Two weeks ago, the Trail Blazers and Damian Lillard agreed to a $194 million extension that runs through the 2024-2025 season.

While that’s a staggering amount of money, Lillard means far more to this city and organization than any numbers in the win-loss columns or the salary sheet could ever capture. He’s earned every dollar of that contract on the court, carrying overachieving rosters to the playoffs year after year with heroic regular season performances, exceeding every expectation - except his own - to become a perennial MVP candidate.

Perhaps more importantly, he’s shown his true value off the court, embracing the city of Portland in a way that no superstar ever has (or I thought ever would). Between his work with Portland teens through his RESPECT campaign, his commitment level to the franchise, and the example he sets within the organization and community, he represents everything you’d want in a superstar and more. Like I said, I want him to have all the money.

Coming off that incredible run to the Western Conference Finals, though, something has been eating away at my excitement and title hopes for next year. Once again, Lillard didn’t play that well in the playoffs. Now before you rush to the comments to excoriate me, hear me out! (Then excoriate away).

While Lillard’s playoff woes have been well-chronicled after previous postseason flame-outs — especially following the disastrous sweep to New Orleans — this year’s extended run seems to have whitewashed his struggles. The Blazers invested the GDP of a small nation in him, along with their playoffs hopes for the next few seasons. He’s paid like a top-five player, but when the playoffs roll around, he often hasn’t looked the part.

To be clear, Lillard has reached dizzying highs in the postseason. His series against the Thunder was transcendent. Dame may act New Testament off the court, but over those five games, he went straight Old Testament on Russ and Friends — averaging 33 points with 5+ threes and shooting splits above 45%. In the series-clinching game, Dame bore witness to Westbrook’s taunts and blasphemies before calmly pulling down the temple walls of the Moda Center on his head with 50 points and a 37-foot lightning strike at the buzzer. Then he waved goodbye and salted the earth behind him, effectively ending that version of the Thunder. They traded away Paul George and Westbrook a month later. Oklahoma City worshipped false idols and fake triple doubles, so Damian cast their entire franchise into the rebuilding flames.

The Shot & The Wave: Blazers’ Damian Lillard waves the Thunder out of the Moda Center after deep game-winner pic.twitter.com/OBFvgDCgo2 — Ben Golliver (@BenGolliver) April 24, 2019

He also played an incredible series in his playoff debut against the Houston Rockets, averaging 25.5 points and 6.7 assists per game, all while shooting 46.4% from the field and almost 50% from three. Oh, and he knocked down yet another series-ending three. This one effectively ended the playing careers of Dwight Howard and Chandler Parsons, as well as the coaching career of Kevin McHale. When Dame gets hot in a series, opposing franchises get torn down.

Outside of those two series, though, his struggles have defined his resume more than his triumphs. Let’s take a closer look.

The Numbers

From a pure numbers perspective, Damian was low-key bad against the Nuggets and Warriors this year. He still managed to put up impressive raw counting stats, but his efficiency plummeted. Over those 11 games, he shot 39.5% from the field and 31.7% from three. Portland needed Steph Curry Lite, not Diet DeMar DeRozan.

Perhaps most surprising, Lillard also coughed up the ball at an alarming rate, especially against the Warriors. Usually one of the steadiest hands in the league, Lillard committed almost 5 turnovers a game, many of them careless and unforced. Bad passes like this killer at the end of the first half of Game 4 are errors we’re just not used to seeing from the All-NBA point guard. Some of these struggles can be attributed to the absence of Nurkic, Dame’s main release valve in the short roll, or the separated rib he suffered in Game 2, but many resulted from sloppy passing and ill-advised drives.

For his career, Lillard’s playoff stats hew reasonably close to his regular season production, suffering a slight-but-expected dip in total production and shooting percentages. If we exclude the two outlier series in which Lillard dominated, however, and instead isolate and focus on the other eight, his numbers look much worse, especially his efficiency. He shoots 4% worse from the field and 7% worse from the three in the playoffs - two big dips for a player who puts up volume and at his best isn’t painting shot charts green.

Even more troubling, Dame seems to be trending downward. He’s reached a new level during the last two regular seasons, garnering First and Second Team All-NBA selections. Out of the four playoff series that followed, though, three have been his worst as a pro.

We already covered the Nuggets and Warriors series, but the New Orleans sweep ranks as his most unsightly. He scored 18.5 points a game, shot 36% from the field, and barely managed an even assist-to-turnover ratio. His exorcism of the Thunder made it seem like those struggles were in the past. After they reared up again in the next two series, it’s fair to ask which series represents the aberration — his terrible one against the Pelicans, or his amazing one against the Thunder?

Either way, looking at the numbers makes one thing clear. Lillard’s ability to deliver night-in and night-out during the regular season has not translated to the playoffs. Part of this inconsistency is a natural tradeoff for having a superstar at the point guard position. He lacks the physical tools to impose his will on a game through brute force like LeBron or Kawhi. Good competition can knock him off his game, and as we’ll explore, Damian has faced some of the stiffest.

The Competition

As always, statistics require context, and boy does the context matter for Damian. Basketball isn’t played in a vacuum, especially when you’re responsible for generating the bulk of your team’s offense. The competition and opposing defense need to be accounted for.

In order, here are the point guards he’sfaced in the playoffs, as well as the result for Dame:

Talk about a murderers row. Even amidst the current point guard boom, Dame has played a disproportionately tough run of floor generals. The easiest matchup was... *squints*...Patrick Beverley? In Dame’s playoff debut? Oh my.

For comparison, here are the point guards Curry faced during the Warriors first title run in 2014-2015:

Norris Cole

Mike Conley Jr.

37-year old Jason Terry

Matthew Dellavedova

Not quite the bevy of hall of famers that Dame’s dealt with. Basketball can’t be broken down into individual matchups, though. It’s a team sport, and the best teams utilize all five players to execute their defensive schemes and corral the opposing team’s best player. Unfortunately for our guy, Dame has also faced some of the best five-man squads ever assembled.

Here’s every teams that has knocked him out of the playoffs.

2014 Spurs : Came within 5 seconds of winning the NBA Finals. The same roster went on to dominate Lebron and The Heat and win the Finals the following year. An all-time team filled with Hall of Fame players.

: Came within 5 seconds of winning the NBA Finals. The same roster went on to dominate Lebron and The Heat and win the Finals the following year. An all-time team filled with Hall of Fame players. 2015 Grizzlies : The height of grit-and-grind with Mike Conley Jr., Marc Gasol, and Tony Allen. And the Blazers were still reeling from the loss of Wesley Matthews.

The height of grit-and-grind with Mike Conley Jr., Marc Gasol, and Tony Allen. And the Blazers were still reeling from the loss of Wesley Matthews. 2016 Warriors: Set the NBA record for wins in a season and were a historic collapse away from winning the NBA Finals.

Set the NBA record for wins in a season and were a historic collapse away from winning the NBA Finals. 2017 Warriors: Same team that won 73 games, minus Harrison Barnes but plus Kevin Durant. They went 16-1 in the playoffs and won the NBA finals.

Same team that won 73 games, minus Harrison Barnes but plus Kevin Durant. They went 16-1 in the playoffs and won the NBA finals. 2018 Pelicans: Not a great team by any means, but with Holiday and Anthony Davis, they had the perfect 1-5 combo to stymy Lillard’s pick and roll.

Not a great team by any means, but with Holiday and Anthony Davis, they had the perfect 1-5 combo to stymy Lillard’s pick and roll. 2019 Warriors: Still the Warriors, albeit missing Kevin Durant. But the Blazers were missing Nurkic, so...wash?

That’s crazy. Outside of the Grizzlies and Pelicans, Lillard has only lost to historically-great teams. Of those two, just the Pelicans really stand out as a series that people expected Portland to win. Dame has the misfortune of routinely bumping up against the best teams in the league, and the best teams have understood how to gameplan for him.

The Defensive Schemes

Opposing teams know that Lillard’s mastery of the pick and roll powers everything the Blazers want to do on offense. The lengths they go to neutralize him are, quite frankly, ludicrous. Outside of Nick Nurse and the Raptors throwing a box-and-one at Curry to end Game 2 of the Finals, I’ve never seen NBA coaches sell out to contain one player like they do Lillard.

The book on Damian for years has been to trap him on every pick and force him to give the ball up. Make someone other than him or CJ beat you. So this year he adjusted and started aggressively attacking the double to get splits going downhill. This largely worked against the Nuggets inexperienced guards and the perpetually-stuck-in-mud Nikola Jokic. The Warriors are a different monster, though.

Look at this nonsense. First, Lillard has to navigate the Kevon Looney and Klay Thompson hard double coming off the Meyers Leonard screen. If he manages to split it, which often led to turnovers against lanky Golden State defenders, Draymond Green - the last person you’d want waiting for you at the rim - is waiting for him at the rim.

Look at Draymond. He’s focusing all his attention on Dame and the pick and roll, completely ignoring Mo Harkless standing behind in the dunker spot. The Warriors gave Al-Farouq Aminu the same treatment, happy to let him load up his trebuchet and cast rocks from deep. On any given pick and roll, the Warriors devoted three defenders to stopping Lillard. The Pelicans employed a similar strategy, blitzing the high pick with Holiday and Mirotic, trusting Anthony Davis to block off the paint. I’m not sure what any player is supposed to do against that.

For this strategy to work — and it works — you need an all-world defender like Green to guard multiple points of attack, someone with the length to protect the rim, the agility to close out and stay in front of Leonard, and the defensive instincts to read Damian and either contest the layup or recover to Harkless. Very few players in the league can pull off this defensive ballet. In fact, there might only be three: Green, Anthony Davis, and Giannis Antetokounmpo. Lillard’s just had the misfortune to play two of them year after year in the playoffs (I would consider it very good fortune if he plays a series against the third)

In the play above, Dame made the right decision and passed the ball to a popping Meyers, who took advantage of no one guarding him and scored 25 points in the first half. The crowd chanted MVP for him! Any defensive scheme that allows something so zany to happen must rely on extreme tactics. In this case, and in the case of every recent playoff series, that means loading up the entire defense to stop Dame, and living with the risk that Meyers goes nuclear.

After facing these defenses for three straight years, Neil Olshey overhauled the roster over the summer to combat it. This meant jettisoning players like Harkless and Aminu who smart defenses could ignore, and replacing them with better playmakers and shooters in Kent Bazemore and Rodney Hood. While we’ll have to see how the new additions shake out, the hope is they can alleviate some of the pressure on Lillard and force opposing teams into more traditional defensive gameplans. Add in the possibility of a big midseason trade, and Lillard might finally have the necessary players around him to unlock his full postseason potential.

If he stays on the roster until the playoffs, Hassan Whiteside could prove an interesting addition to Lillard’s pick-and-roll tool box as a rim-running big who finishes lobs. Prior to Whiteside, the best lob threat Lillard has played with was...Mason Plumlee? While I would never slander a fellow Plumlee, opposing teams didn’t exactly fear his alley oops (unless they were reverse dunks).

Looking Forward

This next playoff run the Blazers make will become the true litmus test for whether Lillard can raise his game in the postseason crucible. The Warriors no longer loom over the league like a sweet-shooting boogeyman, and no other team stepped into their role as the hands-down favorite. Olshey also made the necessary roster changes around Damian to put him in a better position to succeed. Now it’s on the letter O to deliver.

With Lillard, drawing broad conclusions about his ability as a postseason performer can be tricky. He’s already hit two of the most iconic playoff shots in NBA history. He’s logged two of the best series ever for a Blazer. But he’s also disappeared in several others, gobbled up and swept aside by better teams with world-class defenders intent on containing him at all costs.

As news broke of his supermax extension, I kept coming back to one question. Is Damian Lillard good enough to be the best player for four-straight playoff series and win a championship? The answer gets murkier the more I look at it.

The 2020 NBA Playoffs should provide clarity.