In 1997, Massachusetts's only harness racing track,[2] Foxboro Park, was closed after a legal dispute between its owner, Robert Kraft, and its operator, Charles Sarkis.

The Racing Commission issued a conditional license for Piontkowski's proposed track in November 1997, with a targeted opening date of May 1998.

[8] The project was nevertheless granted a two-month extension of its financing deadline, raising criticism that commissioners were being too lenient with Piontkowski, who had previously served as the Racing Commission's chairman.

[18] Plainridge Racecourse faced criticism from the beginning, with industry observers and Racing Commission chair Robert Hutchinson arguing that the track's live racing schedule was nothing but an excuse to justify a lucrative off-track betting operation and a potential racino; a large room in the grandstand was set aside for the installation of as many as 400 slot machines.

[20] The commission found that Giuliano did not actually own the land, but only held an option to buy it from a Boston investment company, Realty Financial Partners (RFP), which had financed the purchase.

[21] After Giuliano failed to exercise his option to buy the track, RFP claimed control and served an eviction notice on Piontkowski.

Piontkowski consistently supported proposed legislation to authorize slot machines at the state's four racetracks, touting plans for a $180-million expansion of Plainridge.

[35] The track began construction of a 1,000-car parking garage in late 2012, hoping to demonstrate to the Gaming Commission that its proposal would be the quickest to open and begin generating tax revenue.

The bid overcame competition from two other applicants, a Cordish Company slot parlor proposed for Leominster, and a former greyhound racing track in Raynham.