What would you do with the money if you won the lottery? If you would give part to tzedaka, how much, and to which? Discuss.

Aside from the tzedakah aspect, I'd probably set aside funds for my children, etc. and invest a bit.

I would ask my Rav what to do.

I would put it away for at least a month...Only after I've allowed for some time to pass would I make any decisions as to what to do with it. Making decisions like that in the heat of the moment isn't the most smartest thing to do.

Gosh, you have your own brain. If you need to ask anyone it's your accountant.

Anyway, I would first give a percent to charity and have fun putting in to all my favorite causes. Than I would consult my accountant on where to invest etc.

The first thing I'd do is call my grandmother (who is also the family CPA). The next thing I'd do is take some time off work. A week or so and I'd use a few thousand of my existing dollars to go somewhere out of reach. Then I'd dole some money out to my favorite charities and I'd give some money to family members. I'd create some small trust funds for young relatives (to be released when they are 21) that would grow over time. I'd put most of the money out of my reach earning interest. Money is just a tool after all. I'd use it to make doing the things I want to do that much easier.

You have your own brain.

BH my Rabbi has good financial sense. For what percentage to give to tzedaka, I would want to call him. He would also be able to provide me guidance in how to ensure the money doesn't endanger me spiritually.

Depends on the amount, but for this exercise I will assume it's in the millions:

After taxes:
-10% would be put aside for tzedaka right from the start
-pay off all my bills, my parents,my brother's, and a few close friends' bills as well.
-talk to my dad about investments (he's good at that)
-buy real estate (for my home & just land to open up to hikers & campers - no hunting, but maybe fishing)
-start a tzadaka foundation - named after my maternal grandparents - aside from donating to groups/organizations, Jews & non-Jews would be able to write grant requests.

..

how much money are we talking about?

The amount is not important, but for the record, we'll say one hundred million.

Exactly what I do now, except I'd do it in style......

the amount is very important, given the real estate prices in NY

after the taxes and maaser, i would buy a two family house, put away money for my daughter's tuition (school, seminary, college, master's), invest the rest.

Ah, sorry. I wasn't thinking about NY real estate prices.

I'd go on a super deluxe cruise around the world.

I'd give money to worthy causes, including:
Helping kids with terminal illnesses have some enjoyment (like taking kids with cancer to Disneyland.)
Helping OTD young adults from super religious communities get an education.
Helping gay, lesbian and transgender runaway teenagers to get off the street and on the right track (ie get a ged, go to college or get a job, have a normal environment to live in, etc.)
Promoting Japanese language education
Promoting secular democratic values in Israel.

And then I'd keep some money for a rainy day.
End of story.

I'd split the money with my son, my mom, and my brother and his family. That leaves $25 million just for lil' old me. I would:
Buy a nice condo in Montreal (loft with rooftop deck)
Buy a nice condo in Israel (loft with rooftop deck? Sure, why not)
Give a large chunk of it to the following types of causes:
Purchasing and furnishing a nice apartment building to provide supervised housing for people with severe and persistent mental illness (The "nice" part is important - everyone deserves to live in dignity and having a clean, properly-furnished and recently renovated apartment is a significant step up.)
Giving a nice amount to each of my friends at work, so they can go on a vacation, pay down their mortgage or whatever they decide
Support for no-kill animal shelters
Nefesh b'Nefesh
Start a gardening project in the Palliative Care Units of major hospitals

And a couple of "toys" as well...