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Damian Lillard trade: Ranking potential mystery teams in talks with Blazers

Andrew Hanlon
Andrew Hanlon

Rip City Project

Giannis Antetokounmpo, Milwaukee Bucks (left); Damian Lillard, Portland Trail Blazers Mandatory Credit: Benny Sieu-USA TODAY Sports

Finally some good news for the Portland Trail Blazers on the Damian Lillard trade front. ESPN and Andscape’s Marc Spears reported on Sept. 18 there’s an Eastern Conference mystery team that’s held trade talks with Portland surrounding its star point guard. If these latest Blazers rumors are true, things could get real interesting real fast.

Dame’s camp has made it crystal clear for more than two months that the seven-time All-NBA star’s preferred landing spot is with the Miami Heat – and only the Miami Heat. The Blazers, however, aren’t interested in what Miami has to offer – mainly a few future first-round picks, pick swaps and a young player.

Portland has no appetite for the Heat’s best trade chip, guard Tyler Herro, which would mean a third team would need to be involved to get a deal done. Talks are set to ramp up as teams get closer to training camp in the beginning of October, but to this point, nothing concrete has come out of the Heat-Blazers rumors.

The best thing that could happen for Portland is for Miami to get desperate as the season approaches or for another team to get involved in the sweepstakes, either to drive up the price for the Heat or to simply make a more attractive offer the Trail Blazers may accept.

Now, it appears that’s exactly what’s happening – but who might be this unnamed Eastern Conference team that’s part of these latest Blazers rumors?

Ranking 3 potential mystery teams that could be in talks with the Portland Trail Blazers over a Damian Lillard trade

Most likely potential mystery team in trade talks for Lillard: Brooklyn Nets

The Brooklyn Nets have surfaced in rumors surrounding the 33-year-old since he made his trade demand on July 1. There are legitimate reasons why it would make sense for the Nets to bring in someone like Dame, but there are also plenty of reasons why it makes no sense at all.

Brooklyn just got out of the superstar drama business after trading James Harden to the Philadelphia 76ers and Kevin Durant to the Phoenix Suns after both asked for trades of their own. Why would the Nets throw themselves back into that type of mess?

Brooklyn was a pleasant surprise after the KD trade, riding Mikal Bridges and a collection of high-caliber role players to the East’s No. 6 seed. The team is running it back with most of that squad intact.

Adding a superstar such as Lillard to a core of Bridges, Cam Johnson, Nic Claxton and Dorian Finney-Smith (and potentially Ben Simmons) would certainly vault the Nets into the top half of the conference.

Brooklyn wouldn’t have to tear apart its roster to make the Blazers an attractive offer, either – it has seven unprotected first-round picks between 2025 and 2030 and a handful of young players who wouldn’t play a significant role on a contending team. It would head into 2023-24 as a deep squad with a superstar in Lillard and a budding star in Bridges.

On the flip side, after a few years of drama the Nets are finally building for the future, not the immediate present, with that collection of players and assets. Trading some of it for an aging player who’s owed $216 million over the next four seasons would be a major risk.

Could the Toronto Raptors be the mystery team in Damian Lillard trade talks with the Portland Trail Blazers?
Damian Lillard, Portland Trail Blazers (Photo by Cole Burston/Getty Images)

Another potential mystery team in trade talks for Lillard: Toronto Raptors

We’ve seen this movie before. A superstar asks for trade, has a list of teams he wants to go to, the Toronto Raptors ignore that list and take a massive risk on said superstar in hopes of winning a championship, even if he leaves and/or is unhappy.

The first time around, it was Kawhi Leonard, and it worked to perfection as Leonard did indeed lead Toronto to the 2019 NBA Title. Could Raptors President Masai Ujiri come out of nowhere off the top rope, surprise the league with a deal for Lillard and pull it off again?

Toronto doesn’t have as much to offer Portland as Brooklyn does, but its cupboard isn’t bare, either. The Raps owe their 2024 first-rounder to the San Antonio Spurs, but after that they control all their own first-round picks.

Pascal Siakam would likely have to head back to Portland to make the salaries work, which wouldn’t be ideal from a Blazers perspective, but a $37 million expiring contract could be useful for a rebuilding team, and an extra first could sweeten the deal enough to make it more attractive to the Trail Blazers.

The idea for the Raptors would be to add Lillard to the duo of OG Anunoby and Scottie Barnes, both long, switchable defenders who could cover for Dame’s defensive weaknesses. Toronto’s most significant problem last season was a lack of offense and shot creation – that problem would be solved as soon as Lillard crosses the Canadian border.

Ujiri’s done it before; it’s not impossible for him to do it again, especially when considering Kawhi was a one-year rental while Dame is locked into a contract for four more seasons. It’s still risky, but less risky than the Leonard trade.

Could the Bucks be the mystery team to trade for Damian Lillard from the Portland Trail Blazers?
Giannis Antetokounmpo, Milwaukee Bucks; Damian Lillard, Portland Trail Blazers (Photo by Abbie Parr/Getty Images)

Most shocking potential mystery team in trade talks for Lillard: Milwaukee Bucks

Cue the gasp.

If the Milwaukee Bucks are the unnamed team involved in these current Blazers rumors and could actually pull off a Lillard trade, it would change the landscape of the league.

A Dame and Giannis Antetokounmpo duo would be incredible. The Greek Freak could be setting screens to free up one of the greatest shooters of all time. Either player is capable of dominating a game by themselves offensively.

The whole “your turn, my turn” approach would actually work in Milwaukee.

The biggest issue, and the one that makes the Bucks the most unlikely team involved in Spears’ report, is Milwaukee’s lack of assets. A deal would probably be built around Jrue Holiday, a 2029 first-round pick, pick swaps in 2028 and 2030 and young players such as Marjon Beauchamp and Andre Jackson Jr.

That’s not a very attractive package for the Blazers. In fact, it’s less attractive than whatever Heat offer is currently on the table.

But Giannis’ recent comments about potentially leaving the Bucks for a better championship situation could make Milwaukee desperate. Acquiring Lillard may put those talks completely to bed as he and Antetokounmpo could chase titles together for at least the next four years.

Andrew Hanlon

Andrew Hanlon

Andrew is a Site Co-Expert for Pippen Ain't Easy. He earned a degree in Journalism from the University of Wisconsin-Oshkosh and began covering high school sports in 2014. He's covered the NBA since 2021, and his work has been featured on FanSided, SB Nation, Yahoo! Sports, Sportscasting, and GiveMeSport. He’s been in his PAE role since 2024 and previously held the Site Expert position for Rip City Project (Portland Trail Blazers). When he's not writing about, talking about, or watching sports, he can be found playing and coaching them with his five kids.