In an email to a New York City Department of Parks & Recreation staffer, FreshDirect executive Larry Scott Blackmon hinted that, as a former Parks Department employee, he was nearly free of a one-year ban on interacting with the agency.

“FYI - my ban is up… It’s on now!!!!!” Blackmon wrote in a July 13, 2015, email to Karina Smith, chief of staff for the department’s community outreach.

“I know that’s right!” Smith wrote back later that day.

It appears that it had been on for weeks, however. Emails obtained by City & State show Blackmon had already sent at least half a dozen emails to Smith about FreshDirect potentially sponsoring a July 25 event before he had been gone from the agency for a full 12 months.

The email exchange raises questions about whether he violated the city charter’s conflicts of interest law. A provision prevents city employees who join the private sector from appearing for one year before the agency where they worked. The measure defines “appear” as engaging in any communication for compensation, other than “ministerial” matters such as requesting a fax number.

Blackmon resigned from his Parks Department position as deputy commissioner for community outreach on July 17, 2014, according to the city. He started at FreshDirect a few days later, on July 21.

Before the one-year ban appears to have expired on July 17, 2015, the emails suggest Blackmon negotiated the details of FreshDirect’s $2,500 sponsorship of an event celebrating the reopening of the High Bridge, the oldest bridge in the city, which spans Washington Heights and the Bronx.

Parks Department personnel independently reached out to the city’s Conflicts of Interest Board to clarify potentially applicable conflict of interest rules and the matter is under review, according to the agency. An agency spokesperson stressed that it initiated the sponsorship discussion with Blackmon.

Blackmon did not respond to requests for comment.

On May 7, the email exchange shows Smith, the department’s community outreach chief of staff, wrote to Blackmon, “Great speaking with you today about this opportunity.” In the email, she noted that she was attaching a package outlining sponsorship levels for the High Bridge Festival.

About a month later, documents show Smith emailed Blackmon, writing, “Thanks so much for Fresh Direct’s $2500 Sponsorship Commitment for the Highbridge Fest!” Minutes later Blackmon replied, saying he was attaching logo images and asking if the event would be ticketed.

Soon, Smith was emailing Blackmon copies of a sponsorship agreement and asking him to return a signed version. Emails Smith exchanged with Parks Department colleagues indicate the department modified the agreement so that it was not addressed to Blackmon, but to FreshDirect’s Executive Vice President and General Counsel Mike Brizel, and that insurance requirements were removed because the online grocer did not plan on having a physical presence at the event. After Smith asked Blackmon if the contract was close to being approved, he wrote back July 9, “My counterpart in Legal is reviewing the contract. I will have the check by Monday. Let me know how you want to receive the check.” He then described the contract as “obese.”

By July 13, the parties appeared close to an agreement, with Smith noting that the Parks Department’s counsel had agreed to changes and that she would like FreshDirect to return the attached agreement with a signature and send a check. At that point, Blackmon responded that his colleague would “execute the contract” the following day, tacking on the note that his ban was up.

The Parks Department told City & State that FreshDirect was sent a contract, but it was not signed and returned. Still, the sponsorship moved forward. FreshDirect sent a check dated July 15, 2015, and, in exchange, had its logo displayed on promotional posters and postcards ahead of the event, according to the department. The department also said sponsorship agreements are more important when a sponsor is slated to be at an event doing sampling, giveaways or leading activities and liability insurance is needed. The city said it is rare but not unheard of for a sponsorship to occur without a signed agreement in place.

Blackmon, who worked on former Mayor Michael Bloomberg’s campaign and started at the Parks Department on Feb. 16, 2010, joined FreshDirect as the company embarked on a move from Queens to the Harlem River Yards. Some in the surrounding Port Morris area opposed the relocation, which is aided by government subsidies, because they feared the grocer’s trucks would exacerbate pollution and it would not create high-paying jobs. As a candidate, de Blasio criticized the arrangement. His administration has said that it “really tried” to halt the move, but could not alter a deal inked under Bloomberg.

Mychal Johnson, a member of a coalition opposing FreshDirect’s move called South Bronx Unite, said the group pressed the Parks Department not to let the grocer sponsor the event.

“We were definitely concerned with the fact that (Blackmon) was using his prior position and influence to advance his current agenda,” Johnson said. “His prior position at City Parks, for us, felt really symbolic of how things have been going for way too long.”

“FreshDirect was among a number of well-recognized companies that sponsored the event, albeit at modest $2,500 level,” a company spokesperson said in a statement. “We are grateful to the New York City Department of Parks and Recreation for the opportunity to be a sponsor and look forward to future opportunities to give back to the communities in which our customers live.”

 You can read the email exchange below:

FreshDirect Emails