I brought 11,258 shares of TSFG in total in 2009 for $16,495.84 and later in 2010, tsfg was taken over to TD (Toronto Dominion Bank Ltd) and all TSFG shares were convereted to TD shares which were valued for $2,2220.28. I sold them in November 2010 for a mere profit of $2.37. I am at loss of $14,243.00. How to file taxes for this. I appreciate your help.

Please clarify: how much did you receive when you sold the TD shares? Was it $2,220.28 +$2.37 = $2,222.55? If so, then you have a loss of $16495.84 -2,222,55 = $14,273.19. You report this loss on schedule D as sale of TD shares first acquired in 2009. This assumes that the takeover of TSFG by TD was a tax-free exchange of stock for shareholders (which this type of deal usually is). One minor complication - if you received any cash in lieu of partial shares then that cash represents a return on a portion of your original investement, and you should also report that. If you can give us some more details on whether the exchange included any cash to you we can walk you through how to report it.

**EDIT - please see my follow up post **

Update - please ignore my previous response as I found this information about the exchange:
http://phx.corporate-ir.net/External...xUeXBlPTM=&t=1

The exchange of shares was actually a taxable event. Therefore you report the sale of TSFG shares and your gain (or loss) is the difference between the value of stock received plus cash in lieu of any fractional shares less your original investment. So on Schedule D you report a sale of 11258 shares of TSFG for a loss of $16,495.84 - $2220.28 = $14,275.56. (This assumes you received no cash; please provide details if you did. You should have received a 1099-B form that provides the exact numbers to use.) Then you sold the TD shares for a gain of $2.37, which you report as a separate transaction on Schedule D.

In Form 1099-B, I see the below values:
2: Under #2:Stocks, bonds, Etc reported to IRS
-- Gross proceeds less commissions and Optins Premiums: 10,372.49
5: No of shares exchanged : 13,128

Those numbers don't agree with what you wrote before. You said the TD shares you received were valued at $2220.38, but the 1099-B says they were valued at $10,372.49. It also says you exchanged 13,128 shares of TSFG, not 11,258. From these numbers it appears you should report a loss of: $16,495.84 - $10,372,49 = $6,123.35 on the swap of TSFG shares. Then when you report the November sale of your TD shares you use a cost basis of $10,372.49.

Below are full details of 1099-B
1a:Date of Sale or Exchange : See Details
1b: CUSIP No: See Details
2 : Under #2:Stocks, bonds, Etc reported to IRS
-- Gross proceeds less commissions and Optins Premiums: 10,372.49
4: Federal Income Tax Withheld : 0.00
5: No of Shares Exchaged : 13,128
6: Classes of Stocks Exchanged: See Details
7: Description : See Details
Regulared Futured Contracts
8: Profit or (loss) realized in 2010: 0:00
9: Unrealized profit or (loss) onopen contracts - 12/31/2009: 0:00
10: Unrealized profit or (loss) on open contracts - 12/31/2010: 0:00
11: Aggregate profit or (loss) 0:00
Details of form 1099-B-proceeds from broker and barter exchange transactions:
Note: Pl copy and past the below details into excel sheet for clear view:
Date Description symbol CUSIP # Shared Exchanged Class amount federal tax withheld No loss if checked
Line#1a Line #7 Line #1b Information Line #5 Line #6 Line #2 Line #4 Line #12
4/12/2010 ambac financial abk 23139108 sell 1,825 C 3,822.44 0
10/6/2010 tsfg 837841105 taxable reorgs 11,258 c 3,236.85 0
toronto domini td 891160509 sell 45 o 3,313.20 0


Total: 13,128 10,372.49

OK - you have three transactions to report on your Schedule D:

1. Sale of Ambac Financial: 1825 shares for $3822.44. You haven't asked how to report that, so I assume that you have no issues there.

2. Sale of TSFG: 11258 shares for $3236.85. Your cost basis was the $16495.84 that you mentioned previously, for a loss of $13,258.99.

3. Sale of 45 shares of TD for $3313.20, using a cost basis of $3236.85 for a gain of $76.35.

Yes Sir!