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These features are provided for information purposes
only. They are not intended as a solicitation or to provide
specific financial, legal or tax advice. Certain aspects of these
articles may have been rendered inaccurate by events that have
occurred since the articles were published. Investors should consult
with their advisers before taking any action in connection with
the topics discussed herein.
Some of these articles make reference to options. Options
involve risk and are not suitable for all investors. Before engaging in an options transaction, investors
must review the options disclosure document
Characteristics and Risks of
Standardized Options.
To order articles that are not
available online, you can send us an e-mail or you can call us at
212-418-6000.
A Summary of Articles:
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"Straddle
Rules 25th Anniversary",
Calvin,
James N.,
Carlisle, Linda E., Conlon, Stevie D., Ensminger, John,
Fichtenbaum, Mark, Gordon, Robert,
Hammer, Viva, Kaufmann, John, Keinan, Yoram, Kleinbard, Edward D., Leeds, Mark H.,
Maddrey, Jeffrey, Nave, David R., Nijenhuis, Erika, Nirenberg,
David Z., Paul, William M., Rosenthal, Steven M., Sheppard,
Lee A., Stevens, Matthew A., and Weisbach, David
Twenty-First invited the leading minds to weigh in on problems
caused by the straddle rules. The resulting article
(from 20 authors) was printed in tax notesฎ, Dec. 21, 2009.
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Gordon,
Robert, and Fichtenbaum, Mark, "Hedging Appreciated
Employee Stock Options: Tax, Economic and Regulatory Concerns," Derivatives Report,
Warren, Gorham
& Lamont, RIA Group: New York, October 2000
Non-affiliates wishing to hedge
highly appreciated employee stock options should undertake an
analysis to decided which hedging tool to use: swaps, options
themselves, or forward contracts.
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Gordon,
Robert and Fichtenbaum, Mark, "Practitioners
Are Concerned About Proposed Regulations On Exempt Qualified
Covered Call Options, Interest And Expense Capitalization,"
Derivatives Report,
Warren, Gorham & Lamont, RIA
Group, New York, May 2001
Proposed regulations under
Section 1092 would help investors, but a second set of proposals
under Section 263 would hurt. Also, a recent Field Service Advice
raises a red flag for investors entering into prepaid variable
forward contracts involving appreciated securities.
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Gordon,
Robert and Fichtenbaum, Mark, "The
Pursuit of Dividends After the Tax Act of 2003: Limitations,
Traps and Ambiguities,"
Journal of
Taxation of Investments, Civic Research Institute, Kingston, New
Jersey, Autumn 2003
The 2003 Tax
Act reduced the rate of tax on dividend income earned by
individuals to a maximum of 15%. But in order to pay the lower
rate, investors must ensure that they comply with all the
attendant rules.
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Gordon,
Robert, and Fichtenbaum, Mark, Tax
Consequences of Using Listed Equity Derivatives in Managing A
Stock Portfolio, Derivatives Report,
Warren, Gorham & Lamont, RIA Group, New York, July/Aug. 1996
Using
derivatives to hedge stock portfolios can affect the tax
treatment on the disposition of positions, and the
short-against-the-box proposal may require rethinking of some
standard techniques.
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Gordon, Robert and Hoopingarner, Kirk,
"The
Estate Collar", Trusts & Estates, December
2008
Volatile markets call for clever solutions so that,
after a death, estates can profit from upswings--or downswings
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Gordon,
Robert and Rosen, Jan, "The Benefits and Methods of
Harvesting Your Losses, and Not Just at Year-End, The
Journal of Wealth Management, Institutional Investor, Inc.,
New York, Fall 2001
Unrealized losses are an asset
that investors should harvest systematically year-round to achieve
the highest after-tax returns.
Investors who harvest their losses should consider
employing the double-up forward conversion, which should allow
them to avoid both a wash sale and additional market risk.
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Trotta,
Stanley with Gordon, Robert, "Stock
Options", MyStockOptions, Brookline, MA,
April 2009.
How Tax Rate Changes Impact Strategies for Stock Options and Restricted
Stock (Part 1).
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Gordon,
Robert, A Compelling
Option, On
Wall Street,
Thomson Media,
New York, January 2005
Mutual funds that employ hedge
fund strategies offer better tax efficiency than regular funds.
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Gordon,
Robert, A
Few Words About Dividends, On
Wall Street, Thomson
Media,
New York, June 2004
Why you should look more closely
at foreign dividends, MGM's special dividend and preferred
"dividends" (which may actually be interest).
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Gordon,
Robert, A
Tax-Efficient Spin on Futures,
On Wall Street, Thomson Media, New York, February 2004
Individuals investing in TRAKRS,
Merrill Lynch' s new product, can achieve long-term holding period
after only six months and a day.
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Gordon,
Robert, A
Year-End Strategy, On
Wall Street, Thomson Media, New York, December 2003
Investors may convert long-term
losses to short-term; also, investors with underwater short
positions can harvest losses while retaining the economics of the
short position.
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Gordon,
Robert, An Extraordinary Dividend
Opportunity," On
Wall Street, Thomson
Media,
New York, September 2003
Some dividends are large, but
not too large to disqualify them for special tax treatment.
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Gordon,
Robert, "Best
Place For Growth Stocks", Twenty-First
Securities' newsletter, Tailored Solutions - Considered
Responses, Vol. IX, Issue 4, Fall
2006
Are
IRAs the best pocket for growth stocks?
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Tailored
Solutions
version
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Gordon,
Robert, Commodities:
An Asset Allocation Perspective, Risk-Controlled
Investing, Charter
Financial Publishing Network, Shrewsbury,
NJ, July 2006
This article was originally published in Twenty-First
Securities' spring 2006 newsletter.
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Gordon,
Robert, Consider Taking Profits on Your
Bonds, On
Wall Street, Thomson
Media,
New York, December 2002
If you've held a profitable bond
for more than one year, it may make sense to sell it and buy it
back.
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Gordon, Robert, "Drawing
Down Retirement Money" Twenty-First
Securities' newsletter, Tailored Solutions,
Vol. X, Issue 1, Spring 2008
Conference to consider
tax-efficient ways to manage withdrawal of assets.
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Gordon,
Robert, ETFs:
Facts and Fictions, Risk-Controlled
Investing, Charter
Financial Publishing Network, Nov./Dec. 2005
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Gordon,
Robert, Going
Forward, Wealth Manager,
Highline Media, May 2006
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Gordon,
Robert, "Harvest
Your Capital Gains?", Twenty-First
Securities' newsletter, Tailored Solutions,
Vol. X, Issue 2, Summer 2008
Do the math when considering paying taxes now
rather than later.
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Gordon,
Robert, "Hedging
Non-qualified Stock Options Revisited,"
Journal of
Taxation of Investments, Civic Research Institute, Kingston, New
Jersey, Summer 2004.
A follow-up to "Hedging Nonqualified
Stock Options" (spring 2004), this article discusses the
potential impact of two recent developments: Treasury's proposed
regulations governing the taxation of swaps and a separately
issued private letter ruling to a taxpayer who wished to identify
a transaction as a hedge under Section 1221. |


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Gordon,
Robert, "Inside the Dividend
Proposal," On
Wall Street, Thomson Media, New York, March 2003
Whether or not the president's
proposal gets enacted, now is not the time to change portfolios.
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"IRA
Wash Sale Issue Clarified"
An investor who purchases shares in their IRA that were recently
sold for a loss DOES trigger the wash sale rules.
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Gordon,
Robert, "Losses
on an ETF",
February 2009
Is there a way to take my loss on an Index ETF without
having to exit the index and NOT trigger the wash sale rules?
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Gordon,
Robert, "The Magic of
Swaps," On
Wall Street,
Thomson Media, New York, April 2003
This institutional tool offers
many advantages for affluent individual investors.
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Gordon,
Robert, "Make the Most of Capital
Losses,"
On
Wall Street, Thomson Media, New York, May 2003
Here are some strategies to
unleash the value of this hidden asset.
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Gordon,
Robert, "Making Hedge Funds More
Tax- Efficient,"
Journal of Wealth Management, Institutional Investor,
New
York, Summer 2004
A
discussion of tax strategies for hedge fund managers and
investors. At the
portfolio level, tax management should involve holding period
strategies and trading strategies (such as loss harvesting).
At the investor level, tax management may involve
derivatives on hedge fund indexes, simple call options on hedge
funds themselves and insurance wrappers.
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Gordon,
Robert, "Microsoft's Big
Dividend," On
Wall Street, Thomson Media, New York, October 2004
The software giant's policy
change has raised several questions among investors. Here
are some answers.
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Tailored
Solutions
version
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Gordon,
Robert, Mutual
Funds: Gain Without Pain, Risk-Controlled
Investing, Charter
Financial Publishing Network, Shrewsbury,
New Jersey, March 2006
This article was originally published in Twenty-First
Securities' winter 2006 newsletter.
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Gordon,
Robert, "The New Tax Law and
You," On
Wall Street, Thomson Media, New York, July 2003
Forget simplicity. Chasing
dividends while hedged can be quite complex.
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Gordon,
Robert, "The
Rich Are Different,"
On
Wall Street, Thomson Media, New York, October 2005
And they want to hear different ideas.
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Gordon,
Robert, The Right Way to
Utilize Wall Street Research,
The Philadelphia Stock Exchange, Philadelphia, PA, Vol. 1, No.
2, July 1994
Industry forces are often
responsible for much of a stock price's movement. By purchasing
recommended shares and simultaneously "shorting" the
industry, an investor can often mitigate the effect of an industry
downturn.
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Gordon, Robert, "Selling
Covered Calls", Twenty-First
Securities' newsletter, Tailored Solutions - Considered
Responses, Vol. X, Issue 2, Summer 2008
Investors can reap the rewards of selling covered
calls without ever delivering their low-basis shares.
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Gordon,
Robert, "Single Stock Futures and
Taxes,"
On
Wall Street, Thomson Media, New York, January 2003
This new tool can be a great
hedging device, but the tax consequences can be tricky.
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Gordon,
Robert, "Spiders,
Schmeiders," On
Wall Street,
Thomson Media, New York, February 2003
Get indexing's benefits a lot
less expensively (and with better tax treatment) through Index
options.
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Gordon,
Robert, "Structured
Notes", Twenty-First
Securities' newsletter, Tailored Solutions, Vol. X, Issue
1, Spring 2008
Build Them Yourself: Lower costs and better tax treatment
are possible if an adviser goes solo.
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Gordon,
Robert, Taxing
Phantom Hedge Fund Profits, On
Wall Street, Thomson Media, New York, August 2004.
Many hedge fund investors wind
up paying tax on more profit than their investment actually
earned. How to ensure you pay tax only on what you make.
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Gordon,
Robert, "When
ETFs Pass Along Gains", Twenty-First
Securities' newsletter, Tailored Solutions - Considered
Responses, Vol. X, Issue 1, Spring 2008
While ETFs can minimize taxes, there are caveats.
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