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Her money manager is a family friend of her son, which doesn't necessarily mean much. But, her statements show publically-traded stocks that do show typical selling prices for the ones I know or notice. And, it's a tight-knit Jewish community, so I'm not going to try to butt in when I don't suspect anything and know her son watches over her account. She's been making great money for 25-50 years and more. It's her only income. Raised a son, bought a home in Fairfield County, donates to musical charities, travels, lives a good life, pays her taxes, covers her increasing medical expenses in her old age, etc. Her son was paying per trade at a discount brokerage, but moved over to his friend and pays percentage of his assets now.

I would add that almost everyone has had big gains since March 9, 2009. Energy funds have gone down for about a year, but about everything else has done very well for the past six years. We have been in the third longest bull market in history. Yes, we heard the record scratch sound in August, but a pineapple could have successfully managed funds during the past six years. http://money.cnn.com/2015/08/25/investing/stocks-market-in-5-simple-charts/ http://money.cnn.com/2015/05/06/investing/stocks-market-3rd-longest-us-bull-market/

"Although, my client who's paying the most has huge returns all the time and has for years even when all my other clients had losses, so her manager is probably worth his fee." RED FLAG!!! Is her manager Bernie Madoff? The same thing has happened in lesser firms--fake statements showing gains, year after year. It's probably not your job, but someone has to look into this.

Well, that's definitely more than six years, so good for her. I think they say that the stock market has historically gained about10% a year, on average. Of course, we all know what that means: not much to an individual. Maybe nobody got 10%.

I would not assume that the amount shown on the 1099 is fmv. Per RIA CHECKPOINT: Even though fair market value of an item is usually considered the price that a willing seller and a willing buyer would agree to, the Tax Court has taken special factors into account in determining the fair marketvalue of awards and prizes. Where it is obvious that a prize winner may not be able to resell the prize for as much as the contest sponsor paid for it, resale value at the time of receipt, not cost, determines the amount of income.43 Value to the winner44 or cost to the payor45 may also be used as factors. 43McCoy, Lawrence W, (1962) 38 TC 84138 TC 841, acq 1963-2 CB 5.44Turner, Reginald, (1954) TC Memo 1954-38TC Memo 1954-38, PH TCM ¶54142, 13 CCH TCM 462.45Wade, Nathan, (1988) TC Memo 1988-118TC Memo 1988-118, PH TCM ¶88118, 55 CCH TCM 413.

In essence, schirallicpa simply asked if the taxpayer could deduct $4,000 since, if he doesn't, he will pay tax on $20,000 when he only got $16,000. He didn't say the client was hounding him to take a loss, or even if the client was the one wondering about it. I don't really see a reason to call the boat winner greedy here. It's a good question. Can he pay tax on $16,000 since that's what he got? Well, sounds kind of reasonable to me, especially if this all happened within one tax year. I understand the rationale for the question and don't see any reason to assume anybody is greedy because they want to reduce their tax liability if they can legally do so.