Either the car or thimble. Although it didn’t matter as I have never in my life won a game of Monopoly. Even when I cheated, I still managed to lose.
Always the hat…Always
The car or the top hat, but in the end it didn’t matter, because I’d always lose anyway.
Today’s Medium Large seems appropriate. 
I was the dog or the car. My brother, who beat me religiously, was the guy on the horse. My wife says she was the iron.
Good grief! I must be older than dirt. I’m sure I was always a white wooden milk bottle. Have I imagined such a thing?
Toto
Battleship. Always battleship and heaven help anyone else who lays hands on it. I also cheat. A lot. To me cheating is more fun than winning.
mm
I’ve always liked the battleship. If I can’t get that (and now, my eight-year-old son grabs it first, just to mess with me 
), I’ll go for the racecar.
I really *want * the battleship, though, dammit…
Wow, how the memories come back!
Shoe or Wheelbarrow, sometimes Scottie Dog, until the arrival of Dead Junebug.
Dead Junebug was the slumlord King of Mediterranean and Baltic Avenues, piling on the ramshackle tenement hotels, until the fateful day he circled tooooo close to the lamp next to Dad’s barcalounger, ricocheted off and hurtled down to destroy the entire neighborhood. All his desiccated legs cracked off, hurtling through the streets of Monopolyland, his irridescent torso spinning wildly toward Broadway, rolling over the fancy hotels and unsuspecting tourists.
It was never about the money to me…
I always tried to be the car. If that was taken, I’d grudgingly take whatever was left after everyone else had selected their pieces.