In politics, money can’t always buy you love

Herb Kohl, owner of the Milwaukee Bucks and a Wisconsin Democrat, did that in 1988, spending about $4 million of his own money for the seat he still holds.

And if Pagliuca spends $10 million of the fortune he made from Bain Capital’s investments, he will not come close to the record for personal wealth spent in pursuit of membership in the exclusive Senate club. That honor goes to Democrat Jon S. Corzine of New Jersey, the former head of Goldman Sachs, who spent $62 million to win a seat in 2000 and is now running for reelection as gover nor of the Garden State.

Pagliuca is the latest megamillionaire eager to start his political career at the top, in this case a Senate seat that has been held by political giants, including Kennedy, future presidents John F. Kennedy and John Quincy Adams, and Daniel Webster.

Pagliuca enters the race almost a blank slate, and his money will allow him to use television advertising to shape his image and highlight his business background as an asset in dealing with the nation’s economic problems.

Seven years ago, Mitt Romney, Pagliuca’s former partner at Bain, showed that wealth can help, spending $6.3 million of his own fortune in winning the governor’s race. But Pagliuca’s climb will be much steeper: Romney had already established a public presence in Massachusetts, spending $7 million of his own money in a losing challenge to Kennedy in 1994 and leading the 2002 Winter Olympics in Utah before entering the governor’s contest.

For every captain of commerce who has succeeded in politics, there are many who have failed. Money provides an entree, but is no substitute for experience in the art of politics, and it is hardly a guarantee of success. With a very short campaign season for the primary, Pagliuca faces many challenges, only some of which he can surmount by writing checks, analysts say.

“You can’t just spend money and get there; you have to have something to say,’’ said Robert M. Shrum, a leading Democratic strategist whose past clients include Kennedy and self-funders Kohl, Corzine, and John Edwards, who was a political neophyte in 1998 when he spent about $3.2 million of a fortune made as a trial lawyer to win a North Carolina Senate seat.

Pagliuca must convince voters that, despite his wealth, he understands, cares about, and will do something to help them through the economic downturn, said Shrum, who helped elect 15 of the sitting Democratic senators in 2004, his last election before leaving political consulting for academia.

“The big question is, can he connect with people?’’ Shrum said.

Shrum had a hand in one of the great self-funded candidate debacles, investor Al Checchi’s 1998 campaign for governor of California. Checchi spent $40 million of his own money and finished a distant third in the primary.

“Wealthy, self-financed candidates occasionally do win, but they much more often lose,’’ said Jennifer A. Steen, who teaches political science at Yale and has written a book on self-funded congressional hopefuls. Lack of political experience is a major reason for their failure, she said, and very often trumpeting business expertise is a flat campaign message, especially in races for a legislative, rather than executive, post.

Still, Steen said, Pagliuca could benefit, because the compressed election season - the Democratic primary is Dec. 8, with the special election Jan. 19 - will force the candidates to rely more heavily on television advertising. Indeed, Pagliuca’s ads are already in heavy rotation.

Will Keyser, a Pagliuca campaign spokesman, said the candidate’s financial resources will allow him to tell voters about his life story, his values, and his policy positions, particularly regarding the economy, which Keyser called “the biggest issue facing the country.’’

“Steve is somebody who has been a lifelong investor and whose life’s work has been in building and growing businesses and understanding the relationship between businesses and the financial markets,’’ Keyser said. “On that core issue, he’s got a great set of experiences and a lot to offer.’’

Pagliuca’s past support of Republican candidates and his Republican registration - he became a Democrat in 1998 - could be a problem, particularly with the more partisan voters who will cast ballots in the Democratic primary.

“In the primary, the electorate is made up of the most ardent constituencies and the party loyalists,’’ said Raymond J. La Raja, professor of political science at the University of Massachusetts at Amherst. Besides his Democratic bona fides, Pagliuca’s investing record and the companies he has been associated with will be carefully scrutinized by core party constituencies, such as organized labor and environmental activists, La Raja said.

Romney’s 2002 triumph was a rarity in Massachusetts, where voters have usually rejected wealthy, self-funded candidates for high office. Two of the candidates who ran in 2006 to succeed Romney - Lieutenant Governor Kerry Healey and Democrat and investor Christopher Gabrieli - each spent more than $9 million of their personal wealth in losing efforts.

“They have a money advantage, and that’s obviously important,’’ said Michael Bailey, professor of political science at Georgetown University. “But money can’t buy you political experience and the knowledge of how to talk to constituents and reporters or how to respond in an appropriate way in debates.’’

“People are a lot nicer in the board room than they are in the debates,’’ Bailey added.

Though each of the candidates vying to succeed Kennedy faces a stature gap, analysts say, Pagliuca has a particular challenge running in a state that has produced so many senators who were influential national figures.

“Ted Kennedy was the most experienced politician in America,’’ La Raja said. “And it’s not clear that voters will want to replace him with someone in politics for the first time.’’

Shrum added, “Nobody’s going to fill Teddy’s shoes, but voters in Massachusetts want somebody who will be taken seriously.’’