Yes, Tony's grandfather was a stone mason, and there is a scene in the first season where he proudly takes Meadow into a church that his grandfather built. However, Tony is quite ambivalent about his humble origins. The second dream last night was more of a nightmare than a wish fulfillment. Tony is living in the "twilight of the godfathers," a theme that weaves in and out of all four seasons. He isn't making it, and his successor is hooked on Vitamin H and is in rehab after a highly unorthodox "intervention." So, one view of the dream is that Tony is feeling like a failure. He wanted to stand on the shoulders of his ancestors and be a success in upper-middle-class terms with all the external trappings—$2 million house, SUV, daughter at Columbia, etc. Instead, he now finds himself in the same position as his immigrant grandfather who is a blue-collar joe with blisters on his hands. He reassures himself at the end of the episode by standing on the deck of the luxury hotel and looking out at the ocean.