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   Selected Articles by Twenty-First Securities Authors


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:



"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.



Gordon, Robert and Fichtenbaum, Mark, “End-Run Around Constructive Ownership Rules Fails," Journal of Taxation of Investments, Civic Research Institute, Vol. 28, No. 2, Winter 2011

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.

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.

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.

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.



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

Gordon, Robert, and Lyman, Charlotte "Hedging Your Employee Stock Options (Part 2)," Mystockoptions, Brookline, MA.

Gordon, Robert, and Lyman, Charlotte "Strategies For Hedging Concentrated Stock Positions (Part 1)" MyStockOptions, Brookline, MA.

Gordon, Robert, and Lyman, Charlotte "Strategies For Hedging Concentrated Stock Positions (Part 2)," MyStockOptions, Brookline, MA.

Gordon, Robert, and Lyman, Charlotte "Strategies For Hedging Concentrated Stock Positions (Part 3)," MyStockOptions, Brookline, MA.

Gordon, Robert and Rosen, Jan, "The Benefits and Methods of Harvesting Your Losses, and Not Just at Year-EndThe 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.



Gordon, Robert, and Stanaslovich, Louis, “TRAKRS: A Tax Efficient Substitute For Hedge Funds and Other Investments Risk-Controlled Investing, Charter Financial Publishing Network, Shrewsbury, New Jersey, August 2006  



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).

Gordon, Robert, and Trotta, Stanley "Stock Options: How Tax Rate Changes Impact Strategies for Stock Options & Restricted Stock," MyStockOptions, Brookline, MA.



Gordon, Robert, "The 21st Century Solutions to Hedging Low-Basis Stock", The Journal of Wealth Management, Institutional Investor, Vol. II No. 4, Spring 2009

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.

Gordon, Robert, “A Few Words About DividendsOn 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).

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.

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.

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.



Gordon, Robert, "Are Deferrals Worth It?",  InvestmentNews, June 30, 2008, Robert Gordon's monthly column, "The Tax-Conscious Adviser"

Deferring into a higher tax rate only makes sense with double-digit returns or long time frames.



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?



Gordon, Robert, "Commodities ETFs Can Be Taxing,InvestmentNews, January 30, 2011, Robert Gordon's monthly column, "The Tax-Conscious Adviser"

With these complex products, an unexpected tax bill may arrive.



Tailored
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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.

Gordon, Robert, “Commodities in An Asset Allocation Context Journal of Taxation of Investments, Civic Research Institute, Kingston, New Jersey, Winter 2006

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.



Gordon, Robert, "Convert Roths Early In the Year", Twenty-First Securities'  newsletter, Tailored Solutions
Volume XI, Issue 3, Fall 2009



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.

Gordon, Robert, “ETFs: Facts and Fictions Risk-Controlled Investing, Charter Financial Publishing Network, Nov./Dec. 2005 



"ETNs Under the Microscope" Currency ETNs are debt, other ETNs are open for comment.   Op. Ed. in InvestmentNews.

Gordon, Robert, “Fees, Taxes and ETFsWealth Manager, Highline Media LLC, July/Aug. 2006

Gordon, Robert, “Going ForwardWealth Manager, Highline Media, May 2006



Gordon, Robert, "GRATs: The Time Is Now", InvestmentNews, October 4, 2009, Robert Gordon's monthly column, "The Tax-Conscious Adviser"

If Obama has his way, grantor remainder annuity trusts will become less attractive



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.

Gordon, Robert, “Harvest Your Capital Gains? Private Wealth Management, CFA Institute, June 2008



Gordon, Robert, "Harvesting Losses with Options", InvestmentNews, November 21, 2008, Robert Gordon's monthly column, "The Tax-Conscious Adviser"

There are ways to take losses with minimal disruption to alpha.

Gordon, Robert, “Hedge Funds In Mutual Fund Clothing: The Best of Both Worlds?” Risk - Controlled Investing, Charter Financial Publishing Network and Wealth Advisor Publishing, October 2005

This article was based on a winter 2005 newsletter article.

Gordon, Robert, "Hedging Your Employee Stock Options (Part 1)," MyStockOptions, Brookline, MA.

Gordon, Robert, "Hedging Non-qualified Stock Options," Journal of Taxation of Investments, Civic Research Institute, Kingston, New Jersey, Spring 2004.

A discussion of the two primary challenges that executives must address before hedging non-qualified options: the constructive sale rules and the potential for a whipsaw effect.

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.



Gordon, Robert, "How to Start the Year Off Right", InvestmentNews, January 2, 2011, Robert Gordon's monthly column, "The Tax-Conscious Adviser"

Also, new mutual fund tax rules and the end of a Social Security free lunch.

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.



Gordon, Robert, “Investing In Offshore Hedge 
Funds - Taxation Issues
Risk-Controlled Investing, Charter Financial Publishing Network, Shrewsbury, New Jersey, August 2006



"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.

Gordon, Robert,  "Is Your Hedge Fund a Trader or an Investor?" Journal of Wealth Management, Institutional Investor, New York, Summer 2005



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?

Gordon, Robert, "The Magic of ETNs," InvestmentNews, July 9, 2007, Robert Gordon's monthly column, "The Tax-Conscious Adviser"

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.

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.

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.



Gordon, Robert "Making Most of Excess Capital Losses", InvestmentNews, March 8, 2010, Robert Gordon's monthly column, "The Tax-Conscious Adviser"

Here are some ways to create gains through timely sales of fixed-income investments.

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.



Gordon, Robert, "The Most Tax-Efficient Way to Own Gold",  InvestmentNews, March 7, 2010, Robert Gordon's monthly column, "The Tax-Conscious Adviser"



Tailored
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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.

Gordon, Robert, " New Commodities Vehicles: How Markets Responded to Rev. Rule 2006-1," Journal of Taxation and Regulation of Financial Institutions, Civic Research Institute, Inc., New York, Jan./Feb. 2007

An investor can add substantial value by utilizing the commodities product that offers the best combination of low cost and positive tax treatment.

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.

Gordon, Robert, "Options Can Be Handy When Working Within The Wash Sale Rules," On Wall Street, Thomson Media, New York, November 2004

Here's how to use them.



Gordon, Robert, "Passive vs. Active for the Taxable Investor", Investment & Wealth Monitor, Nov./Dec. 2010 

Gordon, Robert, "Recent Developments Involving Hedges, Collars and Microsoft Dividends," Journal of Taxation of Investments, Civic Research Institute, Kingston, New Jersey, Winter 2005

Seven year hedges OK, plus good news on closing profitable hedges with profitable stock and insiders' ability to collar their employee options.  Dividend capture scenarios. 

Gordon, Robert, "The Rich Are Different," On Wall Street, Thomson Media, New York, October 2005

And they want to hear different ideas.

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.



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.

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.

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.



Gordon, Robert, "Stealth Taxes", InvestmentNews, April 7, 2008, Robert Gordon's monthly column, "The Tax-Conscious Adviser"

 How stealth taxes impact investor costs



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.

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.

Gordon, Robert, “The Tools of the Trade On Wall Street, Thomson Media, New York, December 2005

Gordon, Robert, “Uncommon Retirement Wisdom  
On Wall Street
, Thomson Media, New York, June 2003

The benefits of tax deferral?



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.



Gordon, Robert, "When Is A Dividend Not A Dividend", InvestmentNews, May 3, 2010, Robert Gordon's monthly column, "The Tax-Conscious Adviser"

Sometimes a distribution turns out to be a return of capital, which has its advantages.

 

 


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