To kvell or not to kvell, that is the question.
On one hand, Luis de Carabajal y Cueva was pretty darn awesome. How many other Jewish conquistadors can you name? Yet that's what Carabajal was — alright, he wasn't too Jewish himself, as his parents were forced to convert to Christianity. Still, once you get past that, a Jew who roamed the Atlantic in charge of a fleet, a Jew who explored new lands (he was the first Spanish subject to set foot in what is now Texas), a Jew who governed the Mexican state of Nuevo Leon, a Jew who helped bring other Jews to North America... That's some kvell. That's a lot of kvell.
On the other hand, Carabajal started out as a slave trader. And he massacred many, many Native Americans. Yep... not much kvell there.
Carabajal didn't exactly end well. He was living in Mexico, supposedly as a good Christian, when the Inquisition (no one ever expects the Spanish Inquisition!) decided to intervene. Carabajal and his entire family were charged with "Judizing", jailed and tortured. He died in prison; his relatives were burned at the stake.
Somehow, that gives us a little more reason to kvell...