Pre-heat oven to 375°F. Heat the pickling liquid over medium-high heat in a medium-size saucepan and add the hubbard squash ribbon. Simmer until tender, about 5 minutes. Set aside to cool in the liquid.
In a medium-size roasting pan, toss the kabocha squash wedges with salt, pepper and a drizzle of olive oil. Roast until tender in the oven, about 15 minutes. Set aside.
Whisk together the vinegar, honey and grated garlic in a large salad bowl and slowly add in the remaining 1/4 cup olive oil until emulsified.
Tear the kale into bite-size pieces and toss together with the pickled squash, roasted squash, blanched squash, radish slices, radish greens, cilantro and pepitas in the salad bowl with the dressing. Lace a few slices of ham across the top and enjoy.