New York Times: Big Tax Plans, Big Tax Risks:

Hardly anybody likes the current tax system. But as President Bush undertakes the potentially historic task of coming up with something better, he is confronting an issue that is more ideologically explosive, politically risky and economically complex than he let on during the campaign. In the days since his re-election, Mr. Bush has signaled that he is serious about following through, highlighting the topic in both his victory speech on Wednesday and his news conference on Thursday.

He has been vague about what he has in mind, but Republican advisers to the administration say the White House is debating whether Mr. Bush should back ambitious, even radical proposals like a national sales tax or a flat tax on income. By doing so, he would blast away a philosophy that has governed tax policy since Woodrow Wilson was in the White House: that higher levels of income should be taxed at higher rates.

New York Times: Taxes and Consequences: The Second Term Begins:

President Bush began his first term with projections for $5.6 trillion in budget surpluses. Though he will start his second term facing at least $2.3 trillion in deficits, according to the Congressional Budget Office, his tax-cutting ambitions are even greater. Here are some of the initiatives that he’s likely to push, and the unanswered questions that go with them:

• Privatization of Social Security
• Simplification of the Income Tax
• Making the 2001, 2002 and 2003 Tax Cuts Permanent
• Tax-Free Saving Accounts
• Abolishing the Tax on Dividends

New York Times: Lawsuit Over Tax Shelter May Derail a Settlement

A former director of America Online and a former senior AOL executive have sued the law firm of Jenkens & Gilchrist and two other entities, saying that they sold them aggressive tax shelters in 1999 and 2000 that were intended to shield $200 million in income from taxes but that were ruled invalid by the Internal Revenue Service. The lawsuit seeks at least $155 million and damages, and dims the prospects for a pending class-action settlement between Jenkens & Gilchrist and other wealthy investors who bought questionable tax shelters through the firm.

New York Times: A New York Tax Rule on Co-op-Sale Profits:

Under a New York State law passed this year, owners of co-op apartments in the state who are not state residents and who sell their apartments after Nov. 17 may have to pay tax on profits from the sale. And, if state taxes are due, the owners will be required to make an estimated tax payment within 15 days of the sale.

Wall Street Journal:  Bush Aims To Make Tax Cuts Permanent, Revamp Tax Laws:

Buoyed by a clear-cut election victory, President Bush is pledging to make permanent the sweeping tax cuts of his first term and to restructure the nation’s tax laws. The price tag on making the tax cuts permanent is more than $1 trillion, a daunting number in an age of record budget deficits. At the same time, efforts to enact ambitious proposals to overhaul the tax system often fall victim to a ferocious assault from Washington lobbyists determined to protect special breaks for their clients. While not discounting the challenges ahead, Bush’s supporters are betting that the president will end up getting much of what he wants with the help of bigger Republican majorities in both the House and the Senate.

Washington Post: How to Fix Taxes and Social Security:

With his reelection won, President Bush says he will move forward on two big domestic issues: the tax system and Social Security. Both are much in need of our attention; there was little serious discussion of either during the presidential campaign.

Washington Post: Giving a Car? Get It in Gear:

Thinking of donating your car or truck to charity? Hurry. At the end of the year, your tax-deductible coach turns into a pumpkin. After more than a year of listening to tales of abuse by taxpayers and charities alike, Congress last month changed the law on vehicle donations to make it much more difficult to get a big deduction for handing off your car or truck (or boat or airplane, if you have one of those) to a charity.

Washington Post: Consumption Tax