I have just had my new closest 2nd place in Itadaki Street DS. It was me, Mario, Peach and Yoshi on the Mushroom Kingdom board (the one shaped like an M).

I was investing in my shops to make money but I had forgotten that Mario was very close to the goal of 18,000 coins. When I levelled up again both me and Mario had exceeded that goal so it was basically a race back to the bank space. Then Yoshi got the Boo chance card, which teleports everyone to that space, which was 5 spaces away from the bank.

If I had rolled a 5 then, I would have won. I threw the die, and it came up on... one. :(

By some coincidence, my total assets added up to exactly 100 coins less than Mario's.