The Gentleman Joe

What we have done here is refined an American staple, Sloppy Joe’s and renamed them “The Gentleman Joe”.  A bit more involved than your sloppy joe, but to me well worth the work. This is dish makes great leftovers and can go in a lunch for a sandwich or frozen for another meal. A great idea is to double it and then you can put some away for a few weeks from now when you don’t feel like cooking. This is a great meal to put in the crock pot, so you can put if together in the morning and it can be all ready when everyone is starving at dinner time.


1 3-4 lb chuck roast

Kosher Salt and pepper to taste

3T olive oil

1 medium sweet onion chopped

1 T chopped garlic

4T tomato paste

4T vinegar

3T Worcestershire sauce

1T mustard

1T paprika

1 cup red wine

1 cup beef broth (you may need more broth as it cooks)

2T brown sugar

1T soy sauce

Pretzel Roll or Hawaiian Sweet Roll (Or roll of your choice)

Provolone Cheese (optional)



  • Heat olive oil in bottom of pan you are using (I have a crock pot that I can put on the stove top so this is what I use)
  • Cover the meat with salt and pepper and brown in the oil, turning to get both sides. Remove from pan.
  • Add garlic and onion and sauté until tender, but not browned.
  • Add the tomato paste, vinegar, Worcestershire, mustard, and paprika, stir around so flavors are well combined. Be careful not to burn so reduce heat while doing this.
  • Add the wine and broth and bring to a boil, add brown sugar and soy sauce.
  • Add meat back in and make sure it is well covered with the liquid, if not add more wine and/or broth.
  • Put crock pot on low and cook away (or put in oven on low and cook for 1-2 hours checking frequently to make sure there is enough liquid)
  • Shred up and put on sandwich roll
  • Serve with some coleslaw (or our corn salsa…recipe coming) and you are all set.