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Free agency is always a trip. The year 2020 gave us a very windy, unexpected free agency trip.

The NBA’s November free agency period has been as surprising as the year it fell under.

Gordon Hayward shocked the NBA world by securing a bag that no one thought was possible for him. The Atlanta Hawks stacked their bench with highly-priced aged veterans. The Oklahoma City Thunder and New Orleans Pelicans engaged in a draft pick Verzuz battle.

While free agency is still very active with plenty of players still available, there are clear winners and losers of the 2020 free agency so far.

Let’s dive in below.

Winner: Portland Trail Blazers

It wasn’t that long ago when a Damian Lillard-led Portland Trail Blazers team was swept in the 2019 NBA Western Conference Finals. They followed that appearance by struggling to make the playoffs the following season. Attempting to get back into the Western Conference chase, the Blazers made very strong additions to their roster. 

The key success the Blazers had during free agency was keeping their core – CJ McCollum and Damian Lillard. After failing to get over the playoff hump, many teams will look to “blowing up” the roster. Take a look at Houston for example. Portland resisted the tempting urge of heading into a new direction and instead added much-needed wing depth.

Adding wing defender Robert Covington via a trade with the Houston Rockets filled a major team need. With the Western Conference being guard-heavy, adding a key defender to guard the perimeter was essential. It may be impossible to fully stop certain key guys, but containing them is an option. And up until now, the Blazers haven’t had anyone who can fulfill that option. Covington checks that box while also being a three-point threat.

The Blazers also added Derrick Jones Jr. Jones, 23, is an athletic young option for Portland to use as either a starting small forward or a member off the bench. Retaining Carmelo Anthony on a minimum deal is another strong move that keeps the locker room balanced and provides a reliable scoring threat down the stretch. 

Down low the Blazers brought back fan-favorite Enes Kanter, who played extremely well for Portland during their 2019 playoff run. They also took a chance on 22-year-old former King Harry Giles III.

The Blazers added needed depth without compromising what already works for them.

Loser: Boston Celtics

Gordon Hayward’s reintegration into the starting lineup was a locker room diver in 2019. The decision to place Hayward back into his original role after his leg injury is believed to be the final straw that pushed Kyrie Irving and Al Horford away. One year later, Hayward is also gone.

This move comes as a major shock to Boston. When the Celtics and Hayward mutually agreed to move Hayward’s option deadline back, it appeared they were treading in the right direction, leading to either a long-term deal or a sign and trade. 

Instead, the Celtics are left to watch another pricey star walk away as an unrestricted free agent without receiving anything in return except for memories. Hayward’s departure takes 17.5 points, 6.7 rebounds, and 4.1 assists per game on a 50.0 percent shooting away from the Celtics. The 2020 playoffs showed that the Celtics are in need for consistent scoring down the stretch, something that they did not acquire in November.

Winner: Fred VanVleet

Fred VanVleet’s NBA career started with him not being called during the NBA Draft, seemingly unwanted by all 30 teams. Instead of quitting, VanVleet decided to work even harder to find himself a place in the NBA. He spent most of his rookie years with the Toronto Raptors’ G-League affiliate, before being called up to play for the Raptors due to injuries. 

VanVleet had a breakout run with the Raptors and is now on a full contract with the team, securing a major extension that will last the next four years. His $85 million deal is the second-largest to date of any 2020 free agent. It’s also the biggest contract ever signed by an undrafted player.

Loser: Michael Jordan

Michel Jordan gets his name dragged around on social media daily by users who never got to see him play a live game. If that isn’t enough to feel a little bit of sympathy for MJ, then the money he has to fork out this year should invoke Hamilton’s “It’s Quiet Uptown” vibes.

The Hornets desperately needed a post. After adding LaMelo Ball to a roster that includes P.J. Washington, Miles Bridges and Devonte’ Graham, they needed a pick and roll big who could clean up the boards and free up more space for ball handlers. The ideal candidates for that position would’ve been Montrezl Harrell or Serge Ibaka.

Charlotte missed out on both bigs. Somehow, someway, that led the Hornets – the team MJ owns – to Gordon Hayward.

Hayward signed a four-year, $120 million deal with the Hornets, inking possibly the worst contract of this free agency class. This signing not only fills Charlotte’s salary space but also doesn’t guarantee a playoff spot.

Hayward’s style of play, which is a system-made slower tempo, doesn’t match the fast pace style of his new teammates. He doesn’t fill defensive needs nor rebounding holes within the roster. Most importantly, he’s going to take reps away from the young players who need to develop.

There are more potential negatives than positives, and MJ is going to front the bill of the more than likely negative outcomes for the next four years.

Winner: Los Angeles Basketball

The Lakers and Clippers have developed into one of the more fascinating one-sided rivalries in current sports. While the Lakers have 17 championships to the Clippers zero, the city feels that there is a bit of a competition among the two teams who share an arena.

That competition only heated up when the Lakers signed Sixth Man of the Year Montrezl Harrell and SMPOY runner up Dennis Schroder, along with Wesley Mathews and Marc Gasol. Schroder is coming off a career year with the Oklahoma City Thunder, while Matthews is a respected vet. Gasol recently won a championship with the Toronto Raptors, playing an essential role defensively in the paint and offensively on the perimeter.

The best part of the Lakers signing is Harrell, the former Clipper. Harrell won SMPOY with the Clippers having a breakout season before crashing in the NBA Bubble. Harrell’s signing came as a shock to many, including Clipper players. Fans had a field day with the signing, many finding old tweets of Harrell dissing the Lakers. 

While the Lakers got better, the Clippers got better too. The Clippers managed to resign wing defender Marcus Morris and add Serge Ibaka to their roster, a longer more defensive-minded big man. Ibaka is better suited to defend Anthony Davis and Nikola Jokic, two regards that Harrell was inadequate in. 

The “battle for LA” is going to be fun. The city caught a dub during free agency.

Loser: Houston Rockets

The city of Houston has been through enough on the baseball side. They didn’t need basketball woes as well. Once reports broke that their former MVP James Harden wanted out, the levees of Houston basketball seemed to have broken, and a biblical flood serged through the Rockets organization.

The cracks began when both Mike D’Antoni and Daryl Morrey walked for nothing. Following their departure came reports of Harden’s disdain for the organization. Then the reports of Harden wishing to play with Kevin Durant and Kyrie Irving in Brooklyn surfaced. Finally, it was reported that Harden requested a trade after declining a contract that would’ve given him nearly $51-million a year.

From there, former MVP Russell Westbrook, PJ Tucker and Eric Gordon requested a trade, while Austin Rivers left for the Knicks.

Darly Morrey moved into the Philadelphia 76ers organization, creating a very good roster. D’Antoni joined Steve Nash’s bench in Brooklyn, the destination Harden is dreaming of. Currently, Houston is trying to trade Westbrook and Harden – finding no luck in negotiations. 

If Paul George and Anthony Davis taught NBA front offices one thing, it is that a disgruntled star can ruin a season. Two disgruntled stars? Well, in the words of Teddy Duncan, “Good luck.”

Winner: Gordon Hayward

Love for the game is nice and all, but money talks a different language. Currently, Gordon Hayward has unlocked every level in cash flow Duolingo.

The 30-year old one-time All-Star recently secured a contract that will pay him $30-million a year. Hayward’s deal is set to last past his 34th birthday. Prior to his 30th birthday, Hayward had the following happen:

  • Hayward has missed 111 regular-season games and 31 playoff games. 
  • His per-game numbers have declined on a deeper Boston roster, and his efficiency hasn’t necessarily improved either with less defensive attention. Hayward’s true shooting percentage last season was 59.5 percent, the same number he posted in his final Utah season. 
  • This goes without saying, but he has aged three years. 

Despite these facts, the player is never at fault for taking money. The organization that decided a player’s game is worth the bill is responsible for that decision. Lou Deng is a perfect example of this. Hayward is now the only person who can say they beat a full-strength Michel Jordan.

Loser: Milwaukee Bucks

The Milwaukee Bucks are currently competing in the league’s highest viewed dating reality show. They are trying to win the love of their superstar, Giannis Antetokounmpo. Currently, it doesn’t look like they’re going to get a rose.

After an early playoff exit, rumors swirled that Antetokounmpo will leave the Bucks in the 2021 free agency period. The Bucks’ front office held a meeting with Antetokopunmpo, promising to strengthen the roster.

And it appeared as though they were going to do just that. They traded Eric Bledsoe, George Hill and three draft picks for Jrue Holiday – a slight upgrade at the point guard slot.

The biggest move, one that makes the Holiday trade worthwhile, was the sign and trade of Bogdan Bogdanovic. Antetokounmpo highly respects Bogdanovic and wanted to play with him. Holiday’s passing and defense would’ve matched beautifully with Bogdonivic.

The only problem is that Bogdanovic didn’t want to come to Milwaukee. The Athletic reported that the deal was in danger of falling apart because Bogdanovic had not agreed to sign a new deal with the Bucks.

Instead, Bogdanovic signed with the Atlanta Hawks, a team that hasn’t been close to sniffing the playoffs since 2015. The Bucks, a contender, were unable to recruit a young star to play with the reigning MVP. 

That does not help them get a rose.

On top of that, the league is now investigating the Bucks for possible tampering violations.

Again, not how you get a rose.

Winner: Adam Silver

It is no secret that the league’s number dipped during the 2019-20 season, especially during the pandemic. The current COVID-19 guidelines will place heavy restrictions on teams in markets that have high COVID-19 rates. This will lead to high losses in basketball-related income, a decline that hurts the league.

This leaves the league banking on high viewership. Player mobility brings in attention. Casual fans enjoy the banter of narratives that are caused by movement. Harrell leaving the Clippers for the Lakers, Hayward teaming up with Ball, and Antetokounmpo’s Golden State-Miluwakee love triangle are all narratives that bring in viewership because they are issues of human interest.

These types of free agency periods only help the league’s number, which in turn, makes Silver’s job a whole lot easier.