Robin Miller, a racing analyst for the SPEED channel, said the end of May had to be "D-Day" for the Baltimore race.
Miller said he believed IndyCar would go to great lengths to ensure the race happens.
"If IndyCar has to be the promoter, there will be a Baltimore race," he said. "I can assure you that they will spend what they need to spend."
Last year's event was heralded by drivers and racing fans as one of the highlights of IndyCar's season. The race along a 2-mile stretch of roads near the Inner Harbor allowed IndyCar to expand its presence on the East Coast, Miller said. Organizers sold 110,000 tickets to the three-day event, which one study concluded generated $47 million in economic impact for the city.
But Baltimore Racing Development, the organizers of the 2011 race, collapsed financially soon after the event, failing to pay contractors and state agencies. After the group did not pay $1.5 million in taxes and fees to the city, Rawlings-Blake's administration canceled the group's contract in December.
City officials then entered into exclusive closed-door negotiations with the team behind Downforce — Dillon, who had worked on previous Indycar races, and Dawson and Reck, former Constellation Energy Group executives.
Both IndyCar executives and city officials sang Dillon's praises, particularly his work as the general manager of Baltimore Racing Development in the final weeks before last year's race.
City officials hammered out a contract with Downforce that they said would allow them to closely monitor the group's progress and head off the financial problems wrought by last year's group. The contract specified two sets of benchmarks for the race organizers — an initial round to be met by March 15 and a second May 1.
Downforce has failed to meet three of the five milestones that were due March 15. The group has not settled agreements with IndyCar or the Maryland Stadium Authority, nor has it completed a ticket escrow deal with the city.
At least two of the documents are nearly complete but lack a crucial element — Dillon's signature — city and state officials say. Officials inititally attributed the delay to a death in Dillon's wife's family, but later acknowledged that the documents were not signed because of internal strife at Downforce.
Maryland Stadium Authority executive director Mike Frenz said Monday that Dillon had yet to sign the agreement with his agency.
"It's pretty clear now that … Dale might be out of the picture," Frenz said.
By Tuesday, the city contract requires Downforce to finalize agreements with the Parking Authority, the Convention Center and the Maryland Transit Adminstration. The race group also is supposed to present a safety and security plan to the city by that date.
City officials declined to say when or if they would take action over the missed deadlines.
When asked if there were a cut-off date for plans for the race, Rawlings-Blake said, "We're working on that" and declined to comment further.