Sassy Steak Chili

I first made this chili a couple years ago for a church chili cook-off.  I probably went way overboard with excitement over a simple friendly food competition.  I looked up a dozen or more recipes & found one that really stood out to me.  I tweaked it to my likings & I am so pleased with it!  It's hearty with chunks of tender steak, smokey & full of heat, and warming with a hint of sweet.  I ended up winning the award for "BEST Spicy Chili" in our church chili competition; winning a "Chili's" Gift Card for a whopping $10!  But, you know what?  I loved every minute of my little fame.  I think the steak really sets this chili apart from the rest.  Plus it's bold, spicy, mildly sweet & a little sassy!

This recipe is time consuming, but it's worth the effort.  I always get asked for the recipe when we feed our friends this meal, & you will want to share it with your friends because it makes a lot!  That or freeze it for a later meal, which works well too.  Also, this chili may or may not have put one of my friends into labor.  All I know is they came over for my chili dinner one night & she had the baby by the next morning (on her due date!)  Just sayin... this chili is amazing in more ways than one!  Make this for your next tailgate or Halloween party.  It feeds a crowd on the cheap!

*Update 10/30/13: This chili has just won it's 2nd Chili Cook-Off!  BEST Spicy Chili award yet again!  2 for 2!  This is chili is a winner in more ways than one.  I only make it once a year, but I look forward to it every October.  I have also updated the top & bottom photos in this post to hopefully make you excited to try it! :)  

Sassy Steak Chili

Recipe adapted from Jeremy Vohwinkle by: Amber (Dessert Now, Dinner Later!)

• 1 large Green Bell Pepper, medium diced
• 1 large Poblano Pepper, medium diced
• 1 large Sweet Onion, medium diced
• 6 cloves Garlic, minced
• 2 lbs Top Round Steak
• 1 lb roll Jimmy Dean's HOT Sausage
• 1 Tbsp Kosher Salt
• 1 tsp Pepper
• 5 Tbsp (+) Worcestershire Sauce
• 2 Tbsp (+) Hickory Flavored Liquid Smoke
• 1/3 can pureed Chipotle Peppers with Adobo Sauce (about 4-5 peppers)
• 2 (15oz) can's Mild Chili Beans
• 2 (28oz) cans Crushed Tomatoes
• 2 Tbsp (+) Chili Powder
• 5 dashes (+) Tapatio/Tobasco Sauce
• 1 1/2 tsp (+) Cumin
• 1/4 cup sugar

First Day:

1. Chop the peppers & onion, medium dice.  Put chopped vegetables in a LARGE, preferably stainless steel bowl, to prevent staining or flavoring the bowl.  Add minced garlic.
2. Cut the steak into half-inch cubes.  Add to bowl.  Break up sausage into pieces straight into the bowl.  Add kosher salt, black pepper, worcestershire, liquid smoke & chipotle paste.  Rub the marinade through all meat & veggies.  Determine if you need more liquid.  Make sure everything is moist & covered.  I usually end up needing 1-2 Tbsp more liquid, so I'll add extra worcestershire/liquid smoke mixture.  
3. Refrigerate overnight, if possible, but at least 4 hours.

Second Day:

1. After meat has been marinating overnight in the refrigerator, it's time to start cooking.  Give the meat a quick stir to absorb any juices that may have seeped out.  In a large skillet, cook the meat in 3 batches.  If you cram the meat in one pot, it will take longer to cook & you'll end up steaming the meat.  So work in 3 batches.  Each batch will take 7-10 minutes on medium-high heat.  As your meat browns, you'll notice liquid coming out of the meat & veggies, it's fine because that's where a lot of the flavor comes from.  Don't boil it all away, but reduce it a little bit so you don't end up with soup instead of chili; then add meat & liquid straight to a large stock pot.  Continue batches until all meat is browned.  
2. Once all the browned meat is dumped into the stock pot, add the entire cans of chili beans.  Then, add almost one entire can of crushed tomatoes.    Give the pot a stir.  Check the consistency & add more tomatoes, a little at a time, stirring frequently until you reach the desired texture.  It can turn to soup real quickly so go slow when adding the tomatoes.  (I usually end up using 1 1/2 cans for a medium chunky texture.  I like a little bit of liquid to soak up with a breadstick or cornbread.  This particular time I made it using the whole 2 cans, so it would feed a few more people, so it's a little wetter in the pictures than I usually make it.)
3. Now, it's time to season the chili.  Start with 2 Tbsp Chili Powder, 5 dashes of Tapatio/Tobasco, 1 1/2 tsp Cumin, & 1/4 cup Sugar.  It should be pretty spicy from the chipotle peppers, so give it a stir & a taste.  Adjust seasonings as you see fit.  
4. Simmer, covered, for a minimum of 2 hours, but if you have 4 hours, that is the best!  I like to stir the chili every hour or half hour to make sure it's not sticking to the bottom of the pot. (Best to use a non-stick stock pot, if you have one.)  This long, slow cooking process really gives the meat a chance to become very tender, & all the flavors & spices marry beautifully.  Serve with cheese, sour cream, breadsticks/cornbread.  

*Makes at least 1 gallon (16 cups)  
**You can put this chili in the slow cooker!  Marinade the meat overnight, brown the meat in 3 batches, but put the meat in a slow cooker.  Finish the steps as written.  Slow cook on low for at least 4-6 hours.  I did mine for 8-10 & it wasn't over-cooked, still tender & delicious!  I did stir it a couple of times during the day to keep it from boiling too much around the edges.  Enjoy!!!

I first made this chili a couple years ago for a church chili cook-off.  I probably went way overboard with excitement over a simple friendly food competition.  I looked up a dozen or more recipes & found one that really stood out to me.  I tweaked it to my likings & I am so pleased with it!  It's hearty with chunks of tender steak, smokey & full of heat, and warming with a hint of sweet.  I ended up winning the award for "BEST Spicy Chili" in our church chili competition; winning a "Chili's" Gift Card for a whopping $10!  But, you know what?  I loved every minute of my little fame.  I think the steak really sets this chili apart from the rest.  Plus it's bold, spicy, mildly sweet & a little sassy!

This recipe is time consuming, but it's worth the effort.  I always get asked for the recipe when we feed our friends this meal, & you will want to share it with your friends because it makes a lot!  That or freeze it for a later meal, which works well too.  Also, this chili may or may not have put one of my friends into labor.  All I know is they came over for my chili dinner one night & she had the baby by the next morning (on her due date!)  Just sayin... this chili is amazing in more ways than one!  Make this for your next tailgate or Halloween party.  It feeds a crowd on the cheap!

*Update 10/30/13: This chili has just won it's 2nd Chili Cook-Off!  BEST Spicy Chili award yet again!  2 for 2!  This is chili is a winner in more ways than one.  I only make it once a year, but I look forward to it every October.  I have also updated the top & bottom photos in this post to hopefully make you excited to try it! :)  

Sassy Steak Chili

Recipe adapted from Jeremy Vohwinkle by: Amber (Dessert Now, Dinner Later!)

• 1 large Green Bell Pepper, medium diced
• 1 large Poblano Pepper, medium diced
• 1 large Sweet Onion, medium diced
• 6 cloves Garlic, minced
• 2 lbs Top Round Steak
• 1 lb roll Jimmy Dean's HOT Sausage
• 1 Tbsp Kosher Salt
• 1 tsp Pepper
• 5 Tbsp (+) Worcestershire Sauce
• 2 Tbsp (+) Hickory Flavored Liquid Smoke
• 1/3 can pureed Chipotle Peppers with Adobo Sauce (about 4-5 peppers)
• 2 (15oz) can's Mild Chili Beans
• 2 (28oz) cans Crushed Tomatoes
• 2 Tbsp (+) Chili Powder
• 5 dashes (+) Tapatio/Tobasco Sauce
• 1 1/2 tsp (+) Cumin
• 1/4 cup sugar

First Day:

1. Chop the peppers & onion, medium dice.  Put chopped vegetables in a LARGE, preferably stainless steel bowl, to prevent staining or flavoring the bowl.  Add minced garlic.
2. Cut the steak into half-inch cubes.  Add to bowl.  Break up sausage into pieces straight into the bowl.  Add kosher salt, black pepper, worcestershire, liquid smoke & chipotle paste.  Rub the marinade through all meat & veggies.  Determine if you need more liquid.  Make sure everything is moist & covered.  I usually end up needing 1-2 Tbsp more liquid, so I'll add extra worcestershire/liquid smoke mixture.  
3. Refrigerate overnight, if possible, but at least 4 hours.

Second Day:

1. After meat has been marinating overnight in the refrigerator, it's time to start cooking.  Give the meat a quick stir to absorb any juices that may have seeped out.  In a large skillet, cook the meat in 3 batches.  If you cram the meat in one pot, it will take longer to cook & you'll end up steaming the meat.  So work in 3 batches.  Each batch will take 7-10 minutes on medium-high heat.  As your meat browns, you'll notice liquid coming out of the meat & veggies, it's fine because that's where a lot of the flavor comes from.  Don't boil it all away, but reduce it a little bit so you don't end up with soup instead of chili; then add meat & liquid straight to a large stock pot.  Continue batches until all meat is browned.  
2. Once all the browned meat is dumped into the stock pot, add the entire cans of chili beans.  Then, add almost one entire can of crushed tomatoes.    Give the pot a stir.  Check the consistency & add more tomatoes, a little at a time, stirring frequently until you reach the desired texture.  It can turn to soup real quickly so go slow when adding the tomatoes.  (I usually end up using 1 1/2 cans for a medium chunky texture.  I like a little bit of liquid to soak up with a breadstick or cornbread.  This particular time I made it using the whole 2 cans, so it would feed a few more people, so it's a little wetter in the pictures than I usually make it.)
3. Now, it's time to season the chili.  Start with 2 Tbsp Chili Powder, 5 dashes of Tapatio/Tobasco, 1 1/2 tsp Cumin, & 1/4 cup Sugar.  It should be pretty spicy from the chipotle peppers, so give it a stir & a taste.  Adjust seasonings as you see fit.  
4. Simmer, covered, for a minimum of 2 hours, but if you have 4 hours, that is the best!  I like to stir the chili every hour or half hour to make sure it's not sticking to the bottom of the pot. (Best to use a non-stick stock pot, if you have one.)  This long, slow cooking process really gives the meat a chance to become very tender, & all the flavors & spices marry beautifully.  Serve with cheese, sour cream, breadsticks/cornbread.  

*Makes at least 1 gallon (16 cups)  
**You can put this chili in the slow cooker!  Marinade the meat overnight, brown the meat in 3 batches, but put the meat in a slow cooker.  Finish the steps as written.  Slow cook on low for at least 4-6 hours.  I did mine for 8-10 & it wasn't over-cooked, still tender & delicious!  I did stir it a couple of times during the day to keep it from boiling too much around the edges.  Enjoy!!!