NBA Offseason: Exploring the Top Three Betting Favorites to Land Damian Lillard

After years of speculation, Damian Lillard has officially asked for be traded by the Portland Trailblazers. The 32-year-old point guard has spent his entire 11 season career in Portland, but now he will have a chance to take his considerable talents to a championship-contending team. Bookmakers have already set odds for the favorites to land the star, so now is the time to get your offseason bets in.

Below we will share the top three betting favorites to land Lillard according to DraftKings Sportsbook. We will discuss why each team is chasing Lillard, why he would want to go there, and the issues they may face. If you are looking for some NBA betting this offseason, we have you covered.

The Heat are the heavy favorite to land Lillard this offseason. It has been reported by multiple outlets that is the location he wants, and we have seen him hinting at it on social media over the last few weeks. It is hardly surprising considering the Heat’s recent Finals appearance and long history of success. Lillard has made it clear he wants to compete for a title, and his addition to the Heat would make them one of the favorites to win next year. 

While DraftKings and many league analysts think Miami is the frontrunner, they will need a third team to get this deal done. Portland has made it clear they will want a big return for Lillard, and the Heat don’t have enough. There are some teams that have expressed interest in joining in on a trade, but that still may not be enough. While the Heat are the betting favorite, that is still a major hurdle they will have to overcome.

Boston already made a big splash in the offseason when they traded for Kristaps Porzingis, and now they are being linked to Damian Lillard. The Celtics do still have some assets to trade, one of which could be Jaylen Brown. The Celtics star has had issues with the team, and he has yet to sign the supermax deal Boston has offered him. That could leave the door open for a sign-and-trade, which would give Portland an All-Star in return. 

Jaylen Brown would be better than anything that Miami could offer, but it will depend on how his contract negotiations go. Many league experts are saying Brown’s supermax delay is a major red flag that things may not be fixable between him and the Celtics. While a trade would then make sense, they would need Brown to cooperate, which may not happen. They also need to convince Lillard to come there, something he has not expressed interest in. At +550 Boston is a tempting bet, but it’s hard to bet much on them until we know more about the Jaylen Brown situation.

While Lillard has officially requested a trade, it is a mistake to count Portland out. The star has been loyal to the team for eleven years, despite the teams well-documented struggles. He has pushed them to bring in other stars, showing that he truly wanted a chance to win in Portland. If the Trailblazers aren’t blown away by a trade offer, they could opt to try and trade for another star. The team has some good young talent, and another star to play with Lillard could get them back to the playoffs. While that may not make them an automatic championship contender, the move by the front office could be enough to keep the superstar content.

The biggest issue with this plan is that Portland has tried to get Lillard help in the past but failed. The point guard has tried to help recruit players, but the small market and lack of success makes it a less-than-appealing option. There is also the fact that Lillard has asked for this after years of loyalty. Rejecting that request could be seen as a slap in the face to him, and lead to an ugly situation where the Blazers lose their leverage. Of all these bets, Portland at +700 could be the best combination of value and probability.