Portland Trail Blazers superstar Damian Lillard has taken the first step toward ending his partnership with the organization. Damian requested a trade from the organization on July 1st after the team could not improve the roster to give him a better opportunity to win a title.

Damian’s trade request comes with a caveat: he only wants to play for the Miami Heat next season. Damian Lillard’s request has created the narrative around the league that Portland must trade him to the Heat out of gratitude for his years of service to the city and organization.

Showing Gratitude to Damian Lillard will result in a bad outcome for the Portland Trail Blazers

Vincent Goodwill of Yahoo Sports stated on July 1st that the Trail Blazers should trade Damian Lillard to his preferred destination because he was a model citizen and the best player in franchise history:

They knew Lillard appreciated how important he was to the Portland community, how he gave the Blazers credibility among the sponsors and corporate folks we don’t think of in these cases.

But it wasn’t going to be enough to keep him forever, and now they’re faced with sending him where he wants to go — an emotional no-trade clause, in a sense, similar to Garnett in 2007. It would be bad form to send Lillard anywhere he doesn’t want to go just because it’s the “best deal” — preserving a long-term relationship with arguably the franchise’s best player (apologies to Clyde Drexler and Bill Walton) should Trump haggle over a particular draft pick or two.

Unfortunately, Goodwill’s suggestion to do right by a franchise player in the back end or past their prime has routinely caused organizational setbacks. For example, Dallas Mavericks owner Mark Cuban said in 2016 that he would acquiesce to every demand from 36-year-old Dirk Nowitzki because of what he has done for the city and franchise.

One of Nowitzki’s requests to the organization was to upgrade the roster to compete for a playoff spot. Dallas acquired Andrew Bogut, Harrison Barnes, and Deron Williams that off-season to make a playoff push. Unfortunately, Bogut and Williams dealt with numerous lower body injuries causing them to miss at least 50% of the team’s games. Consequently, the Mavericks finished 11th in the West with 33 wins.

Nowitzki’s desire to compete for a playoff spot contributed to the team not having better lottery odds to select one of the following players, Jayson Tatum, De’Aaron Fox, or Lonzo Ball, in the NBA Draft as Dallas received the ninth pick. Organizations put themselves in better positions for long-term success when removing gratitude from the equation.

For example, the former president of basketball operations for the Boston Celtics, Danny Ainge, sent Kevin Garnett and Paul Pierce to Brooklyn in 2013 for three first-round picks and a pick swap. Paul Pierce revealed in 2019 that Danny Ainge had a conversation with both players before the trade, informing them that they could be sent to another team due to their age.

The trade was a massive success for Boston as those picks became James Young, Jaylen Brown, Jayson Tatum and Colin Sexton (who was traded to Cleveland for Kyrie Irving). Boston is still reaping the benefits from the Nets trade, as Jaylen Brown and Jayson Tatum are the franchise cornerstones for the team’s current version.

Consequently, the Portland Trail Blazers should trade Damian Lillard for the best package available, as it’ll put the organization in a better position for long-term success.

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