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2021 NBA free agency: Winners and losers from Day 1, starring Pat Riley's Miami Heat

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NBA free agency opened on Monday, and more than 50 deals were made before the clock struck midnight, including most of the top names expected to change teams, if not all of them. Plenty of transactions are left to be made, but here we highlight the biggest winners and losers from the wild first day of free agency.

WINNERS

Pat Riley and the Miami Heat

The Miami Heat's team president did the bulk of his impressive work in the first 39 minutes after free agency opened at 6 p.m. ET on Monday. In that span, Riley acquired Kyle Lowry from the Toronto Raptors, extended Jimmy Butler's maximum contract and re-signed sharpshooter Duncan Robinson, remolding a roster he hopes will deliver his 11th championship in almost 50 years as a player, coach and executive. 

If Riley's slicked-back hair had a cap, he might tip it to the league office for bumping up the start of free agency from midnight, because the 76-year-old also had plenty of time to swipe P.J. Tucker from the Milwaukee Bucks and re-sign a few more of their own fringe free agents before calling it an early night.

We can debate whether a roster constructed around Lowry, Butler and Bam Adebayo will be good enough to unseat the Bucks from their throne or compete with the Brooklyn Nets in the Eastern Conference, but the Heat secured Lowry, the best player to change teams on Monday, and stole Tucker from a budding rival.

It remains to be seen whether Lowry is a worthwhile upgrade over the assets Miami reportedly sent to the Toronto Raptors to complete the sign-and-trade deal (Goran Dragic, Precious Achiuwa and a second-round pick) for three years and $90 million. On paper, Lowry is an upgrade to a core that reached the 2020 Finals. Riley has at the very least propped open a three-year window for Heat culture to squeeze a championship contender out of a robust rotation that features Robinson, Tucker and Tyler Herro around an All-Star trio.

Old point guards

Chris Paul's success with the Phoenix Suns this past season earned him a four-year, $120 million contract from the Western Conference champions that will take him through his 40th birthday. It also helped Lowry land a contract that will pay him roughly $30 million at age 38. The Heat surely saw similar attributes in Lowry to the leadership, cunning and talent that Paul leveraged to elevate the Suns to unforeseen heights.

The list of point guards to average base levels of 13 points and seven assists per game in their age-36 season or beyond is a short one: Steve Nash in 2010-11, John Stockton in 2001-02 and Lenny Wilkens in 1973-74. Two of them failed to make the playoffs, and the third (Stockton) lost in the first round. Stockton and Wilkens retired within a year, and Nash's health fell into steep decline starting in the 2011-12 season.

The Heat and Suns are respectively asking so much more from Lowry and Paul, who are being paid to play and lead at an All-Star level on both ends of the floor deep into the playoffs. Both exceeded 16 points and seven assists per game on high efficiency in star-caliber performances this past season at ages 34 and 35. Lowry missed 26 games for the tanking Raptors, and Paul limped to the finish line in a six-game Finals loss.

Nash's last deal with the Suns was a two-year, $22 million extension that paid him 20% of the salary cap at age 37 and expired as he made his final All-Star appearance in an injury-plagued 2011-12 campaign. Lowry and Paul will earn roughly 25% of the projected $119 million salary cap in the second year of the deals they just agreed to sign, which extend beyond next year and through their 38th and 40th birthdays, respectively.

When all was said and done on Monday, no free agents came within $5 million of the $30 million average annual salaries Lowry and Paul received. Only 10 players over age 31 reached agreements on the opening night of free agency. The two others to warrant more than two years at a rate of $10 million annually were point guards: 2021 All-Star Mike Conley (three years, $72.5 million) and one-time MVP Derrick Rose (three years, $43 million). The next highest-paid among them was 32-year-old JaMychal Green (two years, $17 million).

The Class of 2018

Within moments of the negotiating window for rookie contract extensions opening at midnight, Trae Young and Shai Gilgeous-Alexander officially had their five-year, $172 million maximum deals on the table. Those offers can climb to $207 million if either makes one of the three All-NBA teams this coming season. Fellow 2018 draftee and two-time First Team All-NBA selection Luka Doncic will be locked into that larger figure once he returns from leading Slovenia at the Tokyo Olympics, according to Marc Stein and his Substack.

The No. 1 overall pick in their class, Deandre Ayton, is likely to follow soon with a max extension from the Suns. In the coming days and weeks, there is still plenty of high-priced business to negotiate on long-term extensions with established 2018 first-round draft selections Michael Porter Jr., Jaren Jackson Jr., Mikal Bridges, Collin Sexton, Kevin Huerter, Robert Williams III and Miles Bridges, among a few others.

Second-round 2018 draftees Devonte Graham and Gary Trent Jr., both restricted free agents, were two of only 13 players to earn more than $45 million on Monday. Graham's deal is worth a reported $47 million over four years from the New Orleans Pelicans, and Trent got $54 million over three years from the Toronto Raptors. Second-round classmate Bruce Brown accepted a $4.7 million discount rate from the Nets, while Jalen Brunson and Mitchell Robinson — the 33rd and 36th overall picks — are eligible for extensions.

The Heat's $90 million commitment to 2018 University of Michigan alum Duncan Robinson marked the highest ever for an undrafted free agent. That pushed the combined earnings for the NBA's Class of 2018 on the first night of free agency north of $750 million. They are sure to hit the $1 billion mark in short order.

Kyle Lowry and Jimmy Butler last were teammates at the 2020 NBA All-Star Game. (Stacy Revere/Getty Images)
Kyle Lowry and Jimmy Butler last were teammates at the 2020 NBA All-Star Game. (Stacy Revere/Getty Images)

LOSERS

Rule followers

On the eve of free agency, ESPN's Adrian Wojnarowski outlined the framework of the sign-and-trade deal that would send Lowry to Miami for Dragic and Achiuwa. The moment free agency opened on Monday, Yahoo Sports' Vincent Goodwill indeed reported that all parties were in lockstep on that same agreement.

None of the business of negotiating whether Lowry wanted to leave the Raptors, for what price and at what return was allowed under NBA rules until 6 p.m. ET on Monday, and it was all done before the bell rang for a sixth time. The Heat undoubtedly tampered to land the best available free agent on the market, and there has not been one word from the league office, because this is how business is conducted every offseason.

Likewise, the Chicago Bulls purportedly reached agreement on a four-year, $85 million contract with Lonzo Ball and negotiated his sign-and-trade deal with the New Orleans Pelicans for Tomas Satoransky, Garrett Temple and a second-round pick before the clock hit 6:01 p.m. Lightning-quick work, we are led to believe.

The NBA fined the Milwaukee Bucks a 2022 second-round pick this past December, when word leaked that the Bucks had reached a sign-and-trade agreement to acquire Bogdan Bogdanovic from the Sacramento Kings before the start of free agency. If only the Bucks had waited until the second free agency opened to share news of the handshake agreement, they might have landed Bogdanovic or at least still have that pick.

Let this be yet another lesson to everyone that if you are not breaking the rules, you are not properly general managing your NBA team, and it is all OK if you just allow the league to pretend it takes seconds for agents to survey the entire landscape of the league, negotiate the length and value of a contract from their client's desired destination and allow time for two teams to reach terms on fair trade compensation.

Zion Williamson and the New Orleans Pelicans

The Pelicans' acquisition of Graham for a low eight-figure rate was a good one, but it was a last resort.

New Orleans executive David Griffin dropped seven spots in the first round of this year's draft and dealt a protected first-round pick from the Los Angeles Lakers to unload the cumbersome contracts of Steven Adams and Eric Bledsoe on the Memphis Grizzlies. In return, the Pelicans received the expiring contract of quality center Jonas Valanciunas and what amounted to max salary cap space for spending this summer.

Griffin was linked in various reports to Chris Paul, Kyle Lowry, Reggie Jackson and Spencer Dinwiddie, all more proven contributors (particularly in the playoffs) than Graham, who cost the Pelicans their own lottery-protected first-round pick next season. Here's the thing, though: They could have just re-signed Ball.

Honestly, would you rather have Graham, Satoransky, Temple and a second-round pick for roughly $60 million or Ball for $85 million and a first-round pick? The Pelicans also could have had Ball and Graham, solidifying their point guard rotation for the next four years around Zion Williamson and Brandon Ingram.

The most plausible reason for not matching Ball's contract has to be that Ball would have been unhappy in New Orleans, no matter how much he said at the end of last regular season, "I would love to be back." The 23-year-old had multiple serious suitors in restricted free agency, including the Boston Celtics and Dallas Mavericks, and his value as an asset will only rise if he shows continued signs of two-way improvement.

It is not a great look to lose Ball and your best possible replacements, while also failing to even generate interest from a big name as one of the few teams with significant cap space. It is the look of a small-market team operating at less than all cylinders. Ball's decision to leave Williamson and Ingram after two seasons is not exactly a ringing endorsement of their ability to lure potential stars with future cap space, either. 

Mark Cuban and the Dallas Mavericks

The billionaire owner of the Mavericks is eager to spend on a championship contender around Doncic, but nobody ever wants to come to Dallas, the NBA's fifth-largest media market, complete with warm weather, no state income taxes and state-of-the-art team facilities. The Mavericks' greatest-ever free-agent signings are not an inspiring bunch and might feature J.J. Barea in the top five. Superstars often leave Dallas off their list of meetings, and stars like DeAndre Jordan and Dwight Howard have memorably spurned Cuban.

The Mavericks entered this year's free-agency period with max cap space, reportedly targeting Lowry to fill a second playmaking role alongside Doncic. They were ruled out before they ever had a chance to make an official pitch. Instead, they re-signed Tim Hardaway Jr. for $74 million over four years and brought back Boban Marjanovic on short money — both deals they theoretically could have made with Lowry in the fold.

Their biggest acquisitions on the first night of free agency were Reggie Bullock (three years, $30.5 million deal) and Sterling Brown (two years, $6.2 million). If new general manager Nico Harrison's previous relationships as a Nike executive were supposed to be a big factor in his hire, they failed him in his first time of NBA need.

Once Doncic's extension kicks in, the Mavericks will have more than $100 million committed to him, Kristaps Porzingis, Hardaway and Bullock in the 2023-24 season, meaning the Mavericks may not see max cap space again for a few more years. They also owe their 2023 first-round pick to the New York Knicks from the Porzingis fallout, making big-name trade acquisitions all the more difficult in the meantime.

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Ben Rohrbach is a staff writer for Yahoo Sports. Have a tip? Email him at rohrbach_ben@yahoo.com or follow him on Twitter! Follow @brohrbach

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