NBA free agency 2023: Day 1 winners and losers, starring Fred VanVleet and Bruce Brown

Folks, your winners and losers from the first night of 2023 NBA free agency ...

WINNERS

Houston Rockets

The Rockets' plan to pursue Fred VanVleet, Brook Lopez and Dillon Brooks was widely known in league circles well before free agency opened, and Houston landed the first of them on Friday night, guaranteeing VanVleet his maximum of $130 million over the next three seasons. Even if the Rockets fail in their attempts to spend the entirety of their $66 million in cap space on the opening night of free agency, they succeeded.

VanVleet was the only recent All-Star to change teams on Friday. The 29-year-old brings table-setting (19.3 points per game on 40% 3-point shooting and a 3-to-1 assist-to-turnover ratio over the past four seasons), championship experience and the grit it requires to make more than $200 million in salary as an undrafted player to a young Rockets team that has not won more than 22 games in any of the past three seasons.

There is little doubt that recent top-three picks Jalen Green and Jabari Smith Jr., who were playing with 22-year-old shoot-first wing-turned-point guard Kevin Porter Jr. this past season, will benefit from VanVleet shepherding the offense. VanVleet can also mentor promising rookie point guard prospect Amen Thompson and play alongside him. VanVleet won a title with the Toronto Raptors as Kyle Lowry's backcourt partner.

VanVleet will be an extension of new Rockets head coach Ime Udoka's hardline approach that demands toughness on defense and intelligence on offense. Brooks and Lopez could also balance those scales on a Houston team that needed direction. The Rockets have chosen a path, and VanVleet is the first step on it.

Rich Paul, Klutch Sports CEO

The list of Paul's clients who agreed to deals on the opening night of free agency: Jerami Grant ($160 million), VanVleet ($128.5 million), Draymond Green ($100 million), Trey Lyles ($16 million), Troy Brown Jr. ($8 million) and Cam Reddish ($4.6 million). Klutch Sports is also reportedly negotiating an extension for Gary Trent Jr.

If Paul's company earns the standard 4% fee for negotiating contracts, that is a cool $17 million payday. Not bad for a kid who was selling throwback jerseys out of the trunk of his car when he met LeBron James.

More interesting from a how-the-sausages-are-made perspective, news-breakers made a concerted effort to prominently praise Paul like never before. Where once reporters cited anonymous sources without even mentioning agents, recent years have seen journalists directly attribute reports of new contracts to agents.

For example, Adrian Wojnarowski reported after the clock struck midnight ET Friday, "Tyrese Haliburton and the Indiana Pacers are agreed on a five-year, designated maximum contract extension that could be worth up to $260 million, his agents Dave Spahn and Aaron Mintz of [Creative Artists Agency Sports] tell ESPN."

When it came to Paul, though, he was a partner in the actual decision to agree.

"Draymond Green and CEO of Klutch Sports Rich Paul have agreed on a four-year, $100 million contract to return to the Golden State Warriors, sources tell The Athletic," Wojnarowski rival Shams Charania reported.

Same wording with Grant.

Likewise, Chris Haynes reported, "Forward Trey Lyles with CEO Rich Paul of Klutch Sports and agent Lucas Newton has reached an agreement to return to the Sacramento Kings, league sources tell NBA on TNT."

Same wording with Trent.

Following the same script, Broderick Turner of the Los Angeles Times reported, "Klutch Sports CEO Rich Paul and agent Josh Hairston have agreed to a multi-year deal for Cam Reddish to join the Lakers."

There is no question who the boss is: Rich Paul, Klutch Sports CEO.

Big wings

Are you 6-foot-6 and somewhere between a pretty bad and very good NBA player? Well, you just got paid.

Cameron Johnson, Kyle Kuzma and Grant — all high-quality wings who have been no better than the fourth- or fifth-most important member of a serious contender in their careers — earned a combined $370 million on Friday. Grant received $31 million more guaranteed than the next-highest earner on the market, and those three wings ranked among the seven-highest paid players on Day 1. The other four are All-Stars.

Wings are the most coveted asset in the modern NBA, but the theoretical ability alone to defend multiple positions and score over smaller defenders from all over the court is enough to make you a lot of money.

Julian Champagnie, who played 15 meaningless games for the Spurs after they claimed him off waivers in February, received a four-year, $12 million commitment from San Antonio. Cam Reddish, discarded by three teams in 17 months, got two years with a player option from the Los Angeles Lakers, who also gifted $51 million to Rui Hachimura — a player the Washington Wizards had no interest in paying a few months ago.

Caris LeVert and Georges Niang got a combined $58 million from the Cleveland Cavaliers, who also traded for Miami Heat guard Max Strus to presumably play more minutes than either of them on the wing.

Contrast them with Seth Curry, literally one of the most accurate shooters to ever live, who merely got the bi-annual exception from the Dallas Mavericks ... since he is 6-foot-2? Oh, to be only a few inches taller.

Joe Ingles, a 35-year-old one season removed from a torn ACL, who could not be played by the end of the Milwaukee Bucks' first-round playoff loss to the Heat, received $22 million over two years from the Orlando Magic. They are one of the few teams with salary-cap space, and he was their lone signing on Friday night.

It is good to be tall and maybe good in the NBA.

Tyrese Haliburton

Sure, the Indiana Pacers gave the 12th overall pick in the 2020 NBA Draft a maximum rookie-scale extension that could be worth $260 million, but more importantly it turns out Haliburton is good at memes.

LOSERS

Daryl Morey

The president of basketball operations for the Philadelphia 76ers waited months to trade one-time All-NBA guard Ben Simmons, sacrificing half the 2021-22 season in an effort to pair another star with Joel Embiid, and Morey made a show of welcoming James Harden off a private plane following the February 2022 trade.

Sixteen months later, Harden seeks a third trade in as many years, and the Sixers have done no more than hit the Eastern Conference semifinals ceiling they set before Morey's arrival. Harden is who we thought he was — a mercenary, a step slower and a level lower in the playoffs — not who Morey believed him to be.

Now, the Sixers face the prospect of turning Harden into a collection of salaries headlined by someone like ... Norman Powell from the Los Angeles Clippers? In trading Harden, Philadelphia may recoup the two first-round picks it packaged to get the one-time MVP, but the talent drain from who Simmons was at the time of the deal (a 25-year-old three-time All-Star) to whatever they will get for Harden is alarming, especially when you consider the Sacramento Kings offered Haliburton for Simmons, per Yahoo Sports' Jake Fischer.

(The Sixers also dealt Seth Curry in the trade for Harden. Curry was an exceptional complementary player for Embiid and just accepted a short-money deal from the Dallas Mavericks to help enhance Luka Dončić.)

Morey's fascination for a reunion with Harden, with whom he reached two Western Conference finals in their tenure together on the Houston Rockets, now runs the risk of alienating Embiid. The Sixers superstar just won the league's MVP award, and his team could be taking a significant step back in its quest to build a contender around him. Embiid has three years left on his contract with the Sixers, and the clock is ticking.

Boston's Eastern Conference challengers

Not only could the Sixers lose Harden, but the Milwaukee Bucks and Miami Heat might suffer, too.

The Rockets were expected to pursue Bucks center Brook Lopez at the start of free agency, and word came down Friday that their offer could exceed $40 million over two years. Losing Lopez — the runner-up for Defensive Player of the Year and a reliable stretch 5 — could cripple Milwaukee's championship hopes.

The Bucks also re-signed Khris Middleton for $102 million over the next three seasons, linking his timeline to that of Giannis Antetokounmpo. Middleton will turn 32 years old in August and has started just 19 of his team's last 92 games. That period includes a sprained left MCL, left wrist surgery and right knee surgery. The Bucks better be confident Middleton can return to his All-Star form, because if he is declining as a player at $34 million annually and the Bucks lose Lopez, Antetokounmpo may someday sour on Milwaukee.

Likewise, the reigning Eastern Conference champion Heat lost starting point guard Gabe Vincent to a three-year, $33 million contract with the Los Angeles Lakers. Fischer's report that the Cleveland Cavaliers were in the process of orchestrating a sign-and-trade deal for Heat wing Max Strus was met with this message from Miami's main man Jimmy Butler on Instagram: "Peace out." The writing was on the wall ... or his feed.

Miami managed to retain 34-year-old Kevin Love and reunite with Josh Richardson on Friday night, and the Heat are holding out hope that Damian Lillard requests a trade from the Portland Trail Blazers and pushes his way to South Beach. Miami also traded Victor Oladipo's $9.5 million expiring contract, creating a trade exception in that same amount that it could use to acquire more help. Still, losing two vital members of an already shallow playoff rotation might unsettle the close chemistry that carried the Heat to the NBA Finals.

Meanwhile, the Celtics reached an agreement with newly acquired one-time All-Star Kristaps Porziņģis on a two-year, $60 million contract extension that could keep him in Boston through the 2025-26 season. Celtics president of basketball operations Brad Stevens hopes a reliable third scoring option raises the ceiling of a team led by Jayson Tatum and Jaylen Brown, who have reached four conference finals together and the 2022 NBA Finals. That job may have gotten a little easier if the start of free of free agency is an indication.

Denver Nuggets

At their championship parade, Nuggets head coach Michael Malone informed the hundreds of thousands in attendance and millions more watching on television that Bruce Brown Jr. would re-sign in free agency.

"Y'all tell me, is Brucey B going anywhere? Hell no," Malone asked and answered. "Let’s run this s*** back."

Likewise, Brown told the crowd, "I've got one more question. One more year?"

It seemed as though Brown might follow the path Bobby Portis laid out after winning a title with the Milwaukee Bucks in 2021. Brown could re-sign with the Nuggets for no more than $7.8 million this season, and a handshake agreement could have guaranteed him a starting salary of more than $12 million in 2024.

Well, the Pacers were prepared to offer Brown a two-year, $45 million contract, and with a parade hangover in his rearview, he accepted within minutes of free agency opening, tripling his career earnings in one night.

Brown played an integral role in elevating the Nuggets to the NBA mountaintop, serving as a hard-working versatile defender and as an outlet for MVP Nikola Jokić both cutting to the rim and spacing to the 3-point line. His title-clinching put-back to end Game 4 of the NBA Finals was the perfect example of the brand of complementary basketball he has shown in the playoffs for both the Nuggets and Brooklyn Nets.

The Nuggets hope second-year wing Christian Braun assumes some of the 26.5 minutes per game Brown played in the postseason, but they do run the risk of losing the difference between contender and favorite.