“You know how I think of him? Like a ball of clay. You can mold him however you want.”

“I don’t see it. Can’t shoot. Throws the ball all over the place. Just doesn’t really know how to play.”

Our front office — executives, scouts, video coordinators, analysts — were sitting around the long table in the conference room at the Trail Blazers’ practice facility. The draft was a few weeks away, and we were once again discussing our thoughts on the prospects as a group. We’d go around the room, with each person giving their view, and then collectively deciding how to adjust the player’s current ranking on our board.

“I see why he’s interesting. But I think he’s missing that surge. He’s a rim attacker without a burst off the ground. Just kind of throws himself at the defender. If he plays that way he needs to be able to at least finish well.”

Neil Olshey, our GM, swiveled in his chair and turned to me.

“What do you think, Ben?”

I took a deep breath. Archie Goodwin was a player I thought could be the steal of the draft. This was my chance to make the case — but it wasn’t going to be easy. The room clearly was down on him, and he’d be just another name on the board if I didn’t make a compelling argument. Our first round pick was sitting at #10, and we had picks 38, 39 and 45 in the second round. Goodwin’s range was likely in between those two spots. We’d have to make a trade to get him, and I knew from experience that only tended to happen for players the group was really sold on.

“So I think he’s the kind of player we should really try to get,” I began. “He’s incredibly young, he got to the foul line at a really high rate, and he passed it pretty well. If you look at the list of perimeter players who played like him at his age, it’s a really good list.”

I looked around the room. They were listening, but skeptical.

“I think he’s the kind of player teams should want to gamble on. A lot of players who have performed well above their draft slot in recent history were players like Goodwin: young, with obvious problems but some good statistical indicators. Jrue Holiday, Kyle Lowry, Rajon Rondo…and hitting on a pick like that is the kind of boost our team needs. If he blossoms, he could be the player that takes us over the edge in a few years, the difference between getting knocked out in the first round and consistently making it to the second round.”

I kept going, gaining steam and laying out my argument. When I was done there was a pause, an acknowledgment, and we moved on. I let out a small sigh. I could tell I hadn’t moved the group much. I was fortunate to work with a very open-minded front office in Portland, but, as everyone is, they were anchored to their personal evaluations. My argument may have made them reconsider things a little, but it didn’t move the needle significantly.

I was frustrated, but as the draft approached, I didn’t give up. Whether in group meetings or individually, I kept pressing.

“Here’s a list of players that hit the same benchmarks as Goodwin did at that age. Look how many high level players are on the list!”

“Goodwin is one of the youngest players drafted out of college in history! He has a lot of room to grow!”

“It’s a risk, but how else are we getting a player like that?”

Slowly but surely, I nudged the group. They started to consider it a little more, talking about seeing if there was a way to move into the bottom of the first round if Goodwin was available there.

But the harder I pushed the more uneasy I felt. Clearly Goodwin was far from a sure thing, and yet as I listened to myself I realized that I was selling him like one. I was staking a lot of my reputation on a player that, at best, was a 50/50 bet.

There’s a great scene from Zero Dark Thirty, a movie about the hunt for Osama bin Laden, that I think of every year around draft time. Maya, an intelligence analyst who has unearthed evidence pointing to the compound where bin Laden is hiding, is in a meeting with the CIA Director and other analysts. They are trying to decide whether to take action against whoever is in the house. An attack on that location without taking out Osama would create an international incident, so the stakes are high. They go around the table stating their estimates of the chance the person in the compound actually is bin Laden. Most think it’s somewhere around 60%. And then they get to Maya.

“100% he’s there,” she says, with a defiant jut of the jaw. “OK, 95%, ’cause I know certainty freaks you guys out, but it’s 100.”

Maya’s certitude changes the CIA Director’s opinion. The movie even suggests that her conviction is brought up to the President as an argument for why the operation should be given the go-ahead. Given what they knew at the time, the best assessment could not have been a 100% chance bin Laden was there. But Maya’s extreme view pulls the group in her direction — perhaps only from 60 to 75%, but enough to tip the scale to that side.

These are the characters we glorify in our culture: those that have the courage of their convictions, that don’t waver even when everyone doubts them, that stand up to the group and are vindicated in the end. But this is a dangerous example to follow. Swing and miss on such a strong argument? You might not even get three strikes before you’re tuned out.

And swing and miss I did. Goodwin, in the end, didn’t live up to my expectations. After four unproductive seasons, he was cut out of training camp this year¹ and has essentially washed out of the league. He’s still incredibly young: Buddy Hield, in his second season, is actually a few months older than Goodwin. But Goodwin never showed any improvement on what he was in college: he still gets to the rim and the line at very high rates, but he still can’t finish, can’t shoot, and can’t take care of the ball.

On the night of the draft I didn’t have particularly high hopes for us being able to grab Goodwin. Neil really seemed to be listening to the concept, but still had strong doubts about whether Goodwin could develop enough to be worth a trade — particularly if we had to move up to the early 20s to get him. The rest of the league, it turned out, had similar doubts and Goodwin kept sliding and sliding, to the point that a trade up for him was possible at relatively low cost. But Neil (correctly, in retrospect) did not believe enough in Goodwin as a player even if he saw the logic of my argument, and so we stayed put. I sagged a bit in my chair watching the Suns scoop up Goodwin with the 29th pick.

I’ve thought about this a lot in the years since. You could argue that I was right, conceptually. That Goodwin was a good gamble that didn’t pay off, the kind I wrote about in A Roll of the Dice, Part 3. But in many ways I did get it wrong. With the benefit of more years of experience, I see the things I missed but shouldn’t have: the ways that the statistical analysis could have been done better, the ways my own scouting could have informed that analysis.

Every year I feel that way. I look back on what I knew and thought the previous year and realize how foolish I was in so many areas. I puff up a bit with pride, as I think about what I’ve learned — until it occurs to me that a year from now I’ll look back on what I think today and see how stupid I was.

The story of my push for Archie Goodwin reveals many of the biggest challenges of front office decision making. How do we properly characterize our confidence in a way that helps the group make the best decision? How do we go against a popular opinion while not feeling exposed? How do we make sure we’re constantly learning, even if it means acknowledging we are constantly wrong?

Scouts across the league are fanning out around the country now, going to college practices and starting to dive deeper into this year’s draft class. It’s the beginning of a long road that ends with precisely these questions.

Last week The Athletic published an excerpt from Jason Lloyd’s book The Blueprint, that discussed the Cleveland Cavaliers’ decision to select Anthony Bennett with the #1 overall pick in the 2013 draft. It included this fantastic quote from David Griffin, who was the VP of Basketball Operations for the Cavs at the time:

“The issue with Anthony was, and we had no way of knowing it at the time, the kid had no desire to overcome adversity whatsoever. As soon as it was hard, he was out,” (David) Griffin said. “His whole life, he rolled out of bed bigger, better, and more talented than everybody else. As soon as it was hard, it was over. And I was the one on campus at UNLV. I’m the one who got sold the bill of goods and I bought it hook, line, and sinker. You f*** up sometimes.

We don’t do this enough in the NBA. We rarely look back on past mistakes, search for causes, and admit fault when it’s warranted. We’ll come up with explanations for why we got it wrong, but often these are exculpatory — stories we tell ourselves and others to keep our reputation intact even in the face of clear blunders. This is a natural defense mechanism against all those who pick at mistakes as evidence of incompetence, but it is a damaging one. Because without an honest assessment of where things went wrong, learning is impossible.

Learning how to properly evaluate players is hard enough on it’s own. As I wrote in A Roll of the Dice, Part 2:

Player evaluation in the draft happens to be a task that is very difficult to improve at. Developing intuition is easiest in a simple, predictable environment where there is clear and frequent feedback. Think about playing a card game or a video game: you get better at it without much effort because the rules are always the same and you find out pretty quickly when you make a good or bad decision.

The draft is the opposite of this: there is a lot that goes into whether a player ends up being successful, the nature of the game is subtly shifting over time, and you don’t often find out the results of your decision for multiple years. It’s almost designed for people to not be able to get better at it. Which is a large part of why there are so many mistakes, and why the league as a whole doesn’t seem to be getting much better at drafting over time.

To have any chance of improving, we need to study our failures. Why didn’t Archie Goodwin work out? Why didn’t Anthony Bennett? Where did our evaluations go wrong? What can we do in the future to make sure it doesn’t happen again?

This goes against attitudes that are embedded deeply in NBA culture. Front offices often encourage being strong and wrong over being weak and right. They view expressions of uncertainty as efforts to dodge the question and avoid going on record. They want more cocksure Mayas, and fewer dithering CIA analysts.

But it shouldn’t be this way. We shouldn’t be afraid of mistakes, because everyone gets the draft wrong. Everyone. If you meet someone who only talks about their successes and won’t admit their failures, just end the conversation — you won’t get anything out of it. The question is not whether someone got something wrong, it’s how often they will get things wrong. And what’s the best way to minimize those future mistakes? By learning from past ones.