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The first picture in Damian Lillard’s July 9 Instagram post was a family photo of himself, his wife and three young children. If you continue to swipe through the Portland Trail Blazers star’s post from that day, there were also photos of his agent Aaron Goodwin, Blazers general manager Joe Cronin and finally him practicing his very valuable jump shot. Lillard made the Instagram post after signing a two-year, $122 million extension with the Blazers. If the six-time NBA All-Star completes his contract with Portland through the 2026-27 NBA season, he will have made nearly half a billion dollars. Knowing that his generational wealth could have a long-term impact on his immediate family and close friends, Lillard also thanked the Blazers in the post for “allowing me to take care of generations of my family.”