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This Rip City reunion may very well end on Monday night, with the San Antonio Spurs up 3-0 in the Western Conference Semifinals and looking so very capable of finishing off Portland's beloved Trail Blazers on their home floor.

And still, Damian Lillard – not to mention the shoe company that recently gave him a blockbuster deal that caught so many by surprise – will have won.

DAGGER: Lillard K.O.s Rockets at buzzer

THE DEAL: Lillard signs huge shoe deal with Adidas

When it comes to the business of basketball and one man's brand, no one has won in these playoffs quite like the Blazers' second-year point guard whose Adidas deal is believed to be the third largest in the entire NBA. The contract – which his agent, Aaron Goodwin of Goodwin Sports Management, told USA TODAY Sports could be "well over $100 million" with very-reachable incentives and is expected to eventually include a signature shoe and apparel – was seen by some as a head-spinner when it was first revealed on April 14.

Lillard was a rising star, to be sure, having won Rookie of the Year in 2012-13 and earned his first All-Star berth in his second season. But he had only received the 22nd most fan votes in the All-Star affair that is widely deemed a popularity contest, and two months later Adidas was making this monumental investment that would put Lillard above the Kobe Bryants and Dwight Howards of the basketball world in terms of shoe deals.

Then came the shot that fit so snug into Adidas' preferred script, Lillard's game-winning dagger from three feet behind the three-point line that not only buried the Houston Rockets in Game 6 of the first round but remains the most memorable moment of this postseason. It was instant bedlam in the Moda Center building, with these loyal fans whose team hadn't reached the second round of the playoffs for 14 years going wild and Lillard spiking his approval rating yet again even after the shot by grabbing the courtside microphone and yelling, "Rip City!" as he let everyone in on his moment.

Such is the power of the playoffs, that memorable time of year when the mainstream audience tunes in and players' images are so often buoyed or broken.

"That's great for his profile and great for his career in terms of his legacy" said David Carter, the USC Sports Business Institute Executive Director and renowned sports marketing expert. "But those can be not only fleeting moments, but easily replaced by other stars in future series. Ultimately, (a player's brand) is still going to boil down to what it has always been: how well does he handle himself on and off the court? How well do the Trailblazers do long-term, and what's his role in the overall team success? After the success, your popularity is much more stable and you can resonate."

The shoe contract can sometimes be a bigger part of a player's business portfolio than his contract with the team he plays for, making the motives and mechanisms involved in these sorts of decisions as relevant to them as the selection of a new coach or a general manager. That is certainly the case for now with Lillard, who will be paid a combined $13.9 million over four seasons on his rookie contract by the time it expires in the summer of 2016. His Adidas deal has an eight-year base, but can be extended from there depending on incentives.

So why did Adidas do this deal, one in which they outbid Nike and may have raised the stakes on future negotiations with one of their other top clients, Washington Wizards point guard John Wall? And beyond Lillard, what is the thought process for these shoe companies when it comes to deciding which athletes will sell enough product to make the investment pay off?

Lawrence Norman, who was vice president of Adidas Global Basketball at the time of the deal but was recently named managing director of Adidas South East Europe, explained in great detail in a recent interview with USA TODAY Sports.

The key decision-making factors in a shoe contract, according to Norman, range from the player's market to his character, personality and style as well as the position he plays. In Lillard's case, he just so happens to be based in the city where both Adidas and their No. 1 rival, Nike, call home. And with Adidas' top basketball athletes, the Chicago Bulls' Derrick Rose (two season-ending knee injuries) and the Houston Rockets' Dwight Howard (negative publicity relating to his Aug. 2012 exodus from Orlando), having fallen on such hard times in recent years, Adidas' competitors in the industry understood that the time was right for them to take a calculated risk on Lillard.

As Norman detailed, the fact that Lillard was not only a point guard but a score-first point guard (like Rose) means he's much more likely to get facetime on camera while playing his way onto the nightly highlight reels that are key for exposure. Winning is key as well, and the Lillard-led Blazers checked that box by going from 33-49 in the regular season a year ago to 54-28 in 2013-14.

Lillard's personality also played a part ("He's very team-first," Norman said), as did his social media following and habits that are among the most unique of any player in the league ("he went from 79,000 followers on Facebook a year ago to 1.3 million; he's got over 400,000 Instagram followers; he's got over 400,000 Twitter followers," Norman said). Everything factored in, Norman said, even good, old-fashioned looks, personal style and the fact that Lillard is interested in sneaker culture.

Norman, who noticed Lillard's habit of pointing to the front of his jersey (the team name) rather than the back (his name) back when he was a relative unknown player at Weber State, said the deal was only seen as a risk because the rest of the world is just starting to see all the sellable sides of Lillard that they have seen since signing him as a rookie two summers ago.

"He's located here, down the street, and he's in our office a lot hanging out with guys from our brand all the time," Norman said. "We know what Damian Lillard is about. We know the value that he puts on family and friendship and the relationship we have. It was not risky at all, knowing that we had the right character, integrity and personality. There was no risk.

"In regards to a long-term deal with a player, there's always risk involved, but with him that risk was minimal because he has such an incredible trajectory. Very few players are Rookie of the Year and then All-Star in their second year, that's rarely seen. So with that in mind, the risk was minimal."

Goodwin is the first to admit that Lillard's game-winner against Houston couldn't have come at a better time. When the shot fell, Goodwin and his business partner/twin brother, Eric Goodwin, celebrated inside the Moda Center along with the rest of the sellout crowd.

But there was a context to this chaos that was lost on all the non-sneaker heads in the building. Lillard's shot not only made this a more profitable playoffs for him and his team, it ended the season of the one Adidas athlete who so badly needed a deep postseason run to continue rehabilitating his battered brand - Howard. In all, there were four other Adidas athletes on the Rockets who were devastated by Lillard's big shot: Jeremy Lin, Patrick Beverley, Omri Casspi and Donatas Motiejunas.

"To see the reaction was crazy," Goodwin said. "(Blazers owner) Paul Allen is normally (calm), but he's jumping. (Blazers general manager) Neil Olshey is jumping. Jim Gatto from Adidas is running around jumping as if Damian is the only Adidas athlete on the court. I realized the importance of that shot, and it kind of brought things into perspective that, 'This kid is special.'"

Goodwin, who cut huge deals for Howard, Kevin Durant and LeBron James when he represented them and who is widely known as the industry leader on this front, heard the whispers in recent weeks when people within the shoe industry and the media questioned the veracity of reports indicating the size of the deal.

"I can say that I understand people who question the deal – most of them haven't done deals of this magnitude so they don't understand it," he said. "But at the end of the day the deal could be well over $100 million, and I don't have any problem saying that and Adidas wouldn't doubt that. Is it $100 million guaranteed? No, it's not. Is there an easy opportunity for that to happen? Absolutely."

"Is (the deal) a game-changer? Nah, I don't think it's game-changer…Will players ask for more now? I'm sure that's going on with Adidas, Nike, the other companies, right now. Will they get them? I completely doubt it."

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