Newspaper reports have revealed that some lottery publicity efforts could violate a state law limiting the lottery's advertising budget.
In addition, some have accused Malone of loading the state's lottery with cronies, while at the same time downsizing layers of management.
Dephillippo, a former Vice President at Fileen's Basement clothing chain, says that both charges are off-base and adds that whatever Malone's hiring practices are, they have worked. In business, he says, that's all that matters.
"If [the lottery's success] has anything to do with Joe's hiring people that he knows or people from his college class, then he should have hired the whole damn class," Dephillippo says.
While Malone may champion cost-cutting reforms that bare resemblance to those forwarded by some of the nation's conservative Republicans, he is careful to distance himself from them.
Instead, the former defensive lineman likens himself to more progressive Republicans such as Sen. Connie Mack (R-Fla), former Vice-Presidential Candidate Jack Kemp and New Jersey Gov. Christie Todd Whitman.
Malone says that the 1992 Republican Convention in Houston was a case where he was alienated by his party's conservative fringes.
"I felt so uncomfortable," Malone says. "That was not the Republican party that I want to be a part of."
His Own Niche
While Malone has an image of fiscal conservatism and social liberalism, it is an image that he shares with the Weld-Cellucci administration.
Although Malone is careful not to discredit the tremendously popular executive-duo, he is making an effort to create a gap between himself and the Lt. Governor.
"If Bill Weld were to announce today that he was going to run for a third term, I would sign up to support him immediately.... Now it's a case of where do we go from here and who's the best person to lead the state," Malone says.
But keeping with the policy he began during his first campaign against Kennedy, Malone, discussing only his own strengths, will not speak of Cellucci's weaknesses.
But many of Malone's friends are more candid about the differences.
Channel Five's Lynch says that the treasurer's aggressive attacks in the name of cleaning up government separate him from the rest of the pack.
"He didn't follow the normal path that people do when they get to Beacon Hill," Lynch says. "They aren't independent thinkers like Joe is."
And Shamie, still protective of his protege, argues that Malone's ability to cleanup state government without regard for consequences separates him from his colleagues.
"A lesser politician would let things slip under the carpet," he says.