Steak Sinatra, a variation on steak pizzaiola, appears on many menus in the Palm Springs, California area where Mr. Sinatra used to reside. Most of the restaurants that serve it claim it was Frank's favorite dish, even though the recipes vary widely, some are downright awful, and it is doubtful that Mr. Sinatra ever ate in many of those establishments. This recipe comes from a restaurant called Leon's, now defunct, although the chef, Leon, is still active in the area. While Leon doesn't claim that he served Mr. Sinatra, this recipe is the best I've tried.
Figure on half an hour cooking time plus chopping time (2 minutes for Jacques Pepin, more for the rest of us). The recipe will serve 4 male teenagers or up to 8 seniors.
An authentic Caesar salad starter course is a perfect accompaniment to steak Sinatra.
2 Lbs Tender steak such as tenderloin or New York strip
Salt and pepper
2 Cloves garlic, sliced
1/4 Cup EVOO
1/2 Onion, sliced
1/2 Green bell pepper, large dice
1/2 Red bell pepper, large dice
1/2 Cup Red or white wine
1 Can Italian San Marzano tomatoes D.O.P. on the label
1 Tbs Demi-glace
2 Cloves Garlic, pressed
1 Tbs Dried oregano
1/2 Tsp Red pepper flakes (optional for heat)
4 Oz Mushrooms, cut bite-sized
4 Oz Frozen or packed-in-water artichoke hearts
2 Oz Black olives, pitted and halved (optional)
1 Lb Penne or similar dried pasta
Chopped Italian parsley for garnish
Cut the steak cross-grain into strips 1/4 - 3/8" thick and about 1.5" long. Season them with salt and pepper. Heat half the EVOO in a large skillet or sauté pan, add one of the sliced garlic cloves and cook until the garlic browns. Discard the garlic. Sauté the steak slices in the garlic-flavored oil until just browned (about 2 minutes) in at least 2 batches. Be careful not to overcook. Reserve the steak in a warm oven.
Add the rest of the EVOO to the pan and sauté the onions and bell peppers until the onions are golden, about 5 minutes. Add the wine and deglaze the pan. Add the tomatoes, hand-crushed, with half the liquid in the can, the demi-glace, remaining sliced and pressed garlic, oregano and red pepper flakes. Add salt and pepper to taste. Cook 15 minutes, uncovered, until the sauce thickens. Add the mushrooms, artichokes and olives and cook an additional few minutes. Return the steak to the pan and cook just long enough to heat everything through.
The sauce needs to be just the right thickness, neither too thin nor too thick. Add a little more liquid from the tomato can if needed. If it is too thick, thin with a little wine.
About halfway through the sauce making process, cook the pasta in rapidly boiling salted water for 10-12 minutes, depending on how al dente you want it. Drain the pasta and add it to the pan. Toss well, sprinkle with chopped Italian parsley for garnish and serve. I like to drizzle a little EVOO over the finished dish.