On Sept. 27, shockwaves were sent across the NBA world when the Portland Trail Blazers traded seven-time all-star and their all-time leading scorer, Damian Lillard, to the Milwaukee Bucks. The Phoenix Suns were also involved in the blockbuster trade.

The final details of the trade include Lillard, Jrue Holiday, DeAndre Ayton, Toumani Camara, a 2029 unprotected first-round pick and unprotected 2028 and 2030 pick swaps with Milwaukee going to Portland. 

Jusuf Nurkić, Nassir Little, Keon Johnson and Grayson Allen are headed to Phoenix.  

Four days after the original trade, the Trail Blazers sent Holiday to the Boston Celtics in exchange for Malcolm Brogdon and Robert Williams III, a 2024 first-round pick via the Golden State Warriors, as well as a 2029 unprotected first-round pick. 

Both of these trades dramatically changed the outlook of the Eastern Conference for the 2023-24 season. Even though the Bucks and Celtics were already championship contenders, their respective trades for Lillard and Holiday have made them the top two favorites. 

According to BetMGM, the Bucks are the favorites at +375, and the Celtics are a close second at +400. The defending NBA champions, Denver Nuggets, are third at +500.

The two teams are also the clear front runners to win the East, with the Bucks at +175 and the Celtics at +200. The next closest team is the Philadelphia 76ers, who come in at +800.

When Lillard first requested a trade on July 1, it seemed like the Miami Heat was the only team he would be willing to play for. On July 28, the assumptions were solidified as the NBA gave a memo to all 30 teams, that Lillard’s trade request was only to be fulfilled by the Heat. 

Even though it seemed like “Dame Time” would be headed to South Beach, the Trail Blazers and Heat never gained traction in trade talks. It was reported that the Blazers wanted either Jimmy Butler or Bam Adebayo, the two best players on the Heat, in exchange for Lillard. 

This is one of many times Miami has missed out on acquiring a superstar talent since 2019, the off-season it acquired Butler. 

Since that off-season, the Heat have missed out on Bradley Beal, Donovan Mitchell, Kyrie Irving and now Lillard. Even though they have missed out on the big fish, the Heat have made the finals twice in the last four seasons. They lost to the Los Angeles Lakers in the 2020 bubble and the Nuggets last season. 

In their run to the finals last season, the Heat beat the Bucks in the first round and then the Celtics in the Eastern Conference Finals. 

The Heat also lost two key depth pieces from that finals run. Max Strus is joining Mitchell on the up-and-coming Cleveland Cavaliers, and Gabe Vincent will be joining the Western Conference finalist, the Lakers. After playing in only one game during the playoffs, Tyler Herro will once again be playing a pivotal role for the Heat if they want to make another deep postseason run with their aging superstar in the 34-year-old Butler. 

After winning the 2021 NBA Finals, the Bucks suffered two early exits from the playoffs, losing  the second round in 2022 against the Celtics and in the first round to the eighth-seeded Heat in 2023.  

For the first time in his career, Lillard won’t be the primary scoring option. In Milwaukee, Lillard will join two-time MVP Giannis Antetokounmpo to form one of the best duos in the league. 

Even though the NBA is a superstar-driven organization, and the Bucks have two of the best players, it is tough to win a championship without having strong depth pieces behind the stars. 

To go along with Lillard and Anteokounmpo, the Bucks have several reliable options. Khris Middleton is a three-time All-Star and has been with the Bucks since the 2013-14 season. Since joining the Bucks in 2018-19, Brook Lopez has re-invented himself to become one of the best shooting big men in the league. 

Behind its four proven contributors, Milwaukee has Malik Beasley, Cameron Payne, Pat Connaughton and Bobby Portis. All of them are solid players who have proven themselves to be a part of a championship-caliber team. 

One of the only question marks for the loaded Bucks will be first-year Head Coach Adrian Griffin. Griffin will be replacing the Bucks’ title-winning coach, Mike Budenholzer, who was fired due to the team’s two recent postseason failures. Griffin has 15 years as an assistant coach, including coaching on the 2018-19 champions Toronto Raptors coaching staff. 

As for the Bucks’ top competition in the East, the Celtics also reloaded their roster this offseason. 

Boston made the NBA Finals in 2022 and lost to the Warriors. This past season, it fell one game short of making back-to-back final appearances after losing to Miami.

Out of the Celtics’ top 13 players who played the most minutes last season, six of them are gone. The most significant losses will be the 2021-22 Defensive Player of the Year Marcus Smart, Grant Williams, Robert Williams III and Brogdon. Both Smart and Williams were on the 2021-22 team. 

Two of the new players will be Holiday and Kristaps Porzings. Holiday is a direct replacement for Smart as the team’s point guard. The move could be an upgrade, as Holiday is a five-time all-defensive team player and is offensively better than Smart. As for Porzingis, he will fill in as either a power forward or center. Even though Porzingis is one of the tallest players in the league standing at 7’3, he is an excellent shooter and is coming off a .385 3pt% season. 

As for Lillard’s former team, the Trail Blazers are looking toward the future as they have several young pieces to build around. Scoot Henderson was the third overall pick in the 2023 draft and is expected to be the face of the franchise in the future. Joining Henderson will be his backcourt partner Anfernee Simons, Jeremi Grant, who has averaged over 20 points per game over the past three seasons, and Ayton, a former first-overall pick. 

The depth behind them could be better but is far from awful with Brogdon, athletic freak Shaedon Shape, defensive savant Matisse Thybulle and shot blocker Williams III. 

Even though the Blazers won’t be making any noise in the playoffs should they make it, they will be an intriguing team going forward. 

While Portland deserves some credit for rebuilding its weak roster with the two trades of Lillard and Holiday, they never should’ve been in this situation to begin with. All of this could’ve been avoided if its front office made the necessary roster moves to build around Lillard and his former all-star backcourt partner CJ McCollum. 

The same argument can be made that they didn’t do enough early in Lillard’s career to solidify the roster with him and former Blazers’ star LaMarcus Aldridge. Even though Lillard, Aldridge and McCollum had two seasons together, McCollum broke out the season after Aldridge left. 

The Blazers had the opportunity to have a solid big three but let Aldridge leave for the San Antonio Spurs during the 2015 free agency. 

While winning a championship then would’ve been difficult regardless due to the Warriors dynasty, the Blazers certainly could’ve done more to be competitive once they made the playoffs. During the Blazers’ seven-year streak of making the playoffs from 2013-14 to 2020-21, they had just a 22-40 record and only made the Western Conference Finals once, where they got swept by the Warriors in 2019. 

Going forward, it appears that the Blazers have a very bright future ahead of them if they make the right moves. As for the Bucks, they are doing something the Blazers should’ve done seven years ago; going all in to help their franchise player maximize his career.