Loopholes Through The Ages
By Brian O'Keefe

(FORTUNE Magazine) – Over the years Americans have taken a variety of tacks--dipping, dodging, hedging, and kvetching--when it comes to taxes. But there's one thing we all have in common: Everyone hates them. Hey, isn't avoiding taxation what got this great nation started in the first place? Of course, after the Founding Fathers kicked out those tariff-happy redcoats and set up their own government, what did they do first? Enact some taxes. Seven decades later Abe Lincoln introduced the income tax to finance the Civil War. It was repealed after ten years but came back for good in 1913 with the passage of the 16th Amendment. Ever since, looking for loopholes has been as American as writing off Mom (extra dependent) and apple pie (business lunch). Individuals have borrowed a few corporate shelter strategies and vice versa. Our ever-changing code has been reviewed, reformed, and rewritten, and every time Congress closes a loophole, it seems that three new ones take its place. Here, 75 years of tax history and tax evasion.

--Brian O'Keefe

Revenue Act of 1926 Reduces taxes--too much money being collected.

Revenue Act of 1932 Reaction to the Crash; prohibits deduction of short-term losses.

1934 Gregory case Businesswoman saves big through corporate reorganization. Judge Learned Hand finds no "patriotic duty to increase one's taxes" but rules against her.

1935 Supreme Court affirms Hand's decision.

1941-45 World War II War effort drives taxes up. Top rate reaches 94%.

Revenue Act of 1943 Introduces system of withholding on estimated taxes.

Late 1940s Collapsible-corporation schemes let Hollywood big shots direct more money into their own pockets.

Revenue Act of 1950 Stamps out collapsible corporations.

1951 Special provision written into tax code allows Louis B. Mayer to avoid paying tax on lump-sum retirement package.

Internal Revenue Code of 1954 Most monumental overhaul of tax system to date, makes 3,000 changes to rules.

1960 Knetsch case Taxpayer scheme to benefit from sham life insurance deal is squashed by Supreme Court. Strategy borrowed by corporate America in 1993, when Winn-Dixie supermarket chain tries to save $2 billion; Tax Court finds against it in 1999.

1963 John Kennedy champions tax cut--drops top rate from 91% to 70%.

1966 Tillie Goldstein case Courts deny shelter for elderly housewife on her Irish Sweepstakes lottery jackpot.

1969 Tax Court created as independent forum to mediate taxpayer disputes with IRS.

Tax Reform Act of 1969 Introduces the Minimum Tax.

Tax Reform Act of 1976 Attempt to eliminate tax shelters--targets limited partnerships.

Late 1970s Tax shelter mania in America--farming allowances lead taxpayers to start investing in Arabian horses, mink, and chinchillas.

1981 Reaganomics! Largest tax cut in history.

Reagan Tax Reform Act of 1984 Targets executive perks, requires more than 180 technical corrections.

1986 Gucci scion and chief designer Aldo Gucci pleads guilty to tax fraud.

Tax Reform Act of 1986 Cuts tax rates, broadens the tax base, and eliminates many loopholes that enabled shelters--ending boom era of personal tax shelters.

1989 Colgate saves itself $100 million in a Bermuda-based partnership with a Dutch bank--Supreme Court finds against them in 1997.

1997 Taxpayer Relief Act

2000 Treasury Secretary Lawrence Summers identifies corporate tax shelters as IRS Enemy No. 1, announces new Office of Tax Shelter Analysis.

Boss Hogs IRS cracks down on greedy corporate BOSS (Bond and Option Sales Strategy) schemes and individually tailored Son of Boss evasion plans.

SOURCES: IRS; DEPT. OF COMMERCE; U.S. BUDGET; CCH INC.; U.S. INCOME TAX, BY MICHAEL GRATZ; BROOKINGS INST.