Damian Lillard trade is bound to pay off huge for Blazers as Bucks unravel

Last year was too early to say that the Bucks' decision to go all-in with a Damian Lillard and Giannis Antetokounmpo pairing backfired. Dame had a relatively down year by his standards as the two were figuring out how to play off each other best. They still finished third in the Eastern Conference with a respectable 49-33 record but suffered a first-round playoff exit to the Indiana Pacers as they had to play without Giannis.

But this time around, the Bucks don't look any better. They have an aging roster with Brook Lopez (36), Lillard (34), and Khris Middleton (33). Middleton, unfortunately, has become injury-prone, playing just a total of 88 games in the past two seasons. And as good as the Bucks' starting lineup is on paper, they have significant depth issues.

They also face a similar issue that the Blazers had in their Lillard era—trouble defending guards. ESPN's Tim Bontemps highlights that as a key factor (subscription required) in the Bucks' concerning 1-4 start to the 2024-25 season. Bontemps reiterates what an opposing executive told ESPN: "Watching them, it's just clear these quick guards are able to get where they want."

It sounds like the Bucks could use a lockdown defender. Maybe Jrue Holiday is available?

Revisiting the Damian Lillard trade

Of course, the Blazers proceeded to flip Holiday to the Celtics, who played a key role in helping them get over the hump and win their 18th championship. But arguably, the two most important pieces the Blazers received in either trade were Toumani Camara, who has legitimate All-Defensive Team potential, and the Bucks' picks. Here was the original Lillard deal:

Bucks receive:

• Damian Lillard (via Portland)

Trail Blazers receive:

• Deandre Ayton (via Phoenix)
• Toumani Camara (via Phoenix)
• Jrue Holiday (via Milwaukee)
• 2029 1st-round pick (via Milwaukee)
• Two first-round pick swaps (Milwaukee, 2028 and 2030)

Suns receive: 

• Grayson Allen (via Milwaukee)
• Keon Johnson (via Portland)
• Nassir Little (via Portland)
• Jusuf Nurkic (via Portland)

Portland may have struck gold with Milwaukee's future picks

Over the offseason, CBS Sports' Sam Quinn ranked all 68 traded future NBA first-round picks. Here's where Quinn had the three picks (two of which are swaps) that Portland acquired from Milwaukee:

• No. 9: Milwaukee Bucks, 2028 (swap)

• No. 7: Milwaukee Bucks, 2030 (swap)

• No. 1: Milwaukee Bucks, 2029

The Bucks' 2027 pick, which is owed to the New Orleans Pelicans, is also ranked No. 4 by Quinn. He seemed to have Milwaukee's picks valued higher than the consensus, but that is looking more accurate with each passing day.

When teams aggressively go all in with a blockbuster move and sacrifice a large part of their future in the process, they better be positive that they at least have a reasonable chance of winning it all. Now, with the Bucks' championship chances looking slimmer and their future looking bleaker, trade chatter surrounding Giannis has picked up.

Bleacher Report's Jake Fischer said, "Giannis and Jimmy Butler are the two names—with Butler not coming to an extension in Miami and the Bucks off to a pretty poor start in Milwaukee—that rival executives are looking at."

It would take quite the haul to land a two-time MVP, eight-time All-Star, and Finals MVP who is still in his prime. Regardless, the situation in Milwaukee is on a downhill spiral, and the Blazers are well-positioned to be the main beneficiaries.