve its roster.  

And all indications suggest the scale is still tipping in the Bucks' favor. Yet the collapse of this Bogdanovic sign-and-trade leaves the door far too open for a possible Antetokounmpo departure than Bucks officials would like. 

The Miami Heat reportedly plan to pursue Milwaukee Bucks forward Giannis Antetokounmpo if the two-time NBA MVP enters free agency next summer, but All-Star center Bam Adebayo's five-year max extension would force the Heat to be more creative in reaching that goal due to salary-cap concerns.

However, Anthony Chiang and Barry Jackson of the Miami Herald reported Tuesday that the Heat may have earned themselves some goodwill with the two-time MVP: 

"A source who knows Antetokounmpo well said he would be more impressed by the Heat giving Adebayo the extension now than asking Adebayo to wait a year for the purpose of making it easier for the Heat to acquire Antetokounmpo. Adebayo and Antekounmpo are friends and share the same agent, Alex Saratsis."

The Heat are rumored to be going "all in" on signing Antetokounmpo in the summer of 2021, per Shams Charania of Stadium and The Athletic. 

Chiang and Jackson also said Antetokounmpo remains "the Heat’s primary target in 2021 free agency."

As the Miami Herald duo noted, Antetokounmpo has until a Dec. 21 deadline to sign a supermax extension with the Bucks. If he does not do that, then he will enter free agency next summer.

Chaing and Jackson explained how the Adebayo extension complicates that pursuit:

"Adebayo’s cap hit for 2021-22 would be $15.3 million if Miami waited until next offseason to give him a new contract. His 2021-22 cap hit is expected to be at least $28.1 million with his max extension.

"That difference of about $13 million is huge, because it makes it realistically impossible for Miami to sign Antetokounmpo—or another free agent such as Victor Oladipo—using cap space."

Therefore, a sign-and-trade would be the likely path to go for Miami.

On Adebayo's end, he told Ira Winderman of the South Florida Sun-Sentinel that he is currently unaware of Antetokounmpo's future intentions at the moment.

The 2020-21 NBA season is scheduled to begin Dec. 22.

Anthony Davis has yet to sign a new contract with the Los Angeles Lakers, and his final decision may hinge on whether Giannis Antetokounmpo takes a supermax deal with the Milwaukee Bucks.

ESPN's Brian Windhorst reported Monday on Keyshawn, JWill & Zubin that Davis could be waiting on the two-time reigning MVP so that he could structure his deal to open a window for the Lakers.

"I think there are two star players waiting to sign to see what Giannis does," Windhorst said (via RealGM). "That's Anthony Davis. He's coming back to the Lakers, but he may change the alteration of his contract, the way it's structured, to give the Lakers a window, if not for Giannis but for somebody in a one-plus-one. Because that's what LeBron is now on.

"And Bam Adebayo. If Bam Adebayo signs a max contract, the Heat will not have the room. But if he waits a year, then they will."

Teams are already planning for what could be a free-agent bonanza in 2021. In addition to Antetokounmpo and Adebayo, Paul George, Kawhi Leonard, LeBron James, Rudy Gobert, Chris Paul, Blake Griffin, Jrue Holiday and Victor Oladipo are eligible to hit the market.

General managers are doing what they can to keep their 2021-22 salary-cap commitments as flexible as possible.

Goran Dragic, Andre Iguodala and Meyers Leonard all have team options for the Miami Heat in 2021. According to Sportsnet's Michael Grange, the second year of Fred VanVleet's four-year, $85 million contract declines by 8 percent from his starting salary of $21.3 million, thus giving the Toronto Raptors a little wiggle room. The Lakers have five players signed to deals beyond 2020-21.

Even if the team has the cap space to do so, signing Antetokounmpo might be tough for Los Angeles.

Kevin Durant's time with the Golden State Warriors showed how joining what's already a championship-winning squad may not be all that fulfilling. Antetokounmpo could be wary of making a similar jump to the Lakers or whoever is coming off a title run in the 2021 Finals.

But even if they don't land Giannis, the sheer volume of talent that figures to be available gives the Lakers plenty of incentive to allow themselves the opportunity to pair another star alongside Davis and James.

The Milwaukee Bucks have reportedly gone from being "cautiously optimistic to cautiously confident" that superstar Giannis Antetokounmpo will sign a five-year, $228 million supermax contract extension this offseason, according to ESPN's Brian Windhorst.

Per that report:

"The moves they've made telegraph their confidence. They didn't trade three first-round picks and two pick swaps for Jrue Holiday without insight. There's no question Milwaukee felt the need to make roster upgrades, especially in the backcourt, after last season's playoff disappointment. That is part of a case being made to the reigning two-time MVP. But the Bucks were also acting with confidence that they weren't mortgaging a future without Antetokounmpo. They hope."

But Windhorst added that there are "teams clearly hedging that Antetokounmpo will not extend his deal before the Dec. 21 deadline," including the Miami Heat, Dallas Mavericks, Toronto Raptors and New York Knicks, which all conserved 2021 cap space. 

Those teams aren't alone. Windhorst reported that "for more than a year, teams have been building dossiers, from the role of the closest people in his life—his longtime girlfriend and his brothers—to his admiration for international players who have come over to become successful like him. That and other intel has been collected to use if an opportunity arises."

It's no surprise. The 25-year-old Antetokounmpo is a two-time defending MVP and one of the truly signature talents in the game, combining unique size, athleticism, scoring at the basket and playmaking. While that hasn't translated into a championship—or even a trip to the NBA Finals yet—it could be argued Milwaukee's postseason failures have had more to do with the team's supporting cast than its best players. 

Hence the team's huge overpay for Holiday. The Bucks should be better with a starting five of Antetokounmpo, Holiday, Khris Middleton, Brook Lopez and D.J. Augustin than they were a year ago.   

Will that roster be good enough to convince Antetokounmpo to bypass free agency to sign the supermax?

He would be giving up leverage for money if he signed the extension. Milwaukee can offer him $83 million more in an extension than he can get as a free agent, per Windhorst, but Antetokounmpo's ability to potentially sign elsewhere—or sign shorter deals with the Bucks—offers him the ability to keep the pressure on Milwaukee's front office to consistently build a winner around him. 

If Antetokounmpo is happy with Milwaukee's offseason, perhaps holding onto that leverage loses its relevance. We'll have a better idea by Dec. 21.