One of the questionable money orders delivered to the Orange campaign, from JT Real Estate Holdings. (Orange At-Large)

In today’s Post, Nikita Stewart and I took a close look at businessman Jeffrey E. Thompson’s political donations in the city — particularly money order donations that went from his network to candidates including Mayor Vincent C. Gray (D) and D.C. Council member Vincent B. Orange (D-At Large).

As we explain, money orders can be an easy way to shield so-called “straw donations,” and campaign finance attorneys we spoke to generally advise their candidate-clients to steer clear of them, especially large ones. And Thompson wasn’t the only prominent city contractor we found to campaign money orders.

On March 10 of last year, four $1,000 money orders were donated to D.C. Council member Michael A. Brown (I-At Large), who was raising funds to close out his 2008 campaign account.

They came from four persons related to Emmanuel Bailey, who has been very much in the public eye due to the lottery contract saga. In a much analyzed and criticized move, Bailey was brought on late in the process by winning bidder Intralot to ease D.C. Council approval of its contract and — fairly or unfairly — has been the target of much scrutiny since.

In an interview, Bailey identified the four donors as his mother, brother, sister and girlfriend; Bailey himself gave a $1,000 check. Bailey’s mother had previously donated to several campaigns using checks; his sister also donated a $500 money order last June to Ward 4 Democrat Muriel Bowser’s re-election bid.

He said that March 2011 donations were in the form of money orders because he had solicited them when the five of them were together for a family occasion. His brother is “unbanked” does not have a checking account, he explained, and the other three didn’t have their checkbooks with them at the time.

Going to a bank together to purchase the money orders, he said, “was just the easiest thing to do.”

”I didn’t go round up people and round up money orders,” said. “We were just together that particular day. It was a matter of convenience.”

Six days later, Brown returned the four money orders, and he said Monday he no longer has them in his possession.

Brown declined to comment on why he returned them except to say that “well before these issues arose [with Thompson-related money orders], we on our own decided not to take any money orders anymore.”

So why didn’t those donors who had simply forgotten their checkbooks then write checks? “Quite frankly, no one asked me for any more money,” Bailey said.

Tomorrow, D.C. Council member Mary M. Cheh (D-Ward 3) will introduce legislation restricting money order donations to $25 — the same limit placed on cash contributions. “If you have $500 or $1,000, you probably have a checking account,” Cheh said, notwithstanding the financial situation of Bailey’s brother.

As of this evening, four colleagues had signed up as co-sponsors: Chairman Kwame R. Brown (D), Jack Evans (D-Ward 2), Orange and Michael Brown. Gray also said he supports Cheh’s bill in comments today to WTTG-TV’s Matt Ackland.

Bailey said he supports further campaign finance reform — specifically, barring city contractors like him from donating to political campaigns. “That would be a good scenario,” he said.

UPDATE, 8 A.M.: Bailey clarifies that his brother is not “unbanked.” He has a savings account, but not a checking account.