C.I.A. Secrets Could Surface in Swiss Nuclear Case


- By William J. Broad and David E. Sanger - December 23, 2010 - The New York Times

A seven-year effort by the Central Intelligence Agency to hide its relationship with a Swiss family who once acted as moles inside the world’s most successful atomic black market hit a turning point on Thursday when a Swiss magistrate recommended charging the men with trafficking in technology and information for making nuclear arms.

The prospect of a prosecution, and a public trial, threatens to expose some of the C.I.A.’s deepest secrets if defense lawyers try to protect their clients by revealing how they operated on the agency’s behalf. It could also tarnish what the Bush administration once hailed as a resounding victory in breaking up the nuclear arms network by laying bare how much of it remained intact.

“It’s like a puzzle,” Andreas Müller, the Swiss magistrate, said at a news conference in Bern on Thursday. “If you put the puzzle together you get the whole picture.”

The three men — Friedrich Tinner and his two sons, Urs and Marco — helped run the atomic smuggling ring of A. Q. Khan, an architect of Pakistan’s nuclear bomb program, officials in several countries have said. In return for millions of dollars, according to former Bush administration officials, the Tinners secretly worked for the C.I.A. as well, not only providing information about the Khan network’s manufacturing and sales efforts, which stretched from Iran to Libya to North Korea, but also helping the agency introduce flaws into the equipment sent to some of those countries.

The Bush administration went to extraordinary lengths to protect the men from prosecution, even persuading Swiss authorities to destroy equipment and information found on their computers and in their homes and businesses — actions that may now imperil efforts to prosecute them.

While it has been clear since 2008 that the Tinners acted as American spies, the announcement by the Swiss magistrate on Thursday, recommending their prosecution for nuclear smuggling, is a turning point in the investigation. A trial would bring to the fore a case that Pakistan has insisted is closed. Prosecuting the case could also expose in court a tale of C.I.A. break-ins in Switzerland, and of a still unexplained decision by the agency not to seize electronic copies of a number of nuclear bomb designs found on the computers of the Tinner family.

One of those blueprints came from an early Chinese atomic bomb; two more advanced designs were from Pakistan’s program, investigators from several countries have said.

Ultimately, copies of those blueprints were found around the globe on the computers of members of the Khan network, leading investigators to suspect that they made their way to Iran, North Korea and perhaps other countries. In 2003, atomic investigators found one of the atomic blueprints in Libya and brought it back to the United States for safekeeping.

Mr. Müller, the Swiss magistrate, investigated the Tinner case for nearly two years. He said Thursday that his 174-page report recommended that the three men face charges for “supporting the development of atomic weapons” in violation of Swiss law.

They are accused of supplying Dr. Khan’s operation with technology used to make centrifuges, the machines that purify uranium into fuel for bombs and reactors. Dr. Khan then sold the centrifuges to Libya, Iran and North Korea and perhaps other countries.

Mr. Müller’s recommendation comes as a new book describes previously unknown details of the C.I.A.’s secret relationship with the Tinners, which appears to have started around 2000.

The book, “Fallout,” by Catherine Collins and Douglas Frantz, scheduled to be published next month, tells how the C.I.A. sent the men coded instructions, spied on their family, tried to buy their silence and ultimately had the Bush administration press Switzerland to destroy evidence in an effort to keep the Tinners from being indicted and testifying in open court.

Ms. Collins is a freelance writer and investigator, and her husband, Mr. Frantz, is a former investigations editor for The New York Times and a former managing editor of The Los Angeles Times. He currently works on the staff of the Senate Foreign Relations Committee.

The C.I.A. has never commented on its relationship with the Tinners. But the story has leaked out, in bits and pieces, after news reports of Dr. Khan’s illicit atomic sales forced Pakistan’s government to expose the atomic ring and place Dr. Khan under house arrest. But Pakistan never allowed him to be interrogated by the C.I.A. or international nuclear inspectors, perhaps out of fear that he would implicate other Pakistani senior officials.

As a result, there has never been a full accounting of his activities, few of his associates have been tried or jailed, and there are strong indications that some of his suppliers are still operating.

But if the Pakistanis were worried about revelations surrounding Dr. Khan and whom he might have worked with in the Pakistani military and political hierarchy, the C.I.A. was worried about the Tinners.

The new book says the Bush administration grew so alarmed at possible disclosures of C.I.A. links to the family that in 2006 Secretary of State Condoleezza Rice lobbied Swiss officials to drop their investigation.

The book says the C.I.A. broke into a Tinner home in 2003 and found that the family possessed detailed blueprints for several types of nuclear bombs.

Paula Weiss, a spokeswoman for the C.I.A., declined to comment, and lawyers for the Tinners did not immediately respond to requests for comment. The Tinners have said that they were not aware that the equipment they supplied was intended for nuclear weapons projects.

Based on Swiss investigators’ findings, the book suggests that the bomb designs may have spread to a half dozen outposts of Dr. Khan’s empire around the globe — including Thailand, Malaysia and South Africa — and sharply criticizes the C.I.A. for leaving those plans in the hands of people suspected of being nuclear traffickers.

In late 2007, the Swiss government, under strong American pressure, decided to drop legal proceedings on espionage charges against the Tinners and other charges against a number of C.I.A. operatives who had operated on Swiss soil in violation of the country’s laws.

In early 2008, the more limited investigation on trafficking charges inched forward with great difficulty because the Swiss government — again at the behest of United States officials — had destroyed an enormous trove of computer files and other material documenting the business dealings of the atomic family. That action led to an uproar in the Swiss Parliament.

But in 2008 Swiss investigators discovered that 39 Tinner files scheduled for destruction had been overlooked, giving the authorities fresh insights into the ring’s operation — and new life for the legal case.

In his news conference on Thursday, Mr. Müller harshly criticized the Swiss government for having “massively interfered in the wheels of justice by destroying almost all the evidence.” He added that the government had also ordered the federal criminal police not to cooperate with his investigation.

If the Tinners are formally charged and their case goes to trial in Switzerland, they face up to 10 years in prison if they are found guilty of breaking laws on the export of atomic goods. All three men spent time in Swiss jails pending the outcome of the espionage and trafficking inquiries. The time they have already spent in jail would count toward any possible sentence.

In early 2009, Marco Tinner was freed after more than three years of investigative detention, and his brother Urs was released in late 2008 after more than four years in jail. Their father, Friedrich, was released in 2006.

Mr. Müller recommended that, in addition to charges of atomic smuggling, Marco Tinner should be accused of money laundering.

The Swiss attorney general is now studying the magistrate’s report and will decide next year whether to file charges against the Swiss family of atomic spies and entrepreneurs.


David Jolly contributed reporting from Paris.


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U.S. Enriches Companies Defying Its Policy on Iran


- By JO BECKER and RON NIXON - Published: March 6, 2010 - The New York Times

The federal government has awarded more than $107 billion in contract payments, grants and other benefits over the past decade to foreign and multinational American companies while they were doing business in Iran, despite Washington’s efforts to discourage investment there, records show.

That includes nearly $15 billion paid to companies that defied American sanctions law by making large investments that helped Iran develop its vast oil and gas reserves.

For years, the United States has been pressing other nations to join its efforts to squeeze the Iranian economy, in hopes of reining in Tehran’s nuclear ambitions. Now, with the nuclear standoff hardening and Iran rebuffing American diplomatic outreach, the Obama administration is trying to win a tough new round of United Nations sanctions.

But a New York Times analysis of federal records, company reports and other documents shows that both the Obama and Bush administrations have sent mixed messages to the corporate world when it comes to doing business in Iran, rewarding companies whose commercial interests conflict with American security goals.

Many of those companies are enmeshed in the most vital elements of Iran’s economy. More than two-thirds of the government money went to companies doing business in Iran’s energy industry — a huge source of revenue for the Iranian government and a stronghold of the increasingly powerful Islamic Revolutionary Guards Corps, a primary focus of the Obama administration’s proposed sanctions because it oversees Iran’s nuclear and missile programs.

Other companies are involved in auto manufacturing and distribution, another important sector of the Iranian economy with links to the Revolutionary Guards. One supplied container ship motors to IRISL, a government-owned shipping line that was subsequently blacklisted by the United States for concealing military cargo.

Beyond $102 billion in United States government contract payments since 2000 — to do everything from building military housing to providing platinum to the United States Mint — the companies and their subsidiaries have reaped a variety of benefits. They include nearly $4.5 billion in loans and loan guarantees from the Export-Import Bank, a federal agency that underwrites the export of American goods and services, and more than $500 million in grants for work that includes cancer research and the turning of agricultural byproducts into fuel.

In addition, oil and gas companies that have done business in Iran have over the years won lucrative drilling leases for close to 14 million acres of offshore and onshore federal land.

In recent months, a number of companies have decided to pull out of Iran, because of a combination of pressure by the United States and other Western governments, “terrorism free” divestment campaigns by shareholders and the difficulty of doing business with Iran’s government. And several oil and gas companies are holding off on new investment, waiting to see what shape new sanctions may assume.

The Obama administration points to that record, saying that it has successfully pressed allied governments and even reached out directly to corporate officials to dissuade investment in Iran, particularly in the energy industry. In addition, an American effort over many years to persuade banks to leave the country has isolated Iran from much of the international financial system, making it more difficult to do deals there.

“We are very aggressive, using a range of tools,” said Denis McDonough, chief of staff to the National Security Council.

The government can, and does, bar American companies from most types of trade with Iran, under a broad embargo that has been in place since the 1990s. But as The Times’s analysis illustrates, multiple administrations have struggled diplomatically, politically and practically to exert American authority over companies outside the embargo’s reach — foreign companies and the foreign subsidiaries of American ones.

Indeed, of the 74 companies The Times identified as doing business with both the United States government and Iran, 49 continue to do business there with no announced plans to leave.

One of the government’s most powerful tools, at least on paper, to influence the behavior of companies beyond the jurisdiction of the embargo is the Iran Sanctions Act, devised to punish foreign companies that invest more than $20 million in a given year to develop Iran’s oil and gas fields. But in the 14 years since the law was passed, the government has never enforced it, in part for fear of angering America’s allies.

That has given rise to situations like the one involving the South Korean engineering giant Daelim Industrial, which in 2007 won a $700 million contract to upgrade an Iranian oil refinery.

According to the Congressional Research Service, the deal appeared to violate the Iran Sanctions Act, meaning Daelim could have faced a range of punishments, including denial of federal contracts. That is because the law covers not only direct investments, such as the purchase of shares and deals that yield royalties, but also contracts similar to Daelim’s to manage oil and gas development projects.

But in 2009 the United States Army awarded the company a $111 million contract to build housing in a military base in South Korea. Just months later, Daelim, which disputes that its contracts violated the letter of the law, announced a new $600 million deal to help develop the South Pars gas field in Iran.

Now, though, frustration over Iran’s intransigence has spawned a growing, if still piecemeal, movement to more effectively use the power of the government purse to turn companies away from investing there.

Nineteen states — including New York, California and Florida — have rules that bar or discourage their pension funds from investing in companies that do certain types of business in Iran. Congress is considering legislation that would have the federal government follow suit, by mandating that companies that invest in Iran’s energy industry be denied federal contracts. The provision is modeled on an existing law dealing with war-torn Sudan.

Obama administration officials, while indicating that they were open to the idea, called it only one variable in a complex equation. Right now, the president’s priority is on breaking down Chinese resistance to the new United Nations sanctions, which apply across borders and are aimed squarely at entities that support Iran’s nuclear program.



But Representative Ron Klein, a Florida Democrat who wrote the contracting provision moving through Congress with the help of a lobbying group called United Against Nuclear Iran, said it offered a way forward with or without international agreement.

“We need to send a strong message to corporations that we’re not going to continue to allow them to economically enable the Iranian government to continue to do what they have been doing,” Mr. Klein said.

An Unused Tool

Sending a strong message was Congress’s intention when it passed the Iran Sanctions Act in 1996.

The law gives the president a menu of possible punishments he can choose to levy against offending companies. Not only do they risk losing federal contracts, but they can also be prevented from receiving Export-Import Bank loans, obtaining American bank loans over $10 million in a given year, exporting their goods to the United States, purchasing licensed American military technology and, in the case of financial firms, serving as a primary dealer in United States government bonds or as a repository for government funds.

Congress is now considering expanding its purview to a broader array of energy-related activities, including selling gasoline to Iran, which despite its vast oil and gas reserves has antiquated refineries that leave it heavily dependent on imports.

From the beginning, though, the law proved difficult to enforce.

European allies howled that it constituted an improper attempt to apply American law in other countries. Exercising an option to waive the law in the name of national security, the Clinton administration in 1998 declined to penalize the first violator — a consortium led by the French oil company TotalFina, now known as Total.

The administration also indicated that it would waive future penalties against European companies, winning in return tougher European export controls on technology that Iran could convert to military use.

Stuart E. Eizenstat, who as the deputy Treasury secretary handled those negotiations, said the law let Iran “exploit divisions between the U.S. and our European allies.”

Waiving it, though, was followed by additional investments in Iran — and more government largesse for the companies making them.

In 1999, for instance, Royal Dutch Shell signed an $800 million deal to develop two Iranian oil fields. Since then, Shell has won federal contract payments and grants totaling more than $11 billion, mostly for providing fuel to the American military, as well as $200 million in Export-Import loan guarantee and drilling rights to federal lands, records show.

Shell has a second Iranian development deal pending, but officials say they are awaiting the results of a feasibility study. In the meantime, the company continues to receive payments from Iran for its 1999 investment and sells gasoline and lubricants there.

Records show Shell is one of seven companies that challenged the Iran Sanctions Act and received federal benefits.

John R. Bolton, who dealt with Iran as an under secretary of state and United Nations ambassador in the Bush administration, said failing to enforce the law by punishing such companies both sent “a signal to the Iranians that we’re not serious” and undercut Washington’s credibility when it did threaten action.

Mr. Bolton recalled what happened in 2004 when he suggested to the Japanese ambassador that Japan’s state-controlled oil exploration company, Inpex, might be penalized for a $2 billion investment in the Azadegan field in Iran. “The Japanese ambassador said, ‘Well, that’s interesting. How come you’ve never sanctioned a European Union company?’ ” Mr. Bolton recounted.

Inpex was never penalized, though several years later it decided to reduce its stake in the Iranian project. And to Mr. Bolton’s chagrin, the Bush administration did not act on reports about other such investments, neither waiving the law nor penalizing violators.

Recently, after 50 lawmakers from both parties complained to President Obama about the lack of enforcement and sent him a list of companies that apparently violated the law, the State Department announced a preliminary investigation. Officials said that they were looking at 27 deals, and that while some appeared to have been “carefully constructed” to get around the letter of the law, they had identified a number of problematic cases and were focusing on companies still active in Iran.

Competing Interests

Among the companies on the list Congress sent to the State Department is the Brazilian state-controlled energy conglomerate Petrobras, which last year received a $2 billion Export-Import Bank loan to develop an oil reserve off the coast of Rio de Janeiro. The loan offers a case study in the competing interests officials must confront when it comes to the Iran Sanctions Act.

Despite repeated American entreaties, Petrobras had previously invested $100 million to explore Iran’s offshore oil prospects in the Persian Gulf.



But the Export-Import Bank loan could help create American jobs, since Petrobras would use the money to buy goods and services from American companies. Perhaps more important, it could help develop a source of oil outside the Middle East.

After The Times inquired about the loan, bank officials said that they asked for and received a letter of assurance from Petrobras that it had finished its work in Iran. A senior White House official, in a Nov. 13 e-mail message, said that while it was the administration’s policy to warn companies against such investments, “Brazil is an important U.S. trading partner and our discussions with them are ongoing.”

But if the administration hoped that the loan would bring Brazil in line with its objectives in Iran, it would soon prove mistaken.

On Nov. 23, Iran’s president, Mahmoud Ahmadinejad, visited Brazil, and the two countries agreed to share technical expertise on energy projects. Iranian officials said they might offer Petrobras additional incentives for further investment.

The visit infuriated American officials, who felt it undercut efforts to press Iran on its nuclear program while lending international legitimacy to the Iranian president. Brazil’s relationship with Iran has also complicated American maneuvering at the United Nations, where Brazil holds a rotating seat on the Security Council. Just last week, Brazil’s president, Luiz Inácio Lula da Silva, restated his opposition to the administration’s sanctions proposal, warning, “It is not prudent to push Iran against a wall.”

Carter Lawson, the Export-Import Bank’s deputy general counsel, acknowledged that Mr. Ahmadinejad’s visit was “problematic for us, and it raised our antenna.” He said that since December the bank had been operating under a new budget rule requiring borrowers to certify that they had no continuing operations in Iran’s energy industry, and was carefully monitoring Petrobras’s activities.

In the meantime, Petrobras’s Tehran office remains open. And Diogo Almeida, the acting economic attaché at the Brazilian Embassy in Iran, said that while Petrobras was currently assessing how much it could invest in Iran, given the huge discovery off Rio de Janeiro, company officials were in active discussions with the Iranian government and were interested in pursuing new business.

Opportunities for Profit

For all the American rules and focus, there is still plenty of room for companies to profit in crucial areas of Iran’s economy without fear of reprisal or loss of United States government business.

Auto companies doing business in Iran, for instance, received $7.3 billion in federal contracts over the past 10 years. Among them was Mazda, whose cars in Iran are assembled by a company called the Bahman Group. A 45 percent share in Bahman is held by the Sepah Cooperative Foundation, a large investment fund linked to the Revolutionary Guards, according to Iranian news accounts and a 2009 RAND Corporation report prepared for the Defense Department.

A Mazda spokesman declined to comment, saying the company was unaware of the links.

Even companies based in the United States, including some of the biggest federal contractors, can invest in Iran through foreign subsidiaries run independently by non-Americans.

Honeywell, the aviation and aerospace company, has received nearly $13 billion in federal contracts since 2005. That year it acquired Universal Oil Products, whose British subsidiary is working on a project to expand gasoline production at the Arak refinery in Iran. Universal recently received a $25 million federal grant for a clean-energy project in Hawaii.

In a statement, Honeywell said it had told the State Department in January that while it was fulfilling its Arak contract, it would not undertake new projects in Iran.

Ingersoll Rand, another American company with foreign subsidiaries, says it is evaluating its “minor” business in Iran in light of the political climate. But for now, according to a spokesman, Paul Dickard, it continues to sell air-compression systems with a “wide variety of applications,” including in the oil and gas industries and in nuclear power plants.

Senator Byron L. Dorgan, a North Dakota Democrat, tried to close the foreign subsidiary loophole after a furor erupted in 2004 over Halliburton, former Vice President Dick Cheney’s old company, which had used a Cayman Islands subsidiary to sell oil-field services to Iran. But he said he was unable to overcome business opposition.

William A. Reinsch, president of the National Foreign Trade Council, lobbied against Mr. Dorgan’s bill and has opposed other unilateral sanctions. He argues that their futility can be seen in the intransigence of the Iranian government and the way American oil companies have simply been replaced by foreign competitors. Moreover, many foreign companies with business interests in Iran are also large American employers; deny them federal contracts and other benefits, Mr. Reinsch said, “and it’s those workers who will pay the price.”

But Hans Sandberg, senior vice president of Atlas Copco, which is based in Sweden, offered a different perspective. Atlas Copco’s sales of mining and construction equipment to Iran are dwarfed by its American business, including military contracts. If forced to choose, he said: “It would be no problem. We wouldn’t trade with Iran.”

U.S. Approved Business With Blacklisted Nations


- By Jo Becker - December 23, 2010 - The New York Times

Despite sanctions and trade embargoes, over the past decade the United States government has allowed American companies to do billions of dollars in business with Iran and other countries blacklisted as state sponsors of terrorism, an examination by The New York Times has found.

At the behest of a host of companies — from Kraft Food and Pepsi to some of the nation’s largest banks — a little-known office of the Treasury Department has granted nearly 10,000 licenses for deals involving countries that have been cast into economic purgatory, beyond the reach of American business.

Most of the licenses were approved under a decade-old law mandating that agricultural and medical humanitarian aid be exempted from sanctions. But the law, pushed by the farm lobby and other industry groups, was written so broadly that allowable humanitarian aid has included cigarettes, Wrigley’s gum, Louisiana hot sauce, weight-loss remedies, body-building supplements and sports rehabilitation equipment sold to the institute that trains Iran’s Olympic athletes.

Hundreds of other licenses were approved because they passed a litmus test: They were deemed to serve American foreign policy goals. And many clearly do, among them deals to provide famine relief in North Korea or to improve Internet connections — and nurture democracy — in Iran. But the examination also found cases in which the foreign-policy benefits were considerably less clear.

In one instance, an American company was permitted to bid on a pipeline job that would have helped Iran sell natural gas to Europe, even though the United States opposes such projects. Several other American businesses were permitted to deal with foreign companies believed to be involved in terrorism or weapons proliferation. In one such case, involving equipment bought by a medical waste disposal plant in Hawaii, the government was preparing to deny the license until an influential politician intervened.

In an interview, the Obama administration’s point man on sanctions, Stuart A. Levey, said that focusing on the exceptions “misses the forest for the trees.” Indeed, the exceptions represent only a small counterweight to the overall force of America’s trade sanctions, which are among the toughest in the world. Now they are particularly focused on Iran, where on top of a broad embargo that prohibits most trade, the United States and its allies this year adopted a new round of sanctions that have effectively shut Iran off from much of the international financial system.

“No one can doubt that we are serious about this,” Mr. Levey said.

But as the administration tries to press Iran even harder to abandon its nuclear program — officials this week announced several new sanctions measures — some diplomats and foreign affairs experts worry that by allowing the sale of even small-ticket items with no military application, the United States muddies its moral and diplomatic authority.

“It’s not a bad thing to grant exceptions if it represents a conscious policy decision to give countries an incentive,” said Stuart Eizenstat, who oversaw sanctions policy for the Clinton administration when the humanitarian-aid law was passed. “But when you create loopholes like this that you can drive a Mack truck through, you are giving countries something for nothing, and they just laugh in their teeth. I think there have been abuses.”

What’s more, in countries like Iran where elements of the government have assumed control over large portions of the economy, it is increasingly difficult to separate exceptions that help the people from those that enrich the state. Indeed, records show that the United States has approved the sale of luxury food items to chain stores owned by blacklisted banks, despite requirements that potential purchasers be scrutinized for just such connections.

Enforcement of America’s sanctions rests with Treasury’s Office of Foreign Assets Control, which can make exceptions with guidance from the State Department. The Treasury office resisted disclosing information about the licenses, but after The Times filed a federal Freedom of Information lawsuit, the government agreed to turn over a list of companies granted exceptions and, in a little more than 100 cases, underlying files explaining the nature and details of the deals. The process took three years, and the government heavily redacted many documents, saying they contained trade secrets and personal information. Still, the files offer a snapshot — albeit a piecemeal one — of a system that at times appears out of sync with its own licensing policies and America’s goals abroad.

In some cases, licensing rules failed to keep pace with changing diplomatic circumstances. For instance, American companies were able to import cheap blouses and raw material for steel from North Korea because restrictions loosened when that government promised to renounce its nuclear weapons program and were not recalibrated after the agreement fell apart.

Mr. Levey, a Treasury under secretary who held the same job in the Bush administration, pointed out that the United States did far less business with Iran than did China or Europe; in the first quarter of this year, 0.02 percent of American exports went to Iran. And while it is “a fair policy question” to ask whether Congress’s definition of humanitarian aid is overly broad, he said, the exception has helped the United States argue that it opposes Iran’s government, not its people. That, in turn, has helped build international support for the tightly focused financial sanctions.

Beyond that, he and the licensing office’s director, Adam Szubin, said the agency’s other, case-by-case, determinations often reflected a desire to balance sanctions policy against the realities of the business world, where companies may unwittingly find themselves in transactions involving blacklisted entities.

“I haven’t seen any licenses that I thought we should have done differently,” Mr. Szubin said.

Behind a 2000 Law

For all the speechifying about humanitarian aid that attended its passage, the 2000 law allowing agricultural and medical exceptions to sanctions was ultimately the product of economic stress and political pressure. American farmers, facing sharp declines in commodity prices and exports, hoped to offset their losses with sales to blacklisted countries.

The law defined allowable agricultural exports as any product on a list maintained by the Agriculture Department, which went beyond traditional humanitarian aid like seed and grain and included products like beer, soda, utility poles and more loosely defined categories of “food commodities” and “food additives.”

Even before the law’s final passage, companies and their lobbyists inundated the licensing office with claims that their products fit the bill.

Take, for instance, chewing gum, sold in a number of blacklisted countries by Mars Inc., which owns Wrigley’s. “We debated that one for a month. Was it food? Did it have nutritional value? We concluded it did,” Hal Eren, a former senior sanctions adviser at the licensing office, recalled before pausing and conceding, “We were probably rolled on that issue by outside forces.”

While Cuba was the primary focus of the initial legislative push, Iran, with its relative wealth and large population, was also a promising prospect. American exports, virtually nonexistent before the law’s passage, have totaled more than $1.7 billion since.

In response to questions for this article, companies argued that they were operating in full accordance with American law.

Henry Lapidos, export manager for the American Pop Corn Company, acknowledged that calling the Jolly Time popcorn he sold in Sudan and Iran a humanitarian good was “pushing the envelope,” though he did give it a try. “It depends on how you look at it — popcorn has fibers, which are helpful to the digestive system,” he explained, before switching to a different tack. “What’s the harm?” he asked, adding that he didn’t think Iranian soldiers “would be taking microwavable popcorn” to war.

Even the sale of benign goods can benefit bad actors, though, which is why the licensing office and State Department are required to check the purchasers of humanitarian aid products for links to terrorism. But that does not always happen.

In its application to sell salt substitutes, marinades, food colorings and cake sprinkles in Iran, McCormick & Co. listed a number of chain stores that planned to buy its products. A quick check of the Web site of one store, Refah, revealed that its major investors were banks on an American blacklist. The government of Tehran owns Shahrvand, another store listed in the license. A third chain store, Ghods, draws many top officials from the Islamic Revolutionary Guards Corps, which the United States considers a terrorist organization.

The licensing office’s director, Mr. Szubin, said that given his limited resources, they were better spent on stopping weapons technology from reaching Iran. Even if the connections in the McCormick case had come to light, he said, he still might have had to approve the license: the law requires him to do so unless he can prove that the investors engaged in terrorist activities own more than half of a company.

“Are we checking end users? Yes,” he said. “But are we doing corporate due diligence on every Iranian importer? No.”

A McCormick spokesman, Jim Lynn, said, “We were not aware of the information you shared with us and are looking into it.”

Political Influence

Beyond the humanitarian umbrella, the agency has wide discretion to make case-by-case exceptions. Sometimes, political influence plays a role in those deliberations, as in a case involving Senator Daniel Inouye of Hawaii and a medical-waste disposal plant in Honolulu.

On July 28, 2003, the plant’s owner, Samuel Liu, ordered 200 graphite electrodes from a Chinese government-owned company, China Precision Machinery Import Export Corporation. In an interview, Mr. Liu said he had chosen the company because the electrodes available in the United States were harder to find and more expensive. Two days later, the Bush administration barred American citizens from doing business with the Chinese company, which had already been penalized repeatedly for providing missile technology to Pakistan and Iran.

By the time Customs seized the electrodes on Nov. 5, waste was piling up in the sun. Nor did prospects look good for Mr. Liu’s application to the licensing office seeking to do an end run around the sanctions. On Nov. 21, a State Department official, Ralph Palmiero, recommended that the agency deny the request since the sanctions explicitly mandated the “termination of existing contracts” like Mr. Liu’s.

That is when Senator Inouye’s office stepped in. While his electrodes were at sea, Mr. Liu had made his first ever political contribution, giving the senator’s campaign $2,000. Mr. Liu says the timing was coincidental, that he was simply feeling more politically inclined. Records show that an Inouye aide called the licensing office on Mr. Liu’s behalf the same day that Mr. Palmiero recommended denying the application. The senator himself wrote two days later.

Mr. Inouye’s spokesman, Peter Boylan, said the contribution had “no impact whatsoever” on the senator’s actions, which he said were motivated solely by concern for the community’s health and welfare.

The pressure appears to have worked. The following day, the licensing office’s director at the time asked the State Department to reconsider in an e-mail that prominently noted the senator’s interest. A few days later, the State Department found that the purchase qualified for a special “medical and humanitarian” exception.

The license was issued Dec. 10. Two months later, Mr. Liu sent the senator another $2,000 contribution, the maximum allowable. Mr. Levey said he could not comment on the details of a decision predating his tenure. But he noted that sanctions against the Chinese company had since been toughened, and added, “Certainly this transaction wouldn’t be authorized today.”

Curious Exemptions

Mr. Liu’s license is hardly the only one to raise questions about how the government determines that a license serves American foreign policy.

There is also, for instance, the case of Irisl, an Iranian government-owned shipping line that the United States blacklisted in 2008, charging that because it routinely used front companies and misleading terms to shroud shipments of banned arms and other technology with military uses, it was impossible to tell whether its shipments were “licit or illicit.”

Less than nine months earlier, the licensing office had permitted a Japanese subsidiary of Citibank to carry out the very type of transaction it was now warning against. Records show that the bank had agreed to confirm a letter of credit guaranteeing payment to a Malaysian exporter upon delivery of what were described as split-system air-conditioners to a Turkish importer. Though the government had yet to blacklist Irisl, sanctions rules already prohibited dealings with Iranian companies. So when the bank learned that the goods were to be shipped aboard the Irisl-owned Iran Ilam, it sought a license.

The license was granted, even though the Treasury Department’s investigation of Irisl was well under way and the United States had reason to be suspicious of the Iran Ilam in particular; that summer, the ship had attracted the attention of the intelligence community when it delivered a lathe used to make nuclear centrifuge parts from China to Iran, according to government officials who requested anonymity to speak about a previously unpublicized intelligence matter.

Mr. Szubin said that since the blacklisting of Irisl, his agency had forced banks to extricate themselves from such transactions. But at the time the Citibank license was issued, his agency regularly issued licenses in cases like this one, where at the time of the transaction, the bank had no way of knowing that Irisl was involved and where the shipping line would be paid by a foreign third party anyway. To depart from the norm, he said, risked facing a lawsuit charging unfair treatment and tipping Irisl off that it was under investigation.

But if the government has sometimes been willing to grant American businesses a break, some companies have recently decided that the cost to their reputations outweighs the potential profit.

General Electric, which has been one of the leading recipients of licenses, says it has stopped all but humanitarian business in countries listed as sponsors of terrorism and has promised to donate its profits from Iran to charity.

As Joshua Kamens, the head of a company called Anndorll, put it, he knew from almost the minute he applied for a license to sell sugar in Iran that “it would come back to haunt me.” Although he received the go-ahead, he decided to back out of the deal.

“I’m an American,” he said. “Even though it’s legal to sell that type of product, I didn’t want to have any trade with a country like Iran.”


Ron Nixon contributed reporting from Washington, and William Yong from Tehran.