Osama El-Atari, a restaurateur known for his flashy style and expensive sports cars, was sentenced to two days in the Loudoun County jail for driving on a suspended license.

But El-Atari never served the two days. He was booked into the Adult Detention Center in Leesburg at 7 a.m. on May 22, 2007. And by 8:13 a.m., he was a free man, according to law enforcement records obtained by The Washington Post.

The previous day, Loudoun County Sheriff Stephen O. Simpson’s reelection campaign deposited a $5,000 check from the Original Steakhouse, an Ashburn restaurant owned by El-Atari, according to campaign finance records.

Simpson, the chief law enforcement officer in Loudoun, a booming county of about 300,000 people, said he had nothing to do with El-Atari’s release. Such releases, he said, are fairly common for nonviolent offenders when jails are crowded.

But as Simpson seeks his fifth term this year, the El-Atari donation and several others from people and businesses that rely on county contracts have raised questions among Simpson’s critics and county leaders about whether the intersection of politics and policing is resulting in potential conflicts.

Some of his donations came from companies that do business directly with his agency and that have policies against political contributions, records and interviews show. None of the companies contributed money to any member of the elected county Board of Supervisors, according to records compiled by the Virginia Public Access Project.

Simpson (I) is unique in the immediate Washington area in that he is an elected top law enforcement officer. Fairfax, Prince William and Arlington counties and Alexandria in Virginia; the District; and Montgomery and Prince George’s counties in Maryland have police chiefs appointed by mayors, county executives or boards of supervisors. The chiefs devote their full attention to overseeing law enforcement, without the distraction of campaign fundraising and running for office.

Loudoun officials previously have discussed moving away from a sheriff’s department as the county’s top law enforcement agency, but the subject has never received even lukewarm support. Board of Supervisors Chairman Scott K. York (I-At Large) said he remains convinced that Loudoun should “seriously examine” whether to establish a county-wide police force.

“York has said it’s time to take the politics out of law enforcement. That’s ridiculous,” Simpson said. “If you take out someone who is elected by and accountable to the citizens and instead have someone appointed by nine elected officials, each with their own political agenda, that certainly doesn’t take the politics out of law enforcement at all. It makes it worse.”

El-Atari once was well known as one of Simpson’s most generous political benefactors. Campaign finance records show that he donated $20,000 to Simpson’s 2007 reelection campaign — about 20 percent of the total raised by Simpson that year.

But all that ended last August, when El-Atari was sentenced to 12 years in federal prison for fraudulently obtaining more than $71 million in loans from banks in Virginia, Maryland, Tennessee and Ohio.

After the sentencing, Simpson came under public pressure to return a $15,000 donation made by El-Atari in 2008, months after Simpson won reelection.

Simpson was initially reluctant to return the funds but decided to give the money to charity, making 15 donations of $1,000 each to local nonprofit organizations in December.

The sheriff said he took the donations from El-Atari in good faith and felt “betrayed” when he later learned of El-Atari’s crimes. He said he was not in a position to grant favors to El-Atari despite El Atari’s occasional bragging about the influence of his donations.

“I can’t let people go early. I can’t keep people longer,” said Simpson, whose office oversees the county jail through a direct chain of command. “Whether [El-Atari] thought it would help, I have no idea. That’s not a discussion we ever even had. . . . He ran his mouth to that effect, but that’s his lifestyle. That’s what got him in trouble — living larger than he really was.”

Beyond Loudoun, there is a long history of concern about the overlap of politics and law enforcement, said Dennis Kenney, an expert in police management and professor at the John Jay College of Criminal Justice.

“The police, if they stand for election, are far too easy to influence — not by voters specifically, but by folks who are able to either rally large blocks of voters or donate large amounts of money,” Kenney said.

VRT and Conmed

Simpson, who has served as Loudoun’s sheriff since 1995, also has received more than $3,500 in donations from Virginia Regional Transit — a nonprofit organization barred from making contributions to political candidates.

VRT receives about $1 million a year from Loudoun to help operate buses and trains, said county Treasurer H. Roger Zurn Jr., who spotted a $1,480 donation from the transit company on Simpson’s July 2010 campaign finance report.

Simpson returned those funds last August, and county auditors went through VRT’s records and found no other donations for fiscal 2010, Zurn said.

But “later on, I found out that it wasn’t their only donation,” Zurn said.

Mark McGregor, chief executive of VRT, told the Board of Supervisors in February that the donation was a mistake. He thought the check was written to support a charity golf tournament, not Simpson’s reelection.

McGregor acknowledged that he had made personal contributions to Simpson’s campaign and told the board that “the agency does not make political donations.”

But county records show the check from VRT was made out to Simpson’s reelection campaign, Zurn said, and Simpson’s campaign finance reports show a series of regular donations from VRT dating to 2006 that total more than $3,500.

In an interview, McGregor said he was unaware of the previous contributions.

“It was not our intent to make a political donation, nor was it [Simpson’s] intent to pursue a political donation from a not-for-profit,” he said. “The only thing we ever did with Steve was do golf tournaments. . . . We’ve never knowingly given to any of his political campaigns.”

Simpson said he was unaware that the organization was forbidden from making political donations: “I had no information regarding their tax status.”

The sheriff also has received donations from a company that does business with the department he oversees.

Conmed Healthcare Management provides inmate health services at the county jail. The company first donated $360 to Simpson within weeks of its winning its first contract, for $1.1 million, with the county in 2005.

Conmed increased its contribution to $2,940 in 2008, a year after the county renewed the contract for $1.9 million.

When Conmed’s contract came up again in 2009, Simpson wrote a letter to the Board of Supervisors, urging approval of the two-year, $2.4 million renewal. Two days after the county finance committee recommended that the board renew the contract, a $2,500 donation from the company was deposited in Simpson’s campaign account.

Simpson received another $2,500 donation from Conmed on May 10, according to a campaign finance report filed last month.

The company’s code of conduct appears to prohibit political donations, stating that Conmed is not permitted to contribute “money, property, time, or services (directly or indirectly) to any political candidate or political party.”

Conmed did not respond to requests for comment.

Simpson said that despite his office’s oversight of the Adult Detention Center, he is not involved in assessing the performance of companies contracted to do work at the jail and did not recall writing a letter in support of Conmed’s contract renewal in 2009.

“It’s probably something [jail officials] wrote for my signature,” he said.

Conmed wasn’t the only company that provided services to the Adult Detention Center and donated funds to Simpson’s campaign, according to county records. Two companies with jail-related phone and commissary contracts have donated to Simpson annually since 2006.

JK Moving Services

Other companies, such as JK Moving Services, a national business that owns a local fleet of more than 100 vehicles subject to inspection by local law enforcement, also have made regular donations to Simpson’s campaign.

JK Moving Services, which has a contract to provide moving and storage services to Loudoun, made a $1,000 donation to Simpson one day after its three-year, $350,000 contract with the county was approved.

Rebecca Chanin, a spokeswoman for JK Moving Services, said that the company won a competitive bid for the county contract and that the donations to Simpson do not pose a conflict of interest.

“We have a lot of employees, and we have a lot of valuable equipment around here,” she said. “We think he does a very good job of protecting us . . . so we continue to support him.”

It is neither illegal under Virginia law nor unusual for companies with county contracts to donate to politicians, a fact Simpson has emphasized. He said that the donations were timed in connection to an annual campaign fundraising golf tournament he hosts each spring and that any proximity to the execution of particular contracts was coincidental.

“It’s unrelated timing,” Simpson said. The county’s contractual relationship with the companies did not pose a conflict where contributions were concerned, he said.

“If you don’t go to the people you know, who do you go to?” he said.