No.
Yes. A gentle touch of cinnamon is quite nice (and also a typical Mexican spice, although I grant that chili is usually more Tex-Mex, depending on how you make it.)
Yeah, nothing wrong with a little cinnamon. I don’t put it in my chili, but there’s no particular reason to avoid a pinch of it.
And by ‘chili powder’, I’m assuming you mean ground ancho or NM chilies and the like, not the chili powder mixes that you find in the spice section.
Rather than cocoa, I usually drop a couple of squares of dark chocolate in the pot. I’ve used cinnamon in the past, but it’s a powerful spice and easy to overdo, so I usually skip it.
Chili powder means Gebhardt’s.
I emailed Tito’s. Their recipe is a ‘closely-guarded secret’. They hinted I should dump the cumin. (But I like cumin!)
How much for, say, three pounds of chuck?
I often add the remains of the morning coffee pot for some liquid for the summer. I use red wine (a solid malbec works well) rather than beer when deflating after growing the cow.
All started when In was after some condiment ideas to go with a new years evening goat grilling. Someone here had a great recipe for a chilli paste involving coffee. Used it ever since. It adds and certain eathiness to the chilli.
Also if the chilli comes out a little ‘thin’ just rest it for the day and reheat.
.
+1
As for “how much,” the recipe on the back of my container of Gerbhardt’s says 1 tablespoon per pound of beef, along with 2 teaspoons of cumin. I personally think this is WAY too little. I go for more like 2-3 tablespoons of chili powder per pound of beef. That’s basically about 2/3 of the entire 3 oz container of Gerbhardt’s. I would personally say use 7 tablespoons of it, plus 2 tablespoons of cumin for three pounds of beef.
Too much ain’t enough.
No, I mean the spice blend, not powdered chiles. (Although, like I said in the quote, you can make your own.) To me, “chili powder” (spelled with the “i”) means a blend of powdered chiles, cumin, and whatever other chili herbs and spices you like (onion powder, garlic powder, maybe oregano.) If I’m rolling my own, I usually do a mix of Hungarian sweet paprika (for color and sweet pepper flavor), ancho chile powder, guajillo chile powder, and then some “sharper” chile like cayenne or arbol or pequin for the heat. (Though usually I have some dried Thai chiles from the garden that I use in this regard). Maybe even habanero powder if I’m in that kind of mood. (Though, honestly, as much as I love habaneros, I really don’t like the habanero flavor so much in chili.) Oh, and sometimes dried chipotle peppers, too, for a bit of smoke. The idea is sweetness and pure (non-spicy) red pepper flavor from the paprika, a bit of depth and fruitiness from the ancho, some earthiness and heat from the guajillo, sharpness and punch from one of the little hot peppers (arbol/pequin/cayenne/Thai), and then maybe some smoke from the chipotle. On top of that, garlic powder, onion powder, and a touch of Mexican oregano. I’ll sometimes add other spices, but the chili powder blend I like to keep fairly simple and add whatever additional accent spices (like cinnamon or more Mexican oregano) later.
Sorry, too many people in my life have confused a “pinch” or “gentle touch of cinnamon” as meaning a teaspoon of it.
Maybe I’m too Tex-Mex, but cinnamon in my chili is too close to Cincinnati Five Way Chili, which I find to be an utter abomination. It isn’t even something I would consider decent spaghetti sauce.
Cinnamon on my toast? Cinnamon in my pastries or in my cocoa? Cinnamon in food from the sub-continent? All are fine. But NOT in my chili.
OK, that’s helpful. I hope it really is good, 'cause I just bought six jars! ($34.99, 1.94/ounce, or $5.83/jar. I’ll have to see if they have it in bulk at Cash & Carry.) I’ll still do the bitterness experiment with the dried chiles I’ve been using, but processed powder would be much easier.
When I got home from Seattle last night (surprising The Wife with a dozen roses, a card, and an antique Sniffles figurine for our 2nd anniversary – which she forgot), the chili was on the stove. So obviously, the bitterness isn’t that bad. But if I can avoid it with the powder, so much the better – even if it does go against my ‘make it from scratch’ fixation.
Like I said, if you want to scratch that do-it-from-scratch itch, you can always just roll your own and create your personal chili powder blend using the ingredients I mentioned above. Or if you google, you’ll find tons and tons of recipes. It’s fun, like making your own masalas for South Asian dishes!
As for Gerbhardt’s, it’s the only commercial chili powder I use. You can of course get some fancy schmancy gourmet blends, but for me it’s either I make my own or use Gerbhardt’s (or even a combo of the two.) It is the definitive Tex-Mex chili powder in the way that Old Bay is the definitive Chesapeake Bay seasoning or Hellman’s/Best Foods is the definitive commercial mayonnaise or Lea and Perrins is the definitive Worcester sauce.
I had you figured for a mix your own kinda guy. I buy individual spices from a spice shop down the street, which guarantees their (relative) freshness. A lot of canned stuff can sit on a shelf for a long time. Ground ancho, chipotle, smoked paprika (or California/Hungarian sweet, or both), cayenne, Mexican oregano, cumin, etc. I throw in fresh jalapenos, sweet bell pepper, poblano, garlic, etc. I don’t skimp on the spices. I had to school my sister, who was adding a teaspoon of chili powder to a pot of her “famous” turkey chili. Famous for being bland, perhaps. 
Amen. Before I started using my current recipe, my favorite chili was my aunt Anitia’s recipe. You started with a whole box of Gebhardt’s chili powder and 5-6 dried cayenne peppers. My wife mixes her own like you do, and I usually use that when I’m using a chili powder mix - but if I’m buying any, it’s still Gebhardt’s.
I should mention that I do actually use a commercial mix from time to time, which is Penzey’s Chili 9000, a really unique blend of spices.
I think I remember you posting this before. Basically looks like chili powder meets curry powder and a touch of mole. I used to do a version of chili way back when where I’d essentially do a normal chili recipe and throw in a dab of whatever Patak curry paste I happened to have around. Works pretty well, too.
So I have my Gebhardt’s. I still have a 48-ounce potato salad tub full of the chili I made last week, so it will be a little while before I use the powder.
I might make a smaller batch next time. If 2 oz. powder for 1 lb. beef is the ratio, then 4 oz. powder (1⅓ jar) sounds right for 2 lb. beef. So here’s what I’m thinking: Brown the 1" cubes of chuck as in the OP. Add the Gebhardt’s, cumin, onion, and garlic, and… liquid. Should I use beef broth? Water? A couple bottles of PBR?
Use the beer. Thicken with masa.
Gebhardt’s is Wonder-powder.
Regal chili powder has good reviews.