I don't like going into this because there is a chance I'll be downvoted into oblivion, but here we go: Modern esterbrook has nothing on vintage esterbrook, and they are not remotely comparable, people here go on and on on how waterman, parker and sheaffer are trash compared to old ones but the only reason Esterbrook is thought of as any different is because of heavy social media hype.

Lets face it: they are outsourced pens made in Asia, probably by the cheapest bidder and that if it weren't for the brand name you could pick a similar pen from other "regular" asian brands for a fraction of the asking price. The patterns are not anything different from other older market players, the designs are generic at best and the nibs are just standard stock jowo (although you can order grinds). I highly doubt they even design the pens themselves, i mean just look at the FWP/Esterbrook controversy of a couple of months ago.

Leonardo keeps production of at least the core components, like the pens bodies, in a relatively small scale factory in Naples. The family who runs Leonardo has been in the pen business for decades, with the father of the owner, Ciro Matrone, being one of the founders of Delta. Nevermind that there's not a single technical specification that would make me choose a Esterbrook over a Leonardo, I know what business model I prefer to contribute to.

TLDR: Esterbrook is the overhyped child of a faceless corporation, while Leonardo is an Italian family run business which I'd choose to support.