Republican Iowa Sen. Chuck Grassley , the chairman of the SenateJudiciary Committee, is questioning whether Hillary Clinton paidlegal and public relations expenses for a former State Departmentaide and a tech company that worked on her private emailsystem.

“As you are aware, such arrangements can poseconflict-of-interest issues,” Grassley wrotein a letter he senton Tuesday to attorneys representing Clinton andseveral of her State Department aides, including Bryan Pagliano,the IT staffer who managed Clinton’s email system while shewas secretary of state.

Grassley appears concerned that Clinton’s former aides andthe tech companies she has hired to manage her mysterious emailsystem would continue to work on her behalf rather than provideinformation on the email arrangement to investigators.

“It is important for the Committee to know whetherSecretary Clinton and her attorneys are providing financialsupport, legal support, or other coordination to those associatesof hers who are involved in congressional committee and federal lawenforcement inquiries relating to her email server,” Grassleywrote.

He pointed specifically to a Sept. 16 invoice allegedly sent from PlatteRiver Networks, the Denver-based firm that began managingClinton’s server in June 2013, to Clinton’s accountant,Marcum, LLP.

Platte River Networks had housed Clinton’s server at a NewJersey data center but turned it over to the FBI in August afterthe Intelligence Community’s inspector general found that two“top secret” emails had been maintained on thedevice.

Hillary Clinton, (center), attends a party with former State Department staffer Bryan Pagliano, (right). (Facebook)

Hillary Clinton, (center), attends aparty with former State Department staffer Bryan Pagliano, (right).(Facebook)

The invoice, which was published last month by the websiteComplete Colorado, includes line items expensing legal work andpublic relations activities.

Under two entries for “Legal activity re: HillaryClinton,” Platte River Networks charged Marcum, LLP $2,720and $25,733 for the periods July 24 and July 31 and Aug. 3 to Aug.31, respectively. The invoice also includes a line itemfor $19,283 for “PR for Clinton email mediainquiries.”

The PR expenses were earmarked for a company called dovetailsolutions, another Denver-based company that Platte River Networkshired to manage its public relations as the Clinton email probeheated up this summer.

Andy Boian, the founder of dovetail solutions, did not returnThe Daily Caller’s request for comment about the invoice.

“The invoice raises questions as to whether SecretaryClinton has similar arrangements with other people or entitiesassociated with her email server,” Grassley wrote in theletter.

While Platte River Networks has claimed it is cooperating withthe FBI’s investigation, Politico reported earlier this month that the company hasrecently declined interview requests from FBI investigators andfrom the Senate Homeland Security Committee, which is alsoinvestigating Clinton’s server.

As Grassley noted in his letter, the Clinton campaign toldPolitico that “Clinton is not paying” outside firms fortheir legal and PR expenses related to the email probe. Politicoalso reported that the Clinton camp said that it had not receivedan invoice from Platte River Networks.

But as Grassley pointed out, the Clinton team’s statementthat it is “not paying” Platte River Networks waspresent tense. That leaves open the possibility that Clinton orMarcum, LLP paid for outside legal and PR services in the past.Grassley also noted that while the Clinton campaign deniedreceiving an invoice, it did not comment on whether her accountant,Marcum, LLP, had.

It would not be a surprise if Clinton and her team are issuingvague statements to conceal a financial arrangement with PlatteRiver Networks. Clinton has issued several lawyerly statementsabout her email account. One example is her initial claim that shedid not send or receive classified information on the emailaccount. But Clinton has since revised that statement, saying nowthat any classified information contained on the server was not“marked” classified when it was originated.

Grassley is also questioning whether Clinton has any financialarrangements with Pagliano, who pleaded the fifth during a briefinterview in September with the House Select Committee onBenghazi.

Grassley and the Senate Homeland Security Committee havediscussed whether to grant Pagliano immunity in order to testifyabout his work on Clinton’s email system.

“Given that the Committee has broached the idea ofimmunity with Mr. Pagliano, his involvement in a third-party feearrangement or joint defense agreement with any of the partiesabout whom he may be asked to testify would raise substantialconcerns,” Grassley wrote.

Pagliano worked as a staffer on Clinton’s 2008presidential campaign, and joined the State Department in May 2009,where he reportedly managed Clinton’s server. Clinton hassaid that Pagliano was not paid by the State Department for hiswork on the hardware and that she paid him from her personalfunds.

While Grassley did not name any specific conflicts of interestregarding Pagliano, he is being represented by Mark MacDougall, anattorney for Akin Gump, a Washington D.C. law firm that is one ofClinton’s biggest campaign donors. (RELATED: Law Firm Representing Hillary’s ITGuy Has Donated Heavily To Her Campaign)

As TheDC reported in September, five Akin Gump attorneys hadbundled nearly $130,000 in campaign contributions for Clintonthrough June 30.

Clinton’s campaign treasurer, Jose Villareal, is also asenior consultant at Akin Gump. And one of the firm’s seniorattorneys is Vernon Jordan, Jr., a longtime Clinton insider.

Akin Gump denied that the firm’s ties to Clinton hadanything to do with Pagliano hiring MacDougall. A spokesperson saidthat Pagliano was put in touch with the lawyer through a familyfriend who works at the firm.

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