Calvin Wright in the Key of Y

Let me first say that I don't think Calvin is the best investigator. It takes effort to bring him just in line with other investigators, only to then be lot closer to death. However, he is also utterly Arkham Horror. The tension of marching straight up to the death line and toeing it for the rest of the game is awesomely fun. He requires a change of mindset from how you'd normally play. Rather than reacting to encounters and mitigating damage as best you can while progressing the acts as efficiently as you can, Calvin gets fired up by eating encounters and finding enemies to bloody him up a bit in the early game. It's all a little backwards.

Alright, the deck. The key synergies here are Meat Cleaver, Petey, and Painkillers. The Cleaver and Painkillers can help damage and horrify you early if the encounter deck doesn't do it, and then they're how you manage your imminent death for the rest of the game. You want to hover at 4-5 damage & horror. You've got free Leather Coats and Cherished Keepsakes to soak up excess later. If you get too close on health you can pop a Painkiller and have Pete talk you through it, and the Cleaver itself can pull a sanity back in a pinch. Just never keep both at 5 for fear of direct damage/horror, unless you have Until the End of Time out or some damage cancellation in hand.

"But what's the deal with the Backpack, isn't that a bad card?", I hear you asking. Well, where this deck gets bananas is when you swap the Key of Ys in for the Keepsakes. +1 to skills for each damage/horror on yourself, and +1 to ALL skills for each horror on the Key which you can easily feed with the Cleaver and Painkillers?! You should have no trouble getting to base 7-8 skills across the board. That's nuts. So, regarding Backpack: In addition to the deck coincidentally being more than 1/3 items, finding the Key early is pretty important, especially if you are abiding by the Taboo list (in which case drop a Keepsake, btw). It does work nicely with the rest of the items, though. Ideally you have a Cleaver and Lantern out, but the Shovel is very decent early if that's all you've got as the +2 to hit helps early and you can always ditch it for a free clue when you draw into your other items later. You obviously can't throw the Coat down with the Backpack out, but you don't need the Coat for damage soak until later in the game when you've already incurred some damage yourself. So it's a nice bonus to have those late-game cards thinned out of your deck.

Upgrade paths are pretty straightforward: Five of Pentacles and Key of Ys immediately, then upgrade Peter Sylvestre and Lucky!. Those alone will likely take you past the halfway point of a campaign so whatever else will be situational. Blood Eclipse would be awesome, unless you've already suffered more than a point of physical trauma. You could replace Perseverance with other damage cancelers like Devil's Luck or even "I've had worse…". Will to Survive (I'd prefer this over Against All Odds) and upgraded Rise to the Occasion are also good choices. Timeworn Brand looks good on paper, but I'm leery of its cost (especially since it'd only be especially helpful early) and in a normal campaign I think it's likely you'll have better things to buy for your remaining scenario or two.

I've only included a single Perseverance. With the amount of soak, Peter, and the Painkillers (remember you can trigger these freely during any player window!), I just don't think you're going to almost-die very often. If I draw it then I'll hold on to it and play a little more fast and loose. If I don't, it means I'm drawing other stuff to keep me alive instead and I'll just let the deck work like it's supposed to. But I don't want a game where 2 of them are clogging up my hand. The idea is to get near death and stay there, not to recursively die.