Fair Trade

Why Jose Canseco Makes Me More Optimistic About AI

You likely don’t remember your first trade.

But I bet you remember your first bad one.

Mine was in 1986. I was seven years old and fully convinced Rickey Henderson was as close to perfection as a human being could reasonably get. He stole bases, hit home runs, and was from Oakland. I mean, have you seen his thighs?

One afternoon at King’s Baseball Cards in Berkeley, I pulled a Donruss Rated Rookie card of a guy named Jose Canseco.

“Funny name,” I thought.

An older kid who knew my taste immediately offered me multiple Rickey Henderson Yankees cards for it. Rickey had become a Yankee, so at least temporarily I had become a Yankees fan too. Multiple Rickeys for one card? What a day. What a pull.

Then a few months and one Rookie of the Year award later, I realized what had happened.

That Jose Canseco Rated Rookie was hot. It became one of the defining cards of the late 80s. Meanwhile my stack of average Rickey Yankees cards quietly sat in my binder like tiny cardboard lessons in market inefficiency. That’s when I first learned about the Beckett Baseball Card Monthly.

Beckett basically told collectors what cards were worth. If you had one, you knew the market. If you didn’t, you were guessing. The older kids always seemed to have one. I didn’t. Because information wasn’t free. And that’s what makes me wonder:

What exactly is a fair trade?

Fairness isn’t only about outcomes and results. It’s about equal access to information. The trade itself wasn’t illegal. The older kid simply knew something I didn’t. I had vibes.

And honestly, that’s how a lot of markets work. The people closest to information usually win. Traders with faster news. Realtors with neighborhood knowledge. Investors with better research. Entire industries have been built around informational asymmetry — one side simply knowing more than the other.

For most of history, information was expensive. If you wanted expertise, you paid for it.

That’s why AI feels potentially important in a deeper way than just productivity or chatbots writing emails. Maybe we have some agency to help AI become the first universally accessible Beckett. Not perfect. Not always right. But available.

Suddenly ordinary people can interrogate systems that previously only insiders could access:

“What questions would an expert ask before signing this?”

“What does the other side know that I don’t?”

Experts will still matter. Judgment will still matter. Some people will always have more money, better timing, or better instincts. But there’s a meaningful difference between losing because someone outplayed you and losing because you never understood the rules in the first place.

The older kid wasn’t magic. He just had information. And maybe the future gets slightly fairer if everybody does.

Money is weird.

Information is weirder.