This is a damn good question. I don't know any anti-bitcoiners who've made good cases for why Bitcoin could fail. I just see the usual refuted FUD coming from anti-bitcoiners.

I know this doesn't exactly answer your question, but I've heard a few couple podcasts from Bitcoiners who are concerned about the community becoming overconfident. They presented some cases where Bitcoin could fail or just fail to meet our expectations. Here are the episodes if you want to check them out:

• Stephan Livera Podcast episode 332 "The Bearish Case for Bitcoin"
• What Bitcoin Did "Beyond Bitcoin Maximalism"
• Bitcoin Audible Read 613 "Against the Inevitability of Bitcoin"

There are some different categories of critic that I think are worth following.

The most overtly anti Bitcoin critic out there who is intelligent is Nassim Taleb. Yes there’s a whole history there, and I think he’s driven by something personal with regards to his Bitcoin stance, but I will say that I still learn from him even when I disagree with him. His “black paper” made me realise even more deeply how immutable the Bitcoin ledger is - because it was probably the most sophisticated critique I’d seen, it got me to understand how he was misapplying ergodicity, and how Bitcoin is abstracted from the specific technology implementing it.

Then there are the skeptics who are well informed, not anti Bitcoin, but not promoting it either. George Selgin comes to mind here if you’re keen on learning about the banking system.

Then there is the type of critic who is pro Bitcoin in theory, but skeptical in practice because they think it has already been co-opted by Wall Street. Here I’m thinking of Ben Hunt if Epsilon Theory - check out his essay “In praise of Bitcoin”.

Finally, I think some of the best Bitcoin critics are Bitcoiners themselves. People who come to mind with good critiques of the tech, the ecosystem, and the culture: John Carvarlho; Shinobi; Pete Rizzo; Aaron van Wirdum.

I had to broaden the scope of your question to get some names - there really aren’t that many anti-Bitcoiners worth following!

Whether any are a good follow, I couldn't tell you but some names in that list include:

• Frances Coppola (journalist, thus has economic incentive to be anti-bitcoin)
• Peter Schiff (sells gold, thus bitcion is a competitor in the store of value asset class)
• Alex De Vries / @Digiconomist (central bank staffer, will spin whatever he can to persuade you that bitcoin mining is bad)
• Cas Piancey and Bennet Tomlin, Crypto Critics Podcast
• Tim Swanson / @OfNumbers

in addition to the usuals, published here:

A guide to Bitcoin critics and sceptics
https://www.redbull.com/int-en/theredbulletin/bitcoin-critics-arguments

And hundreds of authors who have published a "bitcoin is doomed / dead" article:

From Bitcoin Obituaries - "Bitcoin is Dead" Declared 400+ Times
https://99bitcoins.com/bitcoin-obituaries/

I tend to listen to grant Williams, mike green, crypto critics podcast, they sometimes make great points worth considering

The one's that believe in all the values of bitcoin but continue to be incentivized to shill gold or some other fiat service...forever fighting the truth not wanting to accept the fact that they are wrong....If they did in doing so would drive them crazy going their whole lives believing the greatest ponzi of all time!

Only sheeps follow...

https://i.postimg.cc/x8XJcbyv/BTC-haters.jpg

Whether any are a good follow, I couldn't tell you but names in a comprehensive anti-bitcoin list will include:

• Frances Coppola (journalist, thus has economic incentive to be anti-bitcoin)
• Peter Schiff (sells gold, thus bitcoin is a competitor in the store of value asset class)
• Alex De Vries / @Digiconomist (central bank staffer, will spin whatever he can to persuade you that bitcoin mining is bad)
• Cas Piancey and Bennet Tomlin, Crypto Critics Podcast
• Tim Swanson / @OfNumbers

in addition to the usuals, published here:

A guide to Bitcoin critics and sceptics
https://www.redbull.com/int-en/theredbulletin/bitcoin-critics-arguments

And hundreds of authors who have published a "bitcoin is doomed / dead" article:

From Bitcoin Obituaries - "Bitcoin is Dead" Declared 400+ Times
https://99bitcoins.com/bitcoin-obituaries/

Seriously, by now you should have some kind of basic standards on who you follow.

If they can't even grasp the importance of bitcoin, why give them any space at all in your head?

Ray Dalio isn't a Bitcoiner but has Bitcoin in his portfolio for maximum diversification.

He is pretty well known in the traditional finance world. His last two books looked into constants in economics since the dawn of civilization which was pretty insightful (although a little suggestive and clickbaity I think...)

Peter Schiff

Peter Schiff

Although he rails against Bitcoin, I suspect he's less agin' it, than pro his long time shiny rock schtick.

He's good to consider, at least to learn how he rhetorically cheats to make a case. His criticism so often applies to his own baby, gold, and when he stoops to derivatives like GBTC to find fault, you know he can't do better against the real thing.

• @kelseyhightower, at least for a while, but at some point his opposition gets tiring.