Between 2003 and 2005, Mason repeatedly awarded no-bid work to Qwestcom Graphics Inc. to print court documents, brochures and manuals, according to county payment records obtained by Investigator Tom Meyer.
Qwestcom has also performed more than $32,000 worth of work for other county agencies since it opened in 2001.
The payments raise ethical questions because one of Qwestcom's investors is Thomas Day Jr., a longtime friend of Mason and the Bedford Municipal Court clerk.
Mason and Day are also partners in a separate company, Victory Communications, which they launched in 2002, to provide campaign support and strategy for political candidates, according to interviews and financial disclosure statements by Mason.
Under state ethics law, public officials are prohibited from awarding work to a business partner or to any other companies that the business partner owns, said Jennifer Hardin, chief advisory attorney for the Ohio Ethics Commission.
Violating the law is a fourth-degree felony, punishable by up to 18 months in prison and a $5,000 fine.
At issue is when Day, a Cuyahoga County Democratic Party insider, became a partner in Qwestcom.
The company's president, Joe Krause, told Meyer that Day became a silent partner in either 2004 or 2005, but that he could not recall the exact date.
Krause also said Day introduced him to Mason and that he considers the prosecutor a friend.
Krause declined to say whether that friendship got him printing work from the prosecutor's office.
For his part, Day told Meyer that he became a partner in Qwestcom in either 2004 or 2005, although, "for some reason, '05 hits me in the head. I could be wrong."
Day said he was not immediately available to find documents to answer the question.
Mason denied any wrongdoing but said he will seek an opinion from the Ohio Ethics Commission in response to questions from Meyer about the work and the business relationship.
"Qwestcom Graphics has done no business with my office since 2004, five years ago," the prosecutor said in a statement. "I do not think there has been any ethics violation here."
Payment documents from the Cuyahoga County Auditor's office, however, indicate that Qwestcom was paid $125 on April 1, 2005, for printing work.
If the Ohio Ethics Commission determines there is wrongdoing in a case, it typically refers the case to the lead law enforcement agency in the county.
Since that is Mason's office in this instance, it would likely be up to a Common Pleas Court judge to appoint a special prosecutor to pursue the matter.