Detroit officials repeatedly mischaracterized the true nature of city fundraising efforts on behalf of a nonprofit run by a woman with close ties to Mayor Mike Duggan, newly-released documents reveal.

Ever since an initial Free Press investigation revealed city fundraising and grant support for the Make Your Date nonprofit in April, administration officials have downplayed fundraising by the city, saying they were limited to only a few initial attempts before withdrawing and allowing others to take over the effort.

But documents originally requested by the newspaper months ago under a Freedom of Information Act request show staffers from the city development office were engaged in meetings and correspondence with potential donors as late as November 2018 — several years into the operation of the nonprofit.

The City of Detroit released 211 pages of deleted emails Friday. The emails were mysteriously deleted during the Free Press' investigation into the city's support for the Make Your Date program, during which city officials claimed that the city's fundraising efforts were brief.

When the Free Press questioned city officials last month about the deleted emails, the city's top lawyer announced that they would be recovered and released to the public. Who was behind deleting the emails remains unknown.

The Michigan Attorney General's office opened an investigation into the deleted emails in recent days, a spokeswoman confirmed on Friday. The office previously classified its look into the deleted emails as a "review." Destroying public records is a crime punishable by up to two years in prison.

"It has moved to investigation status and a criminal prosecutor has been assigned to the case," said spokeswoman Kelly Rossman-McKinney.

The recovered emails contradict previous claims from Duggan's office that the city devoted scant resources toward raising money for the Make Your Date program, a prenatal program run by Dr. Sonia Hassan, who Duggan was seen visiting after hours last summer at a suburban residence.

The emails show at least two city workers were integral in the fundraising. Hassan personally thanked one of them in June 2018.

"I wanted to drop you a line and thank you so much for all your efforts with us. You bring great knowledge and energy to the table for this process. It is greatly appreciated," Hassan wrote to Monique Phillips, a development officer for the city.

Phillips was central to the city's fundraising efforts, the emails show. At one point, she coached Make Your Date leaders on how to ask for money. Phillips suggested they emphasize Duggan's support for their program in a March 2018 email that sought funding from the Skillman Foundation.

Phillips declined comment.

Phillips identified potential donors for Make Your Date, attended donor meetings, submitted funding proposals and updated Make Your Date staff members on their progress, the emails show.

Phillips transferred her duties with Make Your Date to another city development officer, Claire Huttenlocher, in June 2018, the emails show.

A Make Your Date spreadsheet was attached to some of the emails. But the spreadsheet, along with other email attachments, was not included in the city's public release of the emails in a posting on the Detroit law department's website.

Beyond targeting specific donors, the emails show Make Your Date hoped to raise $2 million to serve up to 15,000 women and expand throughout the city and into schools and churches.

In a statement accompanying the recovered emails, Lawrence Garcia, the city's top government attorney, said he believes all the deleted emails have been recovered and any deleted emails discovered in the future will be added to the law department's posting.

"The emails come from dates in late 2017 and 2018. They are electronic correspondence belonging to two junior staff members of the Detroit Office of Development and Grants (ODG) concerning their work with Wayne State University (WSU) to identify charitable contributions for WSU's Make Your Date program — an effort that has helped thousands of pregnant women and babies," Garcia said in the statement. "Reducing infant mortality has been a long-standing priority for Detroit, and Make Your Date's mission aligns with the City's goal of helping expectant mothers."

The Detroit Office of the Inspector General also is investigating the circumstances surrounding the deleted emails and Garcia said he would not comment further until the investigation is complete.

The emails show the city's fundraising campaign involved several more potential donors to Make Your Date than Duggan's office previously specified to the Free Press during its investigation into the city's support for the program.

Duggan's office said in April that the city's fundraising effort for Make Your Date only involved "preliminary inquiries" and concept papers to the Skillman Foundation and the Children's Hospital of Michigan Foundation, and that zero dollars were actually raised. The mayor's office has repeatedly claimed that Make Your Date is a Wayne State University program.

"City staff briefly collaborated with the Wayne State philanthropy department to try to raise funds for the Wayne State program, but those efforts were unsuccessful and no funds were raised," Alexis Wiley, Duggan's chief of staff, wrote to the Free Press in an April 2 email. "At no time did anyone from the city participate in any fundraising effort for a Make Your Date nonprofit -- all efforts were a direct collaboration with the university staff for the university-run program."

But the emails released Friday show that the city was involved in courting donations from the Ford Foundation, Fiat Chrysler, Blue Cross Blue Shield of Michigan, The Kresge Foundation, the Robert Wood Johnson Foundation, the Sean Anderson Foundation, the Michigan Health Endowment Fund, the W.K. Kellogg Foundation, March of Dimes, The Carl's Foundation and an organization listed as the "Fisher Foundation." And those communications cite a nonprofit organization, not a university program, as do other fundraising materials that note 501(c)(3) status of Make Your Date.

The Carl's Foundation gave Make Your Date a $51,285 grant in October 2018.

The Free Press submitted a Freedom of Information Act request for emails related to the city's work with Make Your Date in May. The city required $881 for the emails and the Free Press paid a deposit in June but has not yet received the records.

A former city official told the Free Press in July that two workers in the Detroit Office of Development and Grants, who conducted fundraising for Make Your Date, were instructed to delete their emails to conceal the extent of the city's support for the maternal health program.

Kennedy Shannon, the former assistant director of the Development and Grants Office, said in an interview that Phillips approached her in April to talk about the deleted emails, days after publication of the Free Press’ investigation into Make Your Date and Duggan’s ties to Hassan.

Shannon worked alongside the employees and described in written complaints to the Detroit Inspector General and the Attorney General’s office how her co-workers were told to delete their Make Your Date emails.

“I definitely think it’s a cover-up," Shannon told the Free Press in an interview. "And I think it’s an attempt to hide the fact that more city resources were spent ... than what the mayor said they were.”

The deleted emails were later recovered once administration officials reversed the order, Shannon said.

Both the Attorney General’s Office and Detroit’s Office of Inspector General previously launched inquiries into Make Your Date after the Free Pressrevealed that the city provided the program with $358,000 in federal grants and that Duggan ordered the fundraising campaign, which included the city's highest ranking development officer, back in 2017.

Attorney General Dana Nessel instructed her criminal division last month to look into the allegations of deleted emails after the issue was brought to her attention.

Nessel personally weighed in after her criminal division chief initially deferred the deleted email complaints to the Detroit Inspector General.

Shannon said it was an FOIA request earlier this year, around February, that preceded the order to delete emails.

Once details of Duggan’s relationship with Hassan and the city’s support for Make Your Date were published by the Free Press in April, Shannon said Phillips became upset about having followed orders months earlier to delete her emails.

Garcia said last month Mayor Duggan and Detroit Chief Financial Officer Dave Massaron learned in May about the possibility some emails related to Make Your Date had been deleted.

"CFO Massaron promptly took the lead in the effort to recover the emails. To the best of our knowledge, the deleted emails were successfully retrieved," Garcia said. "Approximately two months ago, the Office of Inspector General was informed of the circumstances and was provided the emails recovered."

It took several attempts by the Free Press to obtain emails during its initial April investigation because city officials said emails showing that Duggan had ordered fundraising efforts for Make Your Date had been "corrupted."

Messages from city officials to Hassan were not included in the city’s initial 395-page response to a Freedom of Information Act request, which had been reviewed by the law department.

Instead, the initial FOIA response included a single email between Wiley, Hassan and the city’s chief development official, Ryan Friedrichs, with a message body that read, “Attachment is corrupted.” After the Free Press questioned the "corrupted" notation on the attachment, the city provided the emails about the fundraising campaign and explained that “clean copies” were eventually discovered during a “manual search.”

As the OIG began looking into Shannon’s claims about the deleted emails, the Free Press put in a public records request for emails related to Make Your Date that were sent and received by employees who were ordered to delete them.

The day after the FOIA request for those emails, Friedrichs called a meeting with those employees to discuss the prior directive to delete the messages, Shannon said.

At the meeting, Friedrichs apologized and said the emails would be recovered.