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  • Writer's pictureEthan Hill

“Dollas” and Bucks in Milwaukee

The Milwaukee Bucks Re-establish Championship Aspirations by Trading for Damian Lillard

By: Ethan Hill

October 24, 2023


Photo Credit: Associated Press

After a summer full of rumors, the Portland Trail Blazers finally found a landing spot for their franchise superstar, Damian Lillard. With Portland unimpressed by the package of assets offered by Lillard’s desired landing spot, the Miami Heat, the Milwaukee Bucks swooped in to make a deal happen. By acquiring Lillard, the Bucks now possess one of the most talented rosters in NBA history. Last year, the top-seeded Bucks suffered a humiliating first round exit to the Miami Heat in five games, which led to the firing of longtime head coach Mike Budenholzer and concerns mounting over whether Giannis Antetokounmpo would sign a contract extension to stay in Milwaukee for many years to come. Trading for Lillard this offseason has extinguished the uncertainty brewing within the organization and the fanbase.


From an on-court performance standpoint, the trade is fairly even. The Bucks traded away Jrue Holiday, an above average scorer and an elite perimeter defender, for Damian Lillard, one of the best offensive players and least impactful perimeter defenders in the entire league. The Bucks also gave up a key role player (Grayson Allen) and multiple draft picks to sweeten the deal.


From a business perspective, the Bucks will reap immense financial benefits from this trade, particularly in the short term. They’ve managed to pair one of the most established stars in the NBA (Lillard) with their franchise cornerstone (Antetokounmpo). Milwaukee’s new duo of world-famous superstars will undoubtedly result in an expanded fanbase, more media coverage, more nationally televised games, and a spike in merchandise sales for the team. In fact, the Bucks have already capitalized on their acquisition of Lillard by hosting a “Damian Lillard Welcome Rally” for their fans just three days after the trade was announced. At this rally, the Bucks sold a variety of merchandise, including a limited number of brand new Bucks jerseys emblazoned with Lillard’s name and his signature number 0. To nobody’s surprise, those jerseys were the best-selling product of the event.


Unfortunately for the Bucks, these short-term financial advantages do not mitigate the long-term concerns of the deal. It’s worth noting that Lillard is already 33 years old and is therefore most likely nearing the end of his prime as a player. In fact, in the past two seasons alone, Lillard has suffered frequent injuries which have greatly limited the number of games he played in Portland. If these injuries continue to persist, Lillard could miss crucial stretches of the Bucks season. This could not only put the team’s on-court success in jeopardy, but it could also damage the marketability of their games. Furthermore, he currently has just one year left on his contract, with a player option for an additional year of playing with the Bucks to be accepted or declined by Lillard at the end of this coming season. It is difficult to gauge his commitment to the prospect of playing multiple seasons in Milwaukee. A poor performance from the Bucks this season could lead to Lillard declining his player option and signing with another contender in a larger market, such as the Miami Heat. Lillard has also publicly stated that he’d like to retire with the Portland Trail Blazers, the team which the grand majority of NBA fans will always associate with him regardless of how he performs with the Bucks. This statement makes it seem extremely unlikely that Lillard will commit to playing the remainder of his career in Milwaukee.


The Lillard trade represents an “all in” push from the Milwaukee Bucks. The success of the team this coming season is of paramount importance to the present and future of the organization. Only time will tell how this monumental shakeup of the NBA landscape will pan out for the parties involved.

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