Preheat the oven to 425 degrees F. Cut the stalks off the fennel bulb. Cut the bulb in half through the core. Remove the core, then slice the bulb vertically into 1/3 inch wedges.
Cut the new potatoes in half length-wise, then slice them into 1/8 inch semicircles. Lay the potatoes on one rimmed baking sheet and the fennel on another. Drizzle both sheets with oil, then sprinkle with salt and pepper. Toss the potatoes and fennel and spread them out in a single layer.
Roast the fennel for 20-30 minutes. Roast the potatoes for 30-40 minutes flipping once.
Meanwhile, preheat the grill to high heat, approximately 500+ degrees F. Drizzle the steaks with oil, then liberally salt and pepper.
In the blender, puree the shallot, mayo, vinegar, Dijon, 2 tablespoons oil, and honey until smooth. Salt and pepper to taste. Prepare 4-6 plates by piling them with arugula leaves. When the grill is ready, cook the steaks 2-3 minutes per side for medium-rare. Allow the steaks to rest for at least 5 minutes under foil. When the steaks have rested, slice them thinly on the bias.
To plate: drizzle the creamy red wine vinaigrette over the arugula. Place a pile of potatoes on the greens, followed by several slices of steak, roasted fennel, topped with a sprinkling of golden raisins.