It appears this peculiar streak will end on November 7, but no matter who gets elected – Republican Kerry Healey, or Democrat Deval Patrick – the result is sure to be momentous, for the state has never before elected a female or an African-American to the governorship.

Why does arguably the most liberal state in the Union have such a proclivity for white males, most recently conservative Mormon businessman Mitt Romney? And does Patrick’s probable election represent a liberal bastion coming to its senses? More pointedly, is it the dawning of a new era in a state often regarded as hostile to African-Americans?

“Beleaguered working-class voters readily support a liberal Democratic congressional delegation that delivers the federal bacon for key industries like health care and academia,” explains Massachusetts political analyst Jon Keller, who contributes to local television station CBS-4, news radio station WBZ, The Boston Herald, and Boston Magazine.

“But they have (until this year) proven eager to keep one anti-tax Republican in to act as a check on the legislature, which is widely regarded as a bunch of featherbedders, even though incumbents rarely lose. Romney won in 2002 for this very reason. His opponent [state treasurer Shannon O’Brien] was seen as a hostage to the Beacon Hill establishment, and Romney was viewed as an outsider who would keep them honest and generate jobs.”

In some ways the roles have been reversed this year. It is Healey, Romney’s lieutenant governor, who represents a cog of a failed political machine. She has tried to separate herself from her boss, whose popularity has plummeted in the Bay State over the past year as he’s toured the nation to gauge his chances at the 2008 presidency, but her attempts seem to be too little, too late. In Romney’s absence Healey has had to answer for many of the problems that now plague the state, such as slow economic recovery and one of the highest costs of living in the country.

On the other hand, Patrick, a former federal civil rights lawyer, has never run for elected office. His election would be “an endorsement of a fresh face from outside the state’s clubby political culture,” according to Keller, even though his politics are mostly “standard Democratic Party boilerplate.”

Some experts believe Patrick’s popularity is driven by more than just politics. “I think many have wanted to elect a black governor for a while, says Harvard sociologist Christopher Winship, whose research includes issues of race and public policy. “His wealth and his obvious ability to play with the big boys make him appear very competent.”

When Patrick declared his candidacy, when Massachusetts voters had no concept of who he was and what he stood for, it nonetheless “thrilled liberals to be able to finally have a black candidate,” according to Keller. However, he points out that Patrick has barely mentioned race at all, “letting the obvious speak for itself.”

Patrick held a large advantage over Healey in an October 24 poll of 400 Massachusetts voters. Suffolk University and WHDH Channel 7 reported that he led 53 percent to her 26 percent, with 11 percent of voters remaining undecided (two other candidates are also running, Independent Christy Mihos and Green Rainbow nominee Grace Ross). Although Healey had narrowed Patrick’s lead to 13 percent earlier in the month, a series of negative ads and a possible leak by her camp of controversial information about Patrick’s family have driven down her popularity.

Interestingly, some feel that Healey had no choice but to attack Patrick, who was so much of an unknown that certain aspects of his career were controversial. He has drawn criticism for his handling of an affirmative action case in New Jersey in the 1990s and his defense of a man who killed a state trooper in Florida. During the primary many of his opponents took the same aggressive tack as Healy, particularly in debates. Furthermore, as Keller points out, Patrick, too, has run negative ads - “some with dubious ‘facts’ in them – but he has had surrogates handle those, while the ads featuring him make Mr. Rogers look edgy.”

In many ways Healey and Patrick are cut from the same cloth. Both grew up poor, she in Florida, he on Chicago’s South Side, and both came to Massachusetts for educational purposes. Patrick first arrived as A Better Chance scholarship student at Milton Academy and then went on to Harvard, from which he graduated in 1978. He earned a law degree from Harvard Law School in 1982. Healey also attended Harvard, on a scholarship, graduating in 1982. She went on to earn both a PhD in political science and a law degree from Trinity College, Dublin.

Patrick has practiced law in a number of different venues. As an attorney for the NAACP in the 1980s, he first encountered Bill Clinton, who was being sued in Arkansas in an election rights case. In 1994 Clinton named Patrick, by then in private practice, the U.S. Assistant Attorney General for Civil Rights. Patrick was very involved with issues relating to prisoners’ rights and affirmative action.

After working in private practice in Boston from 1997-99, Patrick became executive vice president, general counsel, and corporate secretary of the Coca-Cola Company. He has also served on the board of directors for United Airlines and Ameriquest Financial, the latter due to his history of fighting predatory lending.

Healey has worked in the field of criminology, and has also taught the subject at local colleges in Massachusetts. Through much of the 1990s, she was a law and public safety consultant at Abt Associates in Cambridge. According to her official campaign website, while there she “conducted extensive research for the U.S. Department of Justice related to child abuse and neglect, domestic violence, gang violence, victim and witness intimidation and the prosecution of drug crimes.”

In both 1998 and 2000, Healey ran unsuccessful campaigns for the 6th Essex State Representatives District of Massachusetts, each time losing to incumbent Michael Cahill by about a 30 percent margin. She served briefly as chair of the Massachusetts Republican Committee before Mitt Romney tapped her as his running-mate in 2002.

Healey’s husband, Sean, is the CEO of a successful asset management firm, and is believed to be worth at least $100 million. He has reportedly sunk millions of dollars into her campaign. The Boston Globe recently reported that Sean Healey, a registered Republican, supported the participation of illegal immigrants in the workforce when he was appointed to President Bush’s 47-member Export Council last year. This is notable because Kerry Healey has been quite vocal in calling for a crackdown on illegal immigration. She differs on this issue with Patrick, who supports giving illegal immigrants drivers licenses and in-state tuition at state colleges and universities.

Healey and Patrick are both pro-choice (a virtual requirement for any statewide political candidate in Massachusetts), and each supports stem cell research. On the prominent Massachusetts issue of gay marriage, Patrick fully supports the Supreme Judicial Court’s landmark 2003 ruling, while Healey favors “civil unions” for homosexuals rather than universal marriage.

Healey, like most of her Republican predecessors, would like to reinstate the death penalty in Massachusetts. Patrick, who has prosecuted capital cases and has also advocated for prisoners on death row, is opposed to it.

Earlier this fall Healey ran a controversial commercial, now notoriously known as “the cop killer” ad, highlighting Patrick’s 1985 work for the NAACP Legal Defense Fund, in which he successfully argued to overturn the death sentence of a man convicted of killing a Florida state trooper. The ad features a shadowy reenactment of the cop’s murder, then asks “While lawyers have the right to defend cop killers…do we really want one as our governor?”

Another ad, which criticizes Patrick’s long-term advocacy on behalf of convicted rapist Benjamin LaGuer, shows a woman seemingly being followed by a sexual predator in a dark parking garage. The ad features a brief clip of Patrick praising LaGuer’s eloquence and intelligence in an interview, then tells us, “Deval Patrick: He should be ashamed…not governor.”

Massachusetts voters responded quite negatively to these ads in polls, saying that they “crossed the line.” In an October one poll put out by CBS-4 and The Boston Globe, 45 percent of voters said they were less likely to vote for Healey because of her negative ads.

Patrick, meanwhile, has enjoyed his popularity boost while saying very little at all. Since he has never run for any elected office, his platform is partly based on his outsider status and immunity to Massachusetts’ notorious insider politics.

Says Keller, “Patrick has run the ultimate feel-good campaign, largely vague on specifics, but big on making voters (especially baby-boomers) feel good about themselves for supporting him. At one point he had a line in his stump speech about how he was no JFK, no Bobby Kennedy, no Dr. King, but he understands the power of idealism.”

Four years ago, Mitt Romney ran on a similar outsider platform, and voters were filled with hope and optimism. Yet as his term wore on, he grew increasingly frustrated with the state’s extremely liberal Senate and House of Representatives and their inability to compromise. Perhaps Patrick’s more liberal leanings will prevent a similar clash, though there’s also the possibility that his inexperience with the Bay State’s tricky political maneuverings could overwhelm his ability to take a stand against the powerful House and Senate.