Hindsight is 20/20, which means we now have perfect vision to go back and grade some of the most lucrative and momentous NBA signings of the past 20 years.
Deals that were renowned for their incredible dollar amount, the prestige of the player and the following historical significance were all considered. The player also had to be an unrestricted free agent and not simply signing a contract extension.
Since it takes some time to accurately place a grade, all signings that occurred less than a year ago (Kevin Durant, Kawhi Leonard, Kyrie Irving, Jimmy Butler, Kemba Walker, etc.) will not be included.
With the benefit of time, here's how the 10 biggest deals of the past 20 years grade out.
Michael Jordan Unretires Again, Signs with Wizards (2001)
Contract Details: Two years, $2 million
While the money alone doesn't make this one of the most lucrative contracts, Jordan returning to the NBA after a three-year retirement was a huge deal at the time.
Jordan, then 38, first had to sell his ownership stakes in the Washington Wizards and Capitals, then he announced he would be donating his first-year salary of $1 million to the victims of 9/11.
From a pure production standpoint, few players (if any) could be out of the NBA for three full seasons before returning in their late 30s and posting the kinds of numbers Jordan did. In two seasons, he averaged 21.2 points, 5.9 rebounds, 4.4 assists and 1.5 steals, all while logging 36.1 minutes per game.
The Wizards, however, were still pretty bad.
Kwame Brown flopped as a No. 1 overall pick, a young Rip Hamilton was traded to the Detroit Pistons for veteran Jerry Stackhouse (who wished he had never played with Jordan in Washington), and the Wizards won just 37 games both seasons.
It wasn't a complete disaster, however, since Washington's attendance jumped from 18th in 2000-01 to second in the NBA while Jordan played.
Given how small his contract was, plus the revenue he generated, this was neither a complete success nor a complete failure.
Updated Grade: C
Steve Nash Returns to Phoenix Suns (2004)
Contract Details: Five years, $65 million
Nash was already a two-time All-Star before he signed with the Suns, but he became a Hall of Famer in Phoenix.
Leaving a Dallas Mavericks team that had Dirk Nowitzki, Michael Finley and Josh Howard wasn't an easy decision, especially since the Mavs had just won 52 games while Phoenix was coming off a 29-win season.
Nash's first assist with the Suns actually came before he put on a uniform, though, as he took less money so Quentin Richardson could also sign in Phoenix.
Over the course of the five-year contract, Nash led the NBA in assists three times, was a four-time All-Star and won back-to-back MVP awards in 2004-05 and 2005-06. His strong play resulted in a pair of trips to the Western Conference Finals, 26 playoffs victories and the ignition of the pace-and-space concepts that nearly every NBA team uses today.
In terms of pure value, few contracts have been better than this.
Updated Grade: A
Gilbert Arenas Takes Discount with $111 Million Deal (2008)
Contract Details: Six years, $111 million
Gilbert Arenas became an unrestricted free agent by opting out of the final season of his six-year, $65 million contract, stating at the time that he wanted to sign a max deal.
In the four years leading up to his free agency, Arenas was a three-time All-Star who averaged 27.3 points, 4.2 rebounds, 5.7 assists and 1.9 steals while shooting 35.8 percent from three and playing 40.6 minutes per game. A long-range shooter who would have fit perfectly in today's NBA, Arenas was one of the league's best players at the time, even making three All-NBA teams.
Washington actually offered Arenas more money at the time with a full six-year, $127 million max deal on the table. Arenas voluntarily took less in order to help keep talent around him, and the Wizards used the funds to sign Antawn Jamison to a four-year, $50 million deal.
Unfortunately, knee surgeries began to pile up for Arenas.
He played just two games in 2008-09 and would only last four total seasons in the NBA after signing the six-year deal, bouncing from the Wizards to the Orlando Magic and Memphis Grizzlies.
While a healthy Arenas would have been worth the $111 million (or even the full $127 million), his knees ultimately made this one of the worst contracts in the NBA.
Updated Grade: F
Chris Bosh Leaves Raptors for Heat (2010)
Contract Details: Six years, $110.1 million
While LeBron James deservedly gets the most recognition for leaving the franchise that drafted him to join the powerhouse Miami Heat, the signing of Chris Bosh was a landmark move on its own. He agreed to leave the Toronto Raptors and team up with Dwyane Wade and an incoming James, a move that dropped his previous organization from 40 wins in 2009-10 to just 22 the following year.
The No. 4 overall pick by Toronto in 2003, Bosh was a five-time All-Star during his seven years with the Raptors, averaging 20.2 points, 9.4 rebounds, 2.2 assists and 1.2 blocks.
Miami was coming off a 47-win season and a playoff appearance, and adding Bosh to Wade and the incumbent core would likely have created a top-four team in the East even without James. Under this deal, which ended up lasting four years due to a 2014 opt-out, the Miami Heat won two titles and made four trips to the NBA Finals behind their Big Three. Bosh was a four-time All-Star.
While it was undoubtedly a successful signing, the fact that Miami gave up two first-round picks so that Bosh could agree to a longer sign-and-trade and still saw him opt out after four years knocks the final grade down a bit.
Updated Grade: B+
LeBron James to Heat, Cavaliers and Lakers (2010, 2014, 2018)
Contract Details: Six years, $110.1 million with Miami; Two years, $42.1 million with Cleveland; Four years, $154 million with Los Angeles
LeBron James' free agencies have been some of the most fascinating NBA storylines of the past 20 years.
Starting with The Decision in 2010, James was in his athletic prime as a 25-year-old joining the Miami Heat. Like Chris Bosh, he took less than a full max deal through a sign-and-trade that made Miami give up two first-round picks to the Cleveland Cavaliers. Other than that, the deal was phenomenal for the Heat.
James' four years in Miami resulted in four trips to the Finals, two championships, two regular-season MVPs and two Finals MVPs. In 294 regular-season games, he averaged 26.9 points, 7.6 rebounds and 6.7 assists.
Coming back to Cleveland in 2014, James initially signed a two-year deal with an opt out in the second season to capitalize on the rapidly rising salary cap. Like his four years in Miami, James led the Cavs to four straight NBA Finals, this time winning one title and a Finals MVP. He averaged 26.1 points, 7.7 rebounds and 8.0 assists and was instrumental in getting Kevin Love to agree to a trade and ultimately re-sign in Cleveland.
His decision to leave the Cavaliers for a second time, this time to sign with the Los Angeles Lakers, is far tougher to grade.
His first season in L.A. was a disaster as he played in a career-low 55 games and missed the postseason for the first time since 2005. While it certainly wasn't James' fault the Lakers were that bad, failing to make the playoffs after eight straight years in the Finals was a shock.
This season has started far better, with James leading the Lakers to a Western Conference-best 49-14 record before the campaign was suspended due to the coronavirus pandemic. He leads the NBA with 10.6 assists per game in his age-34 season and has put up 26.5 points, 8.2 rebounds and 9.5 assists per game in 115 appearances with Los Angeles over the two relevant years.
While he hasn't earned a title (yet?) with his newest team, signing James anywhere is guaranteed to earn an A of some kind.
Updated Grades: A+ for Miami; A+ for Cleveland; A for Los Angeles
Dwight Howard Leaves Lakers for Rockets (2013)
Contract Details: Four years, $88 million
Even after his failed year with the Los Angeles Lakers, it was still surprising to see Dwight Howard leave $30 million on the table by turning down a five-year, $118 million contract to return to L.A.
Joining the Rockets meant far less guaranteed money, but also the opportunity to form a duo with then-24-year-old James Harden. Harden had spent just one year in Houston at the time, averaging 25.9 points and 5.8 assists.
While Harden was a notoriously terrible defender, Howard was a three-time Defensive Player of the Year who the Rockets hoped would help cover up any mistakes made on the perimeter. But even though he made the All-Star team during his first season in Houston, the big man was never the same player who dominated for the Orlando Magic.
His time with the Rockets lasted just three seasons, with Houston getting knocked out in the first round of the playoffs twice. Howard didn't even finish his four-year contract, choosing to opt out after Year 3 to sign with the Atlanta Hawks.
While he continued to put up numbers (16.0 points, 11.7 rebounds, 1.6 blocks in 32.2 minutes per game), this wasn't the dominant Howard that Houston expected when it signed him to a massive deal.
Updated Grade: C+
Carmelo Anthony Turns Down Bulls for Knicks (2014)
Contract Details: Five years, $124 million
While he ultimately settled on a near-max deal with the New York Knicks, Anthony was almost a Chicago Bull.
He detailed his plans on ESPN's First Take in 2009:
"I was going to Chicago. Derrick Rose, Joakim Noah, I was there, right? I was there. And then I started getting whispers behind the scenes. Yo, look, this person ain't gonna be there. It ain't really right. This and that. It was all of that started to come up in the midst of my decision-making. I wasn't gonna let anything cloud that. I met with New York last. Like, I think it was the last team I met with because I knew that I was ready to move on from that situation because of what I was dealing with and going through in New York."
Anthony was 30 and still hanging on to the prime of his career. He had led the league in scoring just two years earlier and was coming off a season in which he averaged 27.4 points, 8.1 rebounds, 3.1 assists and 1.2 steals.
The Knicks had won just 37 games, however, and needed Anthony to have any chance at making the playoffs.
After agreeing to a five-year deal, Anthony lasted just three more seasons with the Knicks before he was traded to the Oklahoma City Thunder for Enes Kanter, Doug McDermott and a 2018 second-round pick that would later become Mitchell Robinson.
Not wanting to pay him the final $26.2 million on his contract, OKC traded Anthony, along with a first-round pick, to the Atlanta Hawks for Dennis Schroder in a three-team deal after just one season. He would never play a game for Atlanta, which ate the majority of the final part of his $124 million deal before waiving him.
While the Knicks got three All-Star seasons out of Anthony on this contract, they never made the postseason and got little back for him in return. For someone on a $100 million-plus deal, that was a bitter disappointment.
Updated Grade: C-
Kevin Durant Jumps on Warriors 73-Win Team (2016)
Contract Details: Two years, $54.3 million
In what's perhaps the most shocking signing of the past 10 years, Kevin Durant's decision to leave the Oklahoma City Thunder for the 73-win Golden State Warriors forever altered the course of NBA history.
Like LeBron James signing with the Cleveland Cavaliers in 2014, Durant opted to choose smaller deals to maximize his earnings with an ever-rising salary cap. The 2016 spike in cap space, coupled with Stephen Curry still playing on a modest contract signed after continuous ankle injuries, allowed the Warriors to open up enough room to sign Durant. Any other summer, this wouldn't have been possible.
Despite initially signing a two-year deal with an opt-out clause, Durant's time in Golden State ultimately lasted three seasons. For about 99 percent of the time, it couldn't have gone any better.
Durant won two Finals MVPs and led Golden State to two championships and three Finals appearances while averaging 25.8 points, 7.1 rebounds, 5.4 assists and 1.5 blocks over 208 regular-season games.
A calf strain suffered against the Houston Rockets in the 2019 playoffs and a ruptured Achilles in the 2019 NBA Finals ultimately ended what could have been a three-peat, and Durant left the Warriors for the Brooklyn Nets last summer.
If not for the injuries that cost him his ability to help deliver a third title, this would have been an A-plus signing.
Updated Grade: A
Blake Griffin Picks Clippers over Suns, Nuggets (2017)
Contract Details: Five years, $173 million
Blake Griffin's deal with the Los Angeles Clippers will be forever pointed to as an example of why players need not be loyal to their teams.
A five-time All-Star in Los Angeles and the leading scorer on what became the most successful run in franchise history, Griffin chose to re-sign with the Clippers in 2017 after initially scheduling meetings with the Phoenix Suns and Denver Nuggets.
His five-year, $173 million contract was far more than the four-year, $130 million deal all other teams could have given him. While it was overly celebrated at the time with comparisons to Martin Luther King Jr., Albert Einstein, Gandhi and others, his time in L.A. wouldn't last long.
Just 33 games into his five-year contract, the Clippers traded him to the Detroit Pistons for a package that included Tobias Harris, Avery Bradley and a first-round pick. Harris would later be traded to the Philadelphia 76ers for a pair of firsts that were ultimately used to help acquire Paul George (and Kawhi Leonard).
Griffin was great for Detroit last season, earning an All-Star appearance while helping lead the Pistons to the eighth seed in the Eastern Conference playoffs. This year, a knee injury has limited him to just 18 games.
With two years and $75.6 million still on his contract, Griffin's deal has become one of the worst in the NBA.
Updated Grade: D+
Stephen Curry Signs NBA's First $200 Million Deal (2017)
Contract Details: Five years, $201 million
Curry's supermax signaled the first $200 million contract in the NBA, a number that will pay him $45.8 million in the final year.
The deal was a no-brainer at the time. Curry was a two-time MVP, a four-time All-Star and a two-time NBA champion who had spent his entire career with Golden State. He was one of the most beloved players in the league, and keeping him meant keeping the Warriors' budding dynasty alive.
While the Warriors certainly don't regret the deal, Curry has struggled to stay healthy since signing it.
The 32-year-old has played in just 125 of a possible 229 games (54.6 percent) since signing the deal, although his time on the court has resulted in averages of 26.6 points, 5.2 rebounds and 5.6 assists with a 42.5 percent success rate from three. Golden State also won the 2018 title behind the help of its point guard.
With the Warriors an NBA-worst 15-50 this season, Curry can finish the contract strong by helping lead Golden State back to the playoffs again next year with a healthy Klay Thompson and Draymond Green once again by his side.
Handing him a $200 million deal remains the right choice, but Curry's injuries have prevented him from living up to it so far.
Updated Grade: B
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