If a company goes private, does it still count as a capital gain/loss?
does it still count as a capital gain or loss? Yes. Is it essentially treated like you sold the stock at the price of the buy-out?  Yes. Do you still get a 1099-B from your broker? Yes.
The loss for B can be used to write off the gain for A.  You will fill out a schedule 3 with cost base and proceeds of disposition.  This will give you a $0 capital gain for the year and an amount of $5 (50% of the $10 loss) you can carry forward to offset future capital gains.  You can also file a T1-a and carry the losses back up to 3 years if you're so inclined.  It can't be used to offset other income (unless you die). Your C and D trades can't be on income account except for very unusual circumstances.  It's not generally acceptable to the CRA for you to use 2 separate accounting methods.  There are some intricacies but you should probably just use capital gains.   There is one caveat that if you do short sales of Canadian listed securities, they will be on income account unless you fill out form T-123 and elect to have them all treated as capital gains. I just remembered one wrinkle in carrying forward capital losses.  They don't reduce your capital gains anymore, but they reduce your taxable income.  This means your net income won't be reduced and any benefits that are calculated from that (line 236), will not get an increase. "Individuals most definitely can have NOL. This is covered in the IRS publication 536. What is the difference between NOL and capital loss? NOL is Net Operating Loss. I.e.: a situation where your (allowable) expenses and deductions exceed your gross income. Basically it means that you have negative income for that year, for tax purposes. Capital loss occurs when the total amount of your capital gains reported on Schedule D is negative. What are their relations then? Not all expenses and deductions that you usually put on your tax return are allowed for NOL calculation. For example, capital loss is not allowed. I.e.: if you earned $2000 and you lost in stocks $3000 - you do not get a $1K NOL. Capital losses are excluded from NOL calculation and in this scenario you still have non-negative income for NOL purposes even though it is offset in full by capital loss deduction and your ""taxable income"" line is negative. The $1K that was not allowed - gets carried forward to the next year using the Capital Loss Carryover Worksheet in the instructions to Schedule D. You calculate your NOL using form 1045 schedule A. You can use the form 1045 to apply the NOL to prior 2 years, or you can elect to apply it only to future years (up to 20 years). In what cases, capital loss can be NOL? Never." "The way the post is worded, coca cola wouldn't count towards either, although it's not entirely clear. If the dividends are considered under capital gains (which isn't technically an appropriate term) he's earning only 500Million a year from his stake in coca cola. If he sold his shares, he'd receive capital gains of ~15Billion, which would probably outpace his operations business.   The best graph would probably be something like ""net worth of operations vs net worth of equity in other companies""" The short answer is no - the CGT discount is only applied against your net capital gain. So your net capital gain would be: $25,000 - $5,000 = $20,000 Your CGT discount is $10,000 You will then pay CGT on $10,000 Of course you could sell ABC in this financial year and sell DEF next financial year.  If you had no other share activities next financial year than that net capital loss can be carried forward to a future year. In that case your net capital gain this year would be $25,000 Your CGT discount is $12,500 You will then pay CGT on $12,500 Next year if oyu sell DEF, you'll have a $5000 net capital loss which you can carry forward to a future year as an offset against capital gains. Reference: https://www.ato.gov.au/General/Capital-gains-tax/Working-out-your-capital-gain-or-loss/Working-out-your-net-capital-gain-or-loss/ I don't know about the liquidation. The capital doesn't evaporate, its source just becomes the corporation itself. The corporation becomes the sole shareholder and acts at the behest of the board. The board then decides both board matters and shareholder matters.  Once I talked that through, I realized no one would do this. If the board is in complete control, why clump the ownership together. The directors would be better served by clearly delineating their ownership interests by purchasing shares directly. "I think the key concept here is future value.  The NAV is essentially a book-keeping exercise- you add up all the assets and remove all the liabilities.  For a public company this is spelled out in the balance sheet, and is generally listed at the bottom.  I pulled a recent one from Cisco Systems (because I used to work there and know the numbers  ;-) and you can see it here: roughly $56 billion... https://finance.yahoo.com/q/bs?s=CSCO+Balance+Sheet&annual  Another way to think about it: In theory (and we know about this, right?) the NAV is what you would get if you liquidated the company instantaneously.  A definition I like to use for market cap is ""the current assets, plus the perceived present value of all future earnings for the company""... so let's dissect that a little.  The term ""present value"" is really important, because a million dollars today is worth more than a million dollars next year.  A company expected to make a lot of money soon will be worth more (i.e. a higher market cap) than a company expected to make the same amount of money, but later.  The ""all future earnings"" part is exactly what it sounds like.  So again, following our cisco example, the current market cap is ~142 billion, which means that ""the market"" thinks they will earn about $85 billion over the life of the company (in present day dollars)." How you are taxed will depend on what kind of stock awards they are. The value will be determined by the company that issues it, and appropriate tax forms will be sent to you to include with your taxes. The way the value is determined is an accounting question that is off-topic here, but the value will be stated on your stock award paperwork. If you are awarded the stock directly then that value will be taxed as ordinary income. If you are awarded options, then you can purchase the stock to start the clock on long-term capital gains, but you will not incur any tax liability through the initial purchase.  If the company is sold privately and you have held the stock for over 1 year, then yes, it will be taxed as a long-term capital gain. If you receive/exercise the stock less than 1 year before such an acquisition, then it will be considered a short-term capital gain and will be taxed as ordinary income. No. You're entitled to 1% of votes at the shareholders' meeting (unless there's class division between shareholders, that is). If more than 50% of the shareholders vote to close the company, sell off its assets and distribute the proceeds to the owners - you'll get 1% share of the distributions.