FAQ removed - double-checking provenance.

You won’t get Winifred by accident, because she’s sold in her own individual pack. So why would you like her and what should you watch out for?

First, WH is a triumph of theming. Each of the individually sold investigators expand their color, and green is about risk. Some characters, like Nathaniel Cho, are campfires. A few things to get you started, and you can keep it burning all night. Every animal you punch with your boxing gloves will get you more cards to punch more people.

Winnie is an industrial coal boiler. For every two cards you give her, she’ll usually give you back one. Opportunist, most of the time, will cover for you, but if you don’t draw it or you lose it, you’re out of luck. Manual dexterity changes the ratio, and so do other cards like the lucky cigarette case, but most of the time you’re going to need a runway.

There’s another downside: one willpower. You will get screwed over by the encounter deck unless you and your teammates have mitigation. First watch, ward of protection 2, the usual players will need to be in full force to keep you from going insane.

But the rest is upside. Winnifred is one of the best evaders in the game, and unlike Rita or Stella, she can get massively rewarded for it. Pickpocketing is a way of life. Sneak By gives you money while doing what you were going to do anyway. Delilah damages your enemies or Cat Burglars let you strand non-hunters. Nimble will move you around the map, bringing your safeguarded guardians along with you. And once it’s running, your draw engine is one of the best in the game. No other rogue can mill their deck as fast, getting extra actions with quick thinking or dropping a “Watch this” for big cash.

You’re also incredibly flexible. “Anything you can do“ gives you viability in everything, even willpower tests, and with unexpected courage, it’s a success on anything but the autofail and a free card. Scenario cards that test books, fists and/or feet are much less of a challenge for you.

Just avoid failing! Unlike a survivor, you don’t get second chances at skill tests. Your engine can sputter out with a few bad pulls. When that happens, don’t be afraid to take a few actions to draw cards, knowing that when you’re on top again, you’ll have bonus everything.

The aviatrix has natural synergy with mystics who can help her predict the future. Jacqueline with premonition, scrying mirrors, or triple token pulls is great foil. So is Anyone who can fill the bag with bless tokens, turning even hard pulls into succeed by two opportunities.

Insane. It’s very easy to trigger her reaction 2 times in a turn, and to succeed by a lot besides.

Winifred’s biggest drawback is that it can be difficult to find tests to over-succeed with. In a group setting she therefore excels in a similar role to Finn, by engaging that one most problematic enemy and keeping them occupied Wini can turn a poorly located enemy into a repeatable source of cards such that evasion isn’t as big a sink of actions as it might be for other characters. In a solo setting Wini needs Lockpicks up right away so that she can reasonably commit her Opportunists to a number of tests without losing them. The end result of this is a draw machine that rivals even Minh.

Of the Mono-color investigators she is quite easily the best, with access to a card pool which complements her strengths, but she does struggle with Willpower tests. For this you will probably want to hold onto a couple guts and maintain a healthy respect for which tests you can fail without major problem.

Take her for a spin, you won’t regret it.

For those asking "what core investigator role is Winifred best suited for: Fighter or Cluever?", it appears that she is capable of being built as either one. Similar to Jenny Barnes and Finn Edwards, the Rogue card pool can make Wini into a Cluever (Lockpicks, Lola Santiago) or into a Fighter.

As a Fighter, she can be built in two different ways:

Option 1 - Agility. Built similarly to Finn's fighting style, trying to leverage her Agility (Ornate Bow, Sneak Attack, Backstab).

Option 1 - Strength. Now with Lonnie Ritter and Delilah O'Rourke as part of the card pool, Wini could be a gun-wielding Fighter as well due to these allies bringing Wini's Strength to 5.

Sharpshooter is an interesting card that helps either of these two combat options. Wini now gets to attack using her Agility score instead (which would be 5, instead of attacking at 3 Strength).
Added to Option 1, any Agility boosters would make this even better (The Moon • XVIII, Lola Santiago, Cat Burglar).

If added to Option 2, with Lonnie and Delilah, then Wini would be at a base of 6 Agility, and attacking using that rather than her base Strength of 5. Sharpshooter would also give a +2 bonus from the two Strength boosts that each ally provides. So Wini would be shooting a gun with a combat skill of 8, plus the bonus from the weapon she is using. Pretty good! Checkout my review of Sharpshooter if you'd like to unpack the topic more.


So, what role is Winifred best suited for? I'm going to vote Fighter.
Fighting usually requires high skill tests, and you are rewarded more for over-committing to these tests than compared to clue gathering. Also, a lot of the Rogue weapons reward you for over-succeeding, so you might as well play Wini this way. Otherwise, why are you playing an over-succeed investigator? What's the payoff?

What do you think? Is Wini's "optimal" build to be a Fighter, or a Cluever?
Feel free to share details about strategies and cards that help bolster her "optimal" role.