Friess - who made his money managing the $15.7 billion portfolio of the Brandywine Fund - has put up a "good chunk" of the nearly $1.5 million spent by a super PAC backing Santorum, the Red, White, and Blue Fund.
This week, he upped the ante, sending notes to 5,000 friends and colleagues pledging to match their donations - up to a half-million dollars - in advance of Saturday's South Carolina primary.
But while Friess declines to put a specific figure on his contributions, that total has put him in league with such Republican donors as casino magnate Sheldon Adelson - who cut a $5 million check to a super PAC supporting Newt Gingrich this month - and Jon Huntsman Sr., who funneled millions into his son's now-aborted presidential bid.
Together, they have single-handedly buoyed once-trailing campaigns, saturated airwaves with campaign ads, and raised the hackles of groups who want to curb big money's role in picking presidents.
"They're in a class of a couple hundred Americans that can keep a presidential candidate afloat all by themselves," said James Browning of Common Cause. "It warps the political process."
Friess, an outspoken evangelical Christian, veteran supporter of conservative causes, and ally of the billionaire industrialist Koch brothers, defends his right to bestow his largesse on whomever, and to whatever degree, he chooses.
"My donations are destined for people who can reshape America and rejuvenate it back to its traditional value system," he said.
Friends say Friess' support for Santorum exhibits the flair for showmanship for which he has become known.
A tall man with the weathered face of an outdoorsman, he delights in stunts such as the one he pulled at his 70th birthday party, said Molly F. Greene III, friend and cofounder of the Christian charity Water Missions International.