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In the first pages of Dragon Heist, you're told to

When you run this adventure, you choose its main villain at the outset. Your choice determines the season of the year in which the story takes place, as well as the antagonists in several of the encounters in chapter 4.

While multiple places in the book specify you can switch villains at any point.

You can swap out one villain for another at any time.

If you switch to a new villain midway through the adventure, don't change the season to match.

The problem is, there aren't any guidelines to choosing the villain. I've read the first 3 chapters, and so far there are only allusions to Xanathar's and Manshoon's (in the gang war of Xanathar VS Zhentarim). There is a brief allusion to the Cassalanters in a Force Grey mission about the Black Viper, and there is also a mission to visit Jarlaxle in his ships at some point.

So, what are good guidelines to choosing the villain at the outset? Should it depend on what my players are expecting? Or on their alignments? Or just something fun for me to DM?

My thought process so far is to either go Xanathar or Manshoon, since those are the most familiar to PCs for most of the story. But even then, I only came to that conclusion after reading a few chapters, and I'm not sure if I should read the book in its entirety before starting the campaign.

If there are no official guidelines to this question, please back up your answers with your own experience.

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Each of the villains has their own flavor, and each suits a different style of play. It's worth reading the Play Style chapter of the DMG (page 34) and considering which suits your group, then reading the chapters relevant to the four villains to see which suits your campaign style best. In loose terms, Jarlaxle is intended as a swashbuckling anti-hero with a bit of a spy-movie feel, Manshoon is a villainous mastermind at the center of his well-defended lair, and The Xanathar is an eccentric and sometimes darkly humorous oddball character.

It's worth considering that the Summer story arc with the Cassalanters as villains is, by design, a tough moral dilemma to face the party with. To quote Dragon Heist co-designer James Haeck from an article in DnD Beyond:

The most horrific moment of the entire story happens when the player characters make a no-win choice at the end of the Cassalanter storyline.

This refers to the fact that the plot driving the Cassalanters as villains is built around

a sort of Trolley dilemma, where the party's success in the scenario dooms two children, while their failure or inaction dooms 99 strangers.

In light of all that, pay special attention to list of questions on page 34 of the DMG, and compare them against the 4 villains presented. Answering those questions will help guide you to the right choice for your group.

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  • \$\begingroup\$ You know what would be great? A mapping of the 4 villains to the items in the DMG on page 34. \$\endgroup\$
    – Kreakdude
    Commented Mar 26, 2020 at 4:57
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I do not have any official rulings on this but in my past experiences the most notable way to choose a villain is to determine the season and that will determine the villain. One of my DM's rolled a d4 and let that choose: 1=Spring, 2=Summer, 3=Fall, 4=Winter. There doesn't seem to be any set "right way" to choose a villain. Realistically the campaign can be played with each season to have four different outcomes. The alignments of your party does not need to be a factor in choosing and the player expectations (for most of the players I've seen) is to have Xanathar as the villain. You are the DM, make it what you want.

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    \$\begingroup\$ This is a way to do it, but it doesn't really answer the question. The OP is seeking guidelines on how to choose, depending on player expectations, alignments, etc. \$\endgroup\$
    – JohnP
    Commented Jun 18, 2019 at 14:03
  • \$\begingroup\$ @JohnP I was answering in regard to the final statement in his question. \$\endgroup\$
    – Eternallord66
    Commented Jun 18, 2019 at 14:08
  • \$\begingroup\$ Honestly, I would have thought the Zhentharum would be the more obvious villains. Particularly since the events in chapter 3 make mark them as the Bad Guys citywide. If they end up being the villians, there's basically no story twist at all moving into the last chapter. \$\endgroup\$
    – T.E.D.
    Commented Aug 14, 2019 at 19:16
  • \$\begingroup\$ Useful answers answer the whole question itself rather than one sentence of it. \$\endgroup\$
    – SevenSidedDie
    Commented Nov 10, 2019 at 17:23
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Dragon Heist, to be honest, is my favorite Mod out atm. I have run it 3 times and getting ready to run it the 4th time. Each time with a different villain. I would say read the book and take the time to think about what your players would enjoy. The villain doesn't come into the game for real until later in the story, so you can always pick your villain after the first couple of games, so that you can see how your players are planning on playing the game and take the villain that would be most enjoyable for them and yourself.

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  • \$\begingroup\$ This answer doesn't really provide anything new in comparison to the much older and already accepted answer. Do you have a new or different viewpoint or analysis on each villain? \$\endgroup\$
    – T.J.L.
    Commented Jan 16, 2020 at 14:05
  • \$\begingroup\$ Hi Craig, welcome to the site! You may want to take the tour: rpg.stackexchange.com/tour \$\endgroup\$
    – Raj
    Commented Jan 16, 2020 at 14:29

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