I think it's time we take another careful look at Leo de Luca. The general opinion on this card shifts heavily as new cards and new investigators are released, but I'm going to attempt to distinguish exactly what makes this card good, why so many people run him, and when it is smart not to run him.
Here's what makes Leo good. Leo is an Ally, with 2 damage soak and 2 horror soak. He gives you one extra action every turn as long as he's out, and he costs 6 resources. On a baseline level, one would say he pays for himself if you were to take 5 or so "gain a resource" actions in 6 turns (if we value his soak for 1 resource and 1 card, which to me is fair). Now if you only get 5 actions out of this guy a game, arguably those actions were on average more valuable to you than "gain a resource" actions, so as long as you are willing to trade resources for tempo, Leo is a great card to run. Assuming you get him out early enough and keep him alive long enough that he nets you more than 5 actions, then he becomes amazing tempo, and really this is what you shoot for. Most people who run Leo will choose to always run two just to increase the chance of seeing him in the opening hand.
In particular, his ability makes him shine in true solo. A single action a turn for one investigator in 4 players is a pretty minuscule boost unless you're someone who's actively handling enemies for everyone, but in true solo it's almost akin to buying 33% more turns. In fact, it's better, because 4 actions a turn means 1 less Mythos Phase per every 3 turns (12 actions would have been 4 tests, now it's 3), which means at optimum you're looking at 25% less Mythos Phases. That's an important thing in true solo, where being bogged down by enemies is a common way for a scenario to just end, and Rogues in particular have the lowest average in the game, so tests hurt them quite a lot as well.
The trap with Leo is his cost: Six resources. Even if you're playing true solo, you shouldn't automatically take Leo thinking he's going to make your game easier every time. Like anything else in a card game, you're looking at opportunity cost- what in Leo's place could you have run that may have also saved you actions? For example, if I'm Zoey Samaras, that Beat Cop is both going to increase my such that I pass tests I might not normally pass, saving me an action each time it does, and it can swing for 1 damage in a pinch so I don't have to waste time, say, engaging a Whippoorwill. Plus since he's 2 resources cheaper, I can spend that on a weapon much sooner than I otherwise would have been able to, like Enchanted Blade. Or say I'm Sefina Rousseau, where I'm running lots of spells and events. It might be stronger for me instead to invest in David Renfield who can both generate resources I need to play lots of events and boost my in such a way to make my spells hit more often. The thing is, until you get Charisma, it isn't really valid for most investigators to run Leo in a deck with other Ally assets, as once Leo hits the table, you have to do whatever you can to keep him there. One of the investigators I mention at the end of this review is a major exception to this.
So when considering whether or not to take Leo, the single most important thing to ask yourself is whether or not you have a way to pay for him. If you can afford him without delaying everything else you want to play too much, he's a great choice. Fortunately, Rogue has a myriad of ways to help you afford Leo. Hot Streak, Another Day, Another Dollar, even the upgraded Leo De Luca which merely costs 1 resource less (so you can play him first turn every time without taking a resource). Cards like Lone Wolf and Investments can help you recoup the cost after you've played Leo as well. And finally, you should more strongly consider him in true solo, where actions give you more bang for your buck (caveat: in multiplayer it hurts less to have one investigator down on resources for a while, so the cost is lower in multi while the benefit is higher in solo). So who should take Leo most often?
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Preston Fairmont - Leo is practically made for him. He start with 9 resources, and he gets 5 to spend every turn. Both poor and rich builds can easily afford Leo. It is worth noting that extra actions in Preston will often be less valuable, as he can't just spend an action expecting to pass any old test. Instead extra actions in Preston have to be used for economy- either to pull resources off of FI, generate more resources to spend on things like Intel Report or Lola Santiago (with Charisma), or to refill your hand to have more things to spend on later turns. Here Leo is just an insane economy generator for Preston whose fleeting resources can be turned into permanent economy. I still say you should run Leo pretty much every time in Preston.
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Wendy Adams - Wendy, like Preston, has access to the best two pools in the game for generating resources. Take Heart and Drawing Thin go a long way on their own to reducing the opp cost of using Leo, while Lone Wolf can pull its own weight just fine, especially in solo. Additionally, Wendy's token mitigation means that a stray test here or there is less likely to be a waste, so actions in general are more valuable for her than most. The only Ally competing for her attention in my opinion is Peter Sylvestre, whose +1 is handy for Wendy's defensive events like Waylay, Backstab, and Sneak Attack. This will depend on how you build Wendy, but my advice is to take Peter Sylvestre 2 and Charisma as early upgrades, but start with Leo.
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Leo Anderson - Ah yes, Leo + Leo, a match made in heaven. Leo Anderson can play an Ally at the beginning of his turn at a 1 resource discount, and he has access to other Rogue level 0 cards. Outside of all of that though, a Leo Anderson deck is already running Calling in Favors and later Charisma, so if you don't get Leo in your opening hand, you might be able to Favors him into play from some Beat Cop or Guard Dog on the brink of death. This is the only time I'd run Leo with any other Ally in the same deck at level 0.
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Tony Morgan - The new Rogue on the block needs a little time to get started, but his action economy is wild. Free actions for fighting, then you take shenanigans like .41 Derringer, Quick Thinking and Ace in the Hole. Make up the cost using Pay Day, and use Ever Vigilant and Another Day, Another Dollar to get started. You'll find that it wont be hard at all playing Chicago Typewriter alongside Leo, and the actions you earn can be used for fighting, positioning, or banking for later a la Borrowed Time on a really important Typewriter test, for example.
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Jenny Barnes - This one shouldn't be too surprising. Jenny decks are a common home for The Louisiana Lion, and with Jenny's double income it's not hard to see why. She can recoup the lost resources very quickly, and her even stat-line means that there's less of a chance that an extra action couldn't be put to some sort of use. She can do it all, and Leo just helps her do it all 33% more. The only thing is Jenny has access to all level 0 cards, so an Ally like Leo is competing against Dr. Milan Christopher, Beat Cop, and most notably Mr. "Rook".
I also want to outline a few investigators where Leo might look really appealing but is often (not always) a terrible choice:
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"Skids" O'Toole - Skids' native ability is already about turning resources into actions. Sure Leo gives him the opportunity to take 5 action turns, but you really need to be generating tons of resources for it to be worth running both, alongside all the other things you need to be doing. Skids' usefulness a la Chicago Typewriter has also greatly diminished thanks to Tony Morgan, so I recommend taking Alice Luxley alongside Scene of the Crime and Intel Report, or consider Venturer with Ornate Bow as your main weapon.
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"Ashcan" Pete - A lot of what applies to Wendy in regards to economy still applies to Pete, but the problem is Pete already has solid action compression from Duke. It's usually cheaper and more action efficient to utilize Pete's Ally slot and off class slots to make Duke's actions better. This means using your off class slots for things like Magnifying Glass to make Duke's investigate & move better, and using your Ally slot for someone like Madame Labranche who can keep your hand full to toss more cards to ready Duke. I would say the off slot is also too precious for all the other Dunwich investigators: Zoey needs things to help her investigate like Sixth Sense and Drawn to the Flame; Rex needs some means of defense like Fire Axe; and Jim is too asset heavy to begin with to run another Ally, especially if he's using Dr. Elli Horowitz or Mr. "Rook".
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Finn Edwards - My personal opinion is that Finn Edwards benefits more from Peter Sylvestre. It both gives him a boost to , his favorite stat by far, and lets him soak horror from failed Rotting Remains tests. An argument could be made for Leo with Charsima, especially as a means to mitigate impossible to pass Terror cards like Frozen in Fear, but if you're really worried about that you might as well just take Logical Reasoning. In fact, if you want cheaper action compression, you can reliably activate Track Shoes on most turns, and even if you don't you'll love the extra .
I want to add a special note here that none of these are a hard rule. Deckbuilding requires innovation, planning, and the consideration of a ton of variables including: player count, investigator choice (yours and your compatriots), specialization vs generalization, campaign, upgrade path, opportunity cost, and even theme and desired play style. The above investigators I mention as being apt to take Leo are the ones who, on a baseline level, can either deal with the cost the easiest or take advantage of his ability the most, or both. The ones who I mention as not necessarily being a good place for Leo are ones where I see him commonly run to little effect. I do not think however that a Finn or Skids deck, for example, cannot work with Leo de Luca. It's up to you, the player, to determine how best to utilize each investigator's ability, and whether or not Leo de Luca gets you there.