The end of the 1967 movie “The Graduate” isn’t quite as famous as its poster, but it remains a classic cinematic moment. Sixty-year-old spoiler: Dustin Hoffman sprints into a church and convinces his crush to run out of her wedding and leap onto a bus with him. But as they drive away, the adrenaline rush and giddiness slowly evaporate. Their blank, uncertain faces linger on screen for an uncomfortable amount of time.
Fin.
At what cost comes happiness?
Every year, there’s a new study trying to pinpoint some income level at which people would be “happy.” Hint: it’s always more than they’re currently making. Even in the eight- and nine-digit world of professional athlete salaries, more is better — a sign of respect, a matter of principle, if nothing else.
For sports teams, however, more money doesn’t always equal better. Leaving aside the dreadful snowballing of the repeater luxury tax, the punitive restrictions of the first and second aprons create legitimate teambuilding quandaries. The more you spend, the harder it becomes to spend — or trade, or sign players, or draft rookies. Phoenix Suns fans can’t get Biggie out of their heads.
The funny thing about the NBA is that teams aren’t even all playing the same game, much less optimizing utility on the same axes. For some teams, yes, chasing championships is the sole goal. Others want to maximize profit. Some want to maintain cultural relevancy, to be part of the local fabric. Money is helpful for all of that, although it’s not the only route.
Nearly every team has some unique mix of goals and resources available to achieve them. Which brings me to a question: When does the pursuit of happiness become self-defeating?
News broke last night that Damian Lillard, still in very early rehab stages from a torn Achilles suffered almost immediately after returning from deep vein thrombosis, would be returning to his beloved Portland on a three-year, $42 million contract. The third year is a player option. A no-trade clause is included.
There are, as always, multiple sides to this. From a basketball perspective, let’s not mince words: It’s horrific.
Lillard was a deserving All-Star last season. He also was one of the league’s worst perimeter defenders and turned 35 three days ago ($42 million is a hell of a birthday present!). Here’s the list of high-level NBA players who have suffered Achilles injuries and returned to anything remotely close to real All-Star form:
Dominique Wilkins
Kevin Durant
That’s it. The Achilles is the most damaging injury an NBA player can have. For a player whose on-court excellence was already feeling a little brittle, to suffer this injury at this time is devastating.
We all hope that he comes back and returns to All-Star level form (and Lillard was one of my favorite players of the 2010s, so few wish for that as fervently as I), but the most realistic outcome is that Lillard’s time as an impactful player is over. Best case scenario, he still isn’t playing for all of next season for a team with playoff aspirations.
This decision comes on the heels of adding Jrue Holiday (who, ironically enough, was the guy the Blazers traded Lillard for two years ago before flipping him to the Celtics and lighting the East on fire; now, they’ve got both their men), who stands to make over $100 million in the coming three seasons himself. While Holiday can still contribute, he noticeably slipped last season and is sledding down the back end of his career, too.
Put another way, the Blazers will pay 30% of the salary cap next season for one ambulatory player and two mentors. Frankly, that feels irresponsible.
The Blazers are not in dire financial straits at the moment, but this will impact their flexibility going forward, particularly as they start negotiating contract extensions with Shaedon Sharpe (a fascinating extension candidate) and Scoot Henderson. Playing free agency will require moving some players around. Portland will need a lot of clarity on their backcourt by the end of next season to feel good about their path forward (and I’m not sure what they do if that realization is, “These guys aren’t enough”).
Racking my analyst hat and putting on my “Blazers #1” foam finger, I see the appeal here. Lillard is a beloved figure in Portland. Fans I’ve interacted with are generally over the moon to have their hero back. Lillard was a legitimate locker room leader and workout warrior during his first Portland tenure, and he and Holiday will provide excellent guidance to the Blazers’ many young ballhandlers over the next few years. Sharpe and Henderson, in particular, are talented players who nonetheless need all the help they can get. The Trail Blazers think Lillard’s return is worth nearly any cost for the vibes alone.
For Lillard, this deal must have him screaming Hallelujahs. Although professional, he reportedly was never happy in Milwaukee, and he pined (fir’d?) to return to his Pacific Northwest family and friends. Now, he’s getting paid to rehab and will have access to the facilities and doctors he’s comfortable with while picking his kids up from school. It is a storybook ending for him (and I have to imagine this will be his basketball ending in some form or another). He put truth to his words to Portland fans after his 2023 trade request was granted: “This isn’t a goodbye, it’s a see you later.” Lillard tried to chase his happiness by asking for a trade to a contender two years ago; he’s since seen the error of his ways.
No, Portland isn’t likely to win a championship anytime soon, but they are building a fun, defense-first organization. I really like a lot of the guys on this roster, even if I’m somewhat confused by how they all fit together. Lillard can be a part of building the next generation of Trail Blazer stars, and who knows? Maybe he can contribute meaningfully in 2027, providing offensive punch to a top-10 defense to help the Blazers make some playoff noise.
Lillard is happy. The fans are happy. The ownership (looking to sell the franchise, don’t forget) is happy. So why amn’t I?
Perfect analogy.
🎵 And here’s to you, Big Dog Robinson 🎵
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