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How We Got to This Point

LaMarcus Aldridge’s Departure and the Start of Dame Time

It almost feels hard to believe now, but there was a time when Damian Lillard wasn’t the main guy in Portland. They were LaMarcus Aldridge’s team.

The consistently excellent big man led the team in points per game in each of the three seasons that he played with Lillard. But that’s not to say that Lillard was just along for the ride.

Dame was the missing piece of that team, and the team quickly rose from 28-38 without Dame to 33 wins in year one and 54 wins in year two.

That season, Lillard scored a famous game-winner against Houston to send Portland to their first second-round appearance since 2000.

They entered the 2014-15 season with lofty expectations and started the season on fire, winning 12 of their first 15 games and won 30 of their first 38 games.

At that point, they were neck and neck with the Warriors for the first seed in the west and even had more wins than them, although the Warriors had four games in hand.

They would fall off slightly in their next few games but were still fighting with Memphis for the second seed before Wesley Matthews’ career-altering Achilles tear.

Matthews’ injury changed the roles of many players throughout the roster, as he was their third-best player behind Aldridge and Lillard.

They fell all the way to sixth in the standings but got the fourth seed due to winning the division (old playoff format). They lost to Memphis in five games, and that was the last time that Dame wasn’t “the man” in Portland until 2023.

Aldridge was heavily recruited in the offseason, by teams such as the Lakers, Mavericks, Spurs, and Suns. In the end, he decided to join San Antonio’s proven core. The other starters, like Matthews, Nicolas Batum, and Robin Lopez, also left in the summer.

That made Lillard “the guy,” a fact that was reinforced when he signed a five-year, $120 million contract extension. No one expected the team to win many games in 2015-16.

That included former team owner Paul Allen, who said: “We are now able to pivot from being a playoff team to being a team that’s going through a transition to hopefully being back in the playoffs before too long.”

However, Lillard and the breakout of CJ McCollum helped the team to rally from an 11-20 start to a playoff berth and yet another second-round appearance.

The Disastrous Summer of 2016 and Its Consequences

The summer of 2016 set multiple NBA teams back several years. It was the perfect storm; an unprecedented cap spike to go along with a very underwhelming free agency class (except for Kevin Durant).

The Blazers were one of those teams that spent their money terribly in that offseason.

They spent money to bring in Evan Turner and Festus Ezeli (who never played for the Blazers) and spent even more money to retain Maurice Harkless, Allen Crabbe, and Meyers Leonard.

These moves culminated in the Blazers going 41-41 and getting demolished by the Warriors in the first round. This makes the 2017-18 and 2018-19 seasons even more of a missed opportunity.

In 2017-18, Damian Lillard finally made the All-NBA First Team and led the Blazers to the third seed, which included a 13-game winning streak midway through the year.

After a disappointing playoff exit at the hands of the Pelicans, The Blazers started the next season on fire and won 53 games, the eighth-most in franchise history.

Lillard then proceeded to have an all-time great playoff run, winning against the favored OKC Thunder and Denver Nuggets before losing to the Warriors in the conference finals.

Now that we know that this was the peak of the Lillard era in Portland, it really makes you think what he could have accomplished had the Blazers been smarter with their new-found cap room and saved it for the next two seasons.

They could have signed players like Kyle Lowry, Julius Randle, and Aaron Gordon.

The 2019-20 season was a complete disaster, as the team took a nosedive defensively. Despite Lillard and McCollum’s shortcomings on defense, the rest of the squad was solid on the defensive end.

With the gruesome injury to Jusuf Nurkic, and the departure of Al-Farouq Aminu (who was one of the most underrated defensive players during that era), the team regressed heavily on defense and Damian Lillard had to play “hero ball.”

Dame took more shots and threes than he ever had before just to give his team a fighting chance, which was made apparent by his three 60-point performances that season.

Nurkic returned in the Bubble and the team sneaked into the playoffs but lost to the Lakers in the first round.

The 2021 Playoffs and the Beginning of the End

Many years from now, when people start to reminisce about Lillard’s time with the Trail Blazers, after they retire his jersey, people will point at the 2021 playoffs and the ensuing summer as the beginning of the end of “Dame Time” in Portland.

Right before the start of the 2020-21 campaign, which featured yet another free agency period with no major additions, the first real rumors regarding Dame’s future with Portland began to pop up.

Stephen A. Smith claimed that Lillard “might have grown frustrated by the Blazers’ inability to land major stars.” He added that Dame “would entertain going to the Lakers or the New York Knicks.”

Another season went by with Dame playing “hero ball” and carrying the team to the playoffs, but what happened in the postseason was truly shocking.

Lillard and the Blazers took on the Nuggets, who were missing Jamal Murray after he got hurt late in the season.

This series looked pretty even on paper, but it was an even more egregious version of what happened to Russell Westbrook in the 2017 playoffs against Houston.

Lillard couldn’t sit on the bench, because whenever he did, his team would get slaughtered. He averaged 34.3 points and 10.2 assists while shooting 46.3% from the field and 44.9% from three.

But whenever he left to take a breather (averaged 41.3 minutes per game), his team would get outscored by a wide margin (Lillard averaged a +47.0 Plus/Minus Net per 100 Possessions, which showed that his team only stood a chance when he was on the floor).

This was at its most apparent in Game 5, where Lillard broke the record for most threes in a playoff game with 12 threes and played 52 minutes, but his team just couldn’t keep up in the six minutes that he spent on the bench.

Recently, Lillard revealed that this series “was probably the most frustrated I’ve been in my career.” Dame’s frustration went unnoticed by the Blazers’ front office, as they did next to nothing in the offseason.

The 2021-22 season was a lost year for Lillard and the Blazers but with the rise of Anfernee Simons and the acquisition of Jerami Grant there was a bit of hope for this team last season, but they fizzled out after the All-Star break.

The Blazers declined to trade their 2023 first-round pick, which caused Lillard to demand a trade. With their young core of Simons, Scoot Henderson, and Shaedon Sharpe, they finally pulled the trigger and ended the Lillard era in Portland.

The Future In Milwaukee

Sure, Milwaukee isn’t a big market, and Dame probably had his heart set on Miami, but this trade was probably as good as it would get for all parties involved.

Dame now gets to play with one of the best players in the world, Giannis Antetokounmpo, and he actually has to play second fiddle to another star for the first time since his days with Aldridge.

He’ll be joining a team that has already been to the promised land before, with much of the championship core still intact. They are also hell-bent on revenge.

The last time that the Heat humiliated Giannis and the Bucks in the playoffs, they would get a star guard (Jrue Holiday), sweep the Heat, and win the NBA championship. If you’re a believer that history repeats itself, you should be very scared of the new-look Bucks.

As for the other teams, the Suns managed to add some much-needed depth and they essentially replaced Deandre Ayton with Jusuf Nurkic. Nurkic is more offensively complete than Ayton, but is older and has less upside.

I’m still very skeptical about this Suns team. As for Ayton, he finally gets a chance to prove himself as a number-one overall pick, as he gets to play in a very fun and youthful team that will grow together.

Jrue Holiday probably won’t be a part of this project, as many contending teams have expressed interest in him, but the Blazers won’t let him leave for scraps.

He is a proven winner who is one of the best leaders and defenders in the NBA and just made an All-Star team. He won’t come cheap.