For four decades, James A. “Jac” Cales Jr. was a fixture on the judicial halls of Hampton Roads, albeit not one to take himself too seriously.

As Portsmouth commonwealth’s attorney for a decade in the 1970s, he would lean back in his chair, his hands folded over his stomach and nod vigorously when a defendant in a drug case admitted something incriminating. He later served for three decades as a General District and Circuit Court judge, retiring officially in December.

So, it may be fitting that on May 1, while filling in temporarily, Cales issued what could be the most important decision of his long legal career. It is a decision that is turning Virginia’s transportation funding on its head.

Cales decided that a plan to have a private developer toll users for $2.1 billion in tunnel upgrades in crowded Hampton Roads is unconstitutional. Only the state has the power to tax and that’s what tolls really are, Cales ruled.

If his ruling holds, a number of critically important highways that involve privately operated facilities, such as parts of Interstate 495 in Northern Virginia, Route 895 near Richmond and a proposed $1.3 billion toll road from Petersburg to Suffolk, could be affected. State contracts for all of them could be voided.

If so, it would be a huge defeat for Gov. Robert F. McDonnell and earlier governors who have made good use of the Public-Private Transportation Act of 1995 to push ahead with highways that the tax-averse state otherwise was too short of money to build.

Cales’s case involved legal challenges to using the private toll road concept to pay for upgrades at the Downtown and Midtown Tunnels underneath the Elizabeth River connecting Norfolk and Portsmouth.

The key issues are electronic tolls that are supposed to kick in next February. Off-hour tolls for cars are $1.59 and go up to $1.84 during rush hour. Trucks would have to pay $7.36 during peak times. Business officials and commuters, many working in blue-collar jobs, are angry about the new expense. The tunnels used to be toll affairs years ago and the fees were much lower.

The pressure is on to void Cales’s ruling, lest it result in massive scrambling of road plans. Transportation Secretary Sean Connaughton, a big fan of the PPTA, warned of serious possible repercussions when he met with lawmakers Monday. “This is not consistent with almost 240 years of building toll facilities in the commonwealth of Virginia, Connaughton told the House Appropriations Committee, according to the Richmond Times Dispatch.

Cales’s ruling is due to be appealed to the State Supreme Court, but in the interim, he has refused to stay his decision. One possible outcome is that the state would be stuck with a lot of expenses that have already been paid, such as $706 million for the Elizabeth River tunnels. In all, the state could be on the hook for $3.5 billion.

The General Assembly would also be forced to perform a heavy-duty rethink of how it funds roads.

But that may be a good thing. The PPTA, heralded as a rare pioneering effort for Virginia, has been used far beyond its intended purpose. It was supposed to be a way to supplement traditional road funding. Instead, skin-flint legislators who hate “taxes” have used the PPTA as a way to fund roads through tolls instead with private companies assuming much of the risk. Democrats and Republicans alike liked this scheme of having your cake and eating it too.

The outcomes have not always been good. A relatively short toll road southeast of Richmond, the Route 895 Pocahontas Parkway, has been so underused and underfunded that it was sold off to Australia’s Transurban firm, which recently announced it was selling it to a consortium of European banks because it wasn’t making money.

Peter Galuszka blogs at Bacon’s Rebellion. The Local Blog Network is a group of bloggers from around the D.C. region who have agreed to make regular contributions to All Opinions Are Local.