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Giannis, Damian Lillard, and the Need to Win Now in the NBA

Milwaukee pushed all of its chips to the middle of the table to acquire the Blazers star, showing a commitment to winning today at the expense of the future. A tactic that has become more and more common in modern American sports

It has been nearly 4 months since All-Star point guard Damian Lillard requested a trade from the Portland Trail Blazers. The saga that followed was filled with presumptions that the Miami Heat would land Lillard (as that was his preferred destination) and with many words being written and said about the demise of loyalty in professional sports. This week, the saga ended with a somewhat surprising destination. Damian Lillard after 11 seasons in Portland is now a Milwaukee Buck. The trade involved the Blazers, Bucks, and Phoenix Suns to get done with some notable names changing zip codes. Jrue Holiday and DeAndre Ayton are re-routed to Portland while Jusuf Nurkic, Grayson Allen, and Nassir Little are headed to Phoenix. The Blazers also get draft assets in the deal.


And while many will spend the coming days and perhaps weeks reminiscing on Lillard's time in the City of Roses (as was evidenced in this piece by Chris Haynes) and theorizing what will become of Jrue Holiday’s future, the real story here is the proactive nature of the Bucks to identify a star player and go after him. What the Bucks have shown is that a small market team can stay aggressive to keep their star player. The Bucks saw the writing on the wall from Giannis Antetokounmpo and acted, where they very easily could have played the blame game. And for that they need to be commended.


The Wishes of a Star Player


This summer Giannis Antetokounmpo drew a line in the sand with the Milwaukee Bucks. Giannis, a player that has been characterized as a throwback superstar that has never been associated with the player empowerment movement, spoke up. With a contract extension on the horizon, Antetokounmpo made it clear to the Bucks that he would not sign until it became clear that the team was going to continue competing for a championship.


It is a fair concern from Giannis, when one considers where he is in his career. Here is a player that is still firmly in his prime as he approaches his 29th birthday. He is at the peak of his powers, coming off of his first 30+ point per game campaign, having amassed virtually any accolade that an NBA player could want. He is an NBA champion, 7-time All-Star & All-NBA selection, a 5-time All-Defense selection, 1-time Defensive Player of the Year, and a 2-time League MVP. If he retired today, he is likely already a Hall of Fame player (Antetokounmpo has a 94% Hall of Fame probability according to Basketball Reference).


So at this point, Giannis is in the winning stage of his career. He has achieved all the personal accolades that any player could want. All that remains is contending for championships annually while he is still a top 3 player in basketball. The Bucks recognized this trajectory a few years ago, which led them to acquire Jrue Holiday from the New Orleans Pelicans in 2020. This trade sent out future draft picks and solid rotation players Eric Bledsoe and George Hill with the goal of winning now and worrying about the future later.


The move paid off and resulted in the Bucks first championship since the days of Kareem Abdul-Jabbar (who went by Lew Alcindor at the time) and Oscar Robertson. But eventually, every “win now” move has a price to be paid and the Bucks were approaching that moment this off-season. While Giannis was in his prime, most of his teammates were not. The Bucks were the league's oldest team and starting to show signs of degradation. Holiday specifically saw a drop-off in efficiency in the playoffs going from 49% from the field and 39% from three in the regular season, to 39% from the field and 30% from three in the playoffs as a Buck. To keep competing for championships and to keep Giannis happy, a change needed to be made. And that change has come in the way of Damian Lillard.


Dame Time in the Cream City


Damian Lillard has never had a co-star quite like Giannis Antetokounmpo, and it can be argued that Giannis has never had a big shot maker on his team of Damian Lillard’s stature. Lillard’s tenure with the Trail Blazers was iconic, and Lillard is arguably one of the best three players to ever put on the team's uniform. It is also incredibly likely that when he retires, his number 0 will be retired in the rafters of the Moda Center. Lillard wanted to make it work in Portland, but a combination of injuries and missed opportunities in player acquisition have left Lillard with only one Conference Finals appearance.


He now joins a team that is ready to win and compete for championships. One with the depth of talent that he has dreamed of for years while in Portland. Losing the defensive presence of Jrue Holiday cannot be discounted, but in his place Lillard enters as a big shot taker and maker. Lillard has been a consistent performer in the playoffs throughout his career, averaging 25 points per game on 41% shooting from the field and 37% from three. This alone is a huge improvement offensively from what Holiday was able to contribute.


Many will see this trade from the perspective of Lillard getting his opportunity to shine on the biggest stage alongside the co-star he has needed his entire career. But the perspective of the Bucks may be more important. Acquiring Lillard sends a message to Antetokounmpo and the league as a whole. That message being that this team is committed to competing for titles today, that it will not accept the idea of a small market team resting on its laurels after winning one championship.


The Bucks recognized that they struck NBA gold with Giannis and want him to stay with the franchise as long as possible. Instead of operating along the fringes and bringing in more minimum contract players, the Bucks took a big swing. Could it fail? Absolutely. But it is a move that the Bucks had to make to keep their star player on the roster long term.


Staying Aggressive


In the NFL, teams that have remained aggressive have been rewarded with success. The Rams were aggressive in accumulating talent and it led to a Super Bowl win for instance. The NBA is a league of stars and superstars. If you have one or two superstars you are positioned for success. The Los Angeles Lakers employed this strategy when they acquired Anthony Davis from New Orleans to pair with LeBron James and it ended in a championship for them in 2020. Because the Lakers play in a large media market in Los Angeles, many simply assume that executing these sort of transactions is only for teams in “desirable” locations.


But in the modern NBA landscape, market size is not the be all and end all when it comes to a player's marketability. Russell Westbrook was a marketable superstar for years in Oklahoma City, which is the furthest thing from a large market for instance. What matters is making moves that translate to winning. Basketball culture in the NBA is defined by winning titles, whether we like it or not. Carmelo Anthony, who recently retired after a 19-year career, won just about everything you can in basketball (Olympic gold, college national championship, individual accolades, etc.) but never won an NBA Championship, which will limit how fans view him historically.


With that culture of titles in mind, to keep a star player happy a franchise needs to continue being committed to winning. Roster overhaul needs to always be an option while the star is playing at an elite level. That is what the Milwaukee Bucks have done. While some people may lament that the team got rid of Jrue Holiday just a couple of seasons removed from him helping them win a title. That is smacks of cold business. But the reality is that if the team did not show Giannis that it was dedicated to winning today, then he would have been gone tomorrow. By acquiring Damian Lillard, they are sending a message that they are trying to win right now.


It would have been very easy for the Bucks to simply make moves on the edges, a role player here and a depth piece there. Instead, they roll the dice and go all in with a player that will make big shots in the playoffs. Could it fail spectacularly? There is certainly a chance that it will. But if it works, the reward will be worth every bit of risk. In a landscape of larger contracts and more demanding collective bargaining, these types of moves are to be expected. Teams will continue to be aggressive to avoid trade demands, leading to fascinating paintings like Giannis and Dame. As basketball fans, we are all in for a treat.


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