CHARLES A. FRUEAUFF FOUNDATION.

>> THIS WEEK ON TO THE CONTRARY... FIRST, IS DONALD TRUMP THE ANSWER TO THE G.O.P.

GENDER GAP?

CAN TRANSGENDER WOMEN REALLY UNDERSTAND SEXISM?

BEHIND THE HEADLINES SURE CLAIRE McCASKILL TELLS US IT'S OK TO BE STRATEGIC.

[♪♪♪] I'M BONNIE ERBE.

WELCOME TO THE CONTRARY.

UP FIRST, DONALD TRUMP COURTS WOMEN.

HE IS WORKING THE WOMEN'S VOTE AND IT APPEARS TO BE PAYING OFF.

A POLL SHOWS 60% OF FEMALE REPUBLICAN VOTERS HAVE A FAVORABLE VIEW OF HIM.

STILL HE FACES CHARGES OF SEXISM DUE TO PAST INSULTS HE HURLED AGAINST PARTICULAR VICTIM.

HIS DAUGHTER IVANKA SAYS HER FATHER IS MISUNDERSTOOD WHEN IT COMES TO WOMEN'S ISSUES.

HE CHERISHES AND PROTECTS WOMEN AND JABS JEB BUSH FOR SAYING THE GOVERNMENT SPENDS TOO MUCH MONEY ON WOMEN'S HEALTH ISSUES.

AND TRUMP BOASTS THAT HE PAYS HIS FEMALE WORKERS BETTER THAN MEN.

POLLING SHOWS TRUMP IS FAR BEHIND DEMOCRATIC FRONTRUNNER HILLARY CLINTON IN A POTENTIAL MATCHUP WHEN IT COMES TO FEMALE VOTERS.

SO CLARA WE KNOW THAT THE REPUBLICAN PARTY HAS A WOMAN PROBLEM.

IS TRUMP THE ANSWER?

>> FIRST OF ALL TRUMP IS A PROBLEM SOLVER FOR THE MEDIA CASH FLOW AND RATINGS SLUM DURING SUMMER.

HE IS THE ENTERTAINMENT FEATURE HERE AND THE GOOD THING ABOUT HIM HE IS SOLVING THE PROBLEM IN TERMS OF THROWING IDEAS ON THE TABLE THAT DISRUPT NOT ONLY CONSERVATIVES BUT THE TALKING POINTS THAT THEY ARE SO MARRIED TO.

>> IF HE IS THE ANSWER TO THE REPUBLICANS WOMEN'S PROBLEM THEN THE REPUBLICAN PARTY IS HAVING DEEPER PROBLEMS THAN WE REALIZE TODAY.

[LAUGHTER] >> I THINK HE IS INTERESTING IN THAT HE IS TAPPING INTO SOME SORT OF ANGST AMONG A LOT OF VOTERS.

AND NOW YOU HAVE TWO CANDIDATES HIM BEING ONE WHO IS SAYING SOMETHING THAT WOMEN WANT TO HEAR AND WOMEN WHO ARE TRYING TO GO VIRAL WITH THE MESSAGE ABOUT THEIR SUPPORT WE HAVE TO TAKE SOMETHING THERE.

>> I THINK THE MOST PORPOISE THING TO UNDERSTAND ABOUT WOMEN AND WHY THE REPUBLICANS ROAST THE WOMEN'S VOTE IS BECAUSE WOMEN VOTE FOR PARTY OVER GENDER.

OVER AND OVER AGAIN.

SO ONE OF THE THINGS THAT HAS HAPPENED IN RECENT YEARS AND YOU SEE THIS EVEN IN THE POLLING AMONG REPUBLICAN WOMEN FOR CARLY FIORINA IT'S NOT NECESSARILY AS STRONG AS TRUMP BECAUSE SHE IS BEHIND TRUMP IN THE POLLS.

>> BUT, BUT, WOMEN VOTING FOR PARTY NOT GENDER.

WOMEN, I'VE ALWAYS THOUGHT LIKE MEN VOTE THEIR ECONOMIC INTERESTS.

WOMEN ARE 20% MORE LIKELY TO VOTE DEMOCRAT THAN REPUBLICAN.

WHY?

10 TO 20% OF THEM ARE MORE LIKELY TO BE RELYING ON FEDERAL SERVICES TO GET BY.

AND IT IS THE SAME WITH MEN.

MEN HAVE MORE MONEY THAN WOMEN AND AND REPUBLICANS ARE FOR TAX CUTS SO THEY FOLLOW THEIR ECONOMIC INTERESTS.

>> THAT IS NOT NECESSARILY TRUE.

THE GENDER GAP WAS CREATED BECAUSE MEN STARTED VOTING REPUBLICAN.

SO IT'S IMPORTANT TO UNDERSTAND THAT IT WAS THE SHIFT IN MEN'S VOTES DURING RONALD REAGAN'S PRESIDENCY THAT BEGAN THIS MOVEMENT OF MEN MORE INTO THE REPUBLICAN PARTY AND WOMEN REMAINING WITHIN THE DEMOCRATIC PARTY.

>> BUT TRUMP IS TALKING ABOUT JOBS AND ECONOMIC ACCOMPLISHMENTS.

AND WOMEN ALSO, I THINK, RESPOND TO HIS MEDIA DAZZLE AND TELLING IT LIKE IT IS.

>> REPUBLICAN WOMEN DO.

WE'RE SEEING 60% OF REPUBLICAN WOMEN HAVING A FAVORABLE VIEW OF HIM.

BUT REPUBLICAN WOMEN DO NOT MAKEUP THE MAJORITY OF THE WOMEN'S VOTE.

THAT IS WHY DEMOCRATS WIN.

AND IT'S NOT WHITE MARRIED WOMEN AS YOU MENTIONED HAVE NOT VOTED REPUBLICAN FOR SIX ELECTIONS NOW.

AND THE FIRST TIME THEY DID, WAS IN THE FIRST TIME THAT A REPUBLICAN EVER WON THE WOMEN'S VOTE WAS IN 1980 WITH RONALD REAGAN.

BUT, IT'S MAINLY WOMEN OF COLOR, SINGLE WOMEN, WIDOWED WOMEN WHO VOTE DEMOCRAT AND THERE ARE WAY MORE OF THEM THAN MARRIED WHITE WOMEN WHO VOTE REPUBLICAN.

ARE THOSE WOMEN GOING TO VOTE FOR TRUMP?

>> HELL, NO.

REALLY, NO.

NOT IN ANYWAY SHAPE OR FORM.

AND YOU ARE RIGHT THEY ARE A CRITICAL PART OF THE RISING AMERICAN ELECT TORE RAT.

SINGLE WOMEN, WOMEN OF COLOR AND BLACK WOMEN WHO HAVE THE HIGHEST VOTER PARTICIPATION RATE IN THE NATION WILL NEVER GIVEN TRUMP THE CHANCE PARTICULARLY IN VIEW OF THE INSULTING THINGS HE SAID IN THE PAST.

THE POLLS LOOK DIFFERENT THAN IN THE STATES.

WHEN YOU LOOK AT THE POLLING IN IOWA, TRUMP HAS A 19% GENDER GAP IN HIS DISFAVOR IN IOWA AMONG LIKELY CAUCUS GOERS WHO ARE REPUBLICANS.

SO IT IS NOT TRUE THAT HE IS JUST WILDLY GAINING REPUBLICAN WOMEN SUPPORT ACROSS THE BOARD.

HE IS GAINING THOSE WHO ARE NOT SEEING HIM ORTHOS NOT YET TAKING THE PRESIDENCY AND THE ELECTION SERIOUSLY.

>> AND WHAT ABOUT HIS QUOTE THAT WE USED IN THE TAPED PIECE SAYING HE WANTS TO PROTECT WOMEN.

IS THAT -- I KNOW THAT IS NOT WHAT MIDDLE AND OLDER AGED FEMINISTS WANT TO HEAR.

IS THAT WHAT YOUNG WOMEN AND CONSERVATIVE WOMEN WANT TO HEAR?

THAT IS LANGUAGE THAT THEY USED IN THE 1800'S TO MAKE RULES AGAINST WOMEN WORKING.

>> WELL, I THINK SOME MAY INTERPRET PROTECTION TO MAKE MAKING SURE WE HAVE AN EQUAL SAY IN THE MARKET AND THAT WE HAVE ACCESS TO THE OPPORTUNITIES THAT ARE THERE.

GETTING BACK TO YOUR POINT ABOUT WOMEN BLACK WOMEN AND VOTING, I THINK THERE IS A DUEL OF YOUNG BLACK WOMEN WHO TALK ABOUT WOMEN STUMPING FOR TRUMP AND TWO BLACK WOMEN AND THE VIDEOS ARE GOING VIRAL AND WHAT THEY ARE TALKING ABOUT IS IMMIGRATION.

AND FROM A PEOPLE OF COLOR PERSPECTIVE THE IMMIGRATION DEBATE AND WHEN IT COMES TO ECONOMICS AND JOBS IS A HOTBED DISCUSSION TO HAVE ABOUT WHETHER PEOPLE OF COLOR THINK THAT CHANGING OUR IMMIGRATION POLICY IS GOING TO BENEFIT THEM IN THE WORKPLACE.

>> TRUMP TAPPED INTO THAT.

ON THE DEMOCRATIC SIDE THAT THERE ARE FEWER AGAINST HIS VIEWS THAN ONE MAY THINK.

AND I THINK THAT IS AN INTERESTING TAKE AWAY FROM ALL OF THIS.

BUT OVERALL, TRUMP IS A PHENOMENON.

OBVIOUSLY I THINK HE HAS DONE A LOT OPPORTUNITY THE WOMEN FRONT IN HIS BUSINESSES.

BECAUSE HE IS FROM THE PRIVATE SECTOR.

THE REAL ESTATE SECTOR, CASINOS AND SO OBVIOUSLY HE HAS OFFERED A LOT OF OPPORTUNITY IN THAT AREA.

BUT HE IS NOT A SUSTAINABLE CANDIDATE I DO NOT SEE.

>> HIS STAND ON PLANNED PARENTHOOD.

ONE HAND HE JABBED JEB BUSH FOR SAYING WOMEN DO NOT NEED BILLIONS OF DOLLARS SPENT ON HEALTHCARE.

ON THE OTHER HAND HE IS FOR DEFUNDING PLANNED PARENTHOOD.

WHERE DOES THIS LEAVE HIM?

AND IN TERMS OF GETTING THE WOMEN'S VOTE WHO SO MANY MILLIONS OF POOR WOMEN RELY ON PLANNED PARENTHOOD FOR CANCER SCREENINGS AND THE REST OF IT.

>> MANY REPUBLICAN WOMEN ARE IN FAVOR OF DEFUNDING PLANNED PARENTHOOD WE HAVE TO PUT THAT ON THE TABLE.

THE WOMEN HE IS GOING TO BE AK TRAING PROBABLY DO AGREE ON THE PROPOSITION OF DEFUNDING PLANNED PARENTHOOD.

THAT BEING SAID, HIM SORT OF HITTING JEB BUSH ON YOU KNOW HIS WHAT WAS CLEARLY SORT OF AN IMPRECISE STATEMENT ABOUT HIS OWN VIEWS ABOUT WOMEN'S HEALTH ISSUES SAYING THAT $500 MILLION IS TOO MUCH TO BE FUNDING ON WOMEN'S HEALTH, IS, I THINK, HYPOCRITICAL.

WE KNOW THAT DONALD TRUMP HAS SPENT YEARS SAYING HORRIFIC THINGS ABOUT WOMEN IN ALL SORTS OF VENUES AND INTO THE OUGHT BIOGRAPHIES.

THE IDEA THAT HE WILL BE GOOD FOR WOMEN, I THINK IS SORT OF A FALSE NOTION.

>> AND NOT PARTICULARLY ON THE WOMEN'S HEALTH ISSUES.

>> I MEAN CLEARLY HE UNDERSTANDS.

SOMEBODY HAS GOTTEN TO HIS EAR THAT IT'S IMPORTANT TO HAVE THE WOMEN'S VOTE.

SO I THINK HE WAS BEING STRATEGIC IN PULLING OUT THAT IMPRECISE STATEMENT TO MAKE POLITICAL GAINS.

IT WAS A SHREWD MOVE.

BUT HE IS USING CELEBRITY TO HIS ADVANTAGE BUT IT WILL CATCH UP WITH HIM.

HE HAS NO MEAT ON THE POLICY ISSUES AND THAT IS NOT QUALIFICATIONS TO BECOME PRESIDENT OF THE UNITED STATES.

>> TELL ME YOU BROUGHT UP TRUMP AND IMMIGRATION WHICH IS, OF COURSE, AT THIS POINT SEEMS TO BE HIS LEAD DRAW.

ARE REPUBLICAN WOMEN AS ANTI-IMMIGRATION AS REPUBLICAN MEN ARE?

>> THEY MAY NOT BE AS ANTI-IMMIGRATION AS IT MAY SEEM.

I THINK THEY WORRY ABOUT YOU KNOW SECURITY REASONS.

THE KINDS OF PEOPLE COMING INTO OUR COUNTRY AND WHAT THAT LOOKS LIKE.

BUT THERE ARE A LOT OF LIBERTARIANS AND CONSERVATIVES WHO WELCOME IMMIGRATION.

AND IT'S IMPORTANT TO RECOGNIZE THAT IMMIGRATION IS NOT THE BAD THING WE'RE TALKING ABOUT ILLEGAL IMMIGRATION.

>> THE EVAN JESS CALC COMMUNITY IS PRO LEGALIZATION AND KEPT QUIET DURING THE PHASE HOPING IT WILL PASS BUT IN ADDITION TO SOME OF THE TOP PUNDITS WILL BE PRO IMMIGRATION REFORM SO THEY COME OUT AGAINST DONALD TRUMP ON THE VIEWS.

>> AND ALSO THE REPUBLICAN BUSINESS COMMUNITY THAT WANTS CHEAP LABOR.

THERE ARE ELEMENTS OF THE REPUBLICAN PARTY AND THEN THE REPUBLICANS WHO LIKE DEMOCRATS WANT MORE VOTES FOR THE PARTY.

>> ABSOLUTELY.

THE PROGRESSIVES THAT FEEL THAT ILLEGAL IMMIGRANTS OR IMMIGRANTS IN GENERAL ARE TAKING AMERICAN JOBS.

DATA PROVES OTHERWISE.

BUT THAT FACT REMAINS.

AND ALL YOU HAVE TO DO IS GO TO THE AGRICULTURAL CENTERS IN CALIFORNIA AND SEE ALL THE VEGETATION ISSUES THEY HAVE HAD TO SEE HOW THE BORDER CLOSINGS AFFECTED THEIR BUSINESSES.

>> ALL RIGHT.

LET US KNOW WHAT YOU THINK.

FOLLOW ME ON TWITTER @BONNIEERBE.

FROM THE WOMEN'S VOTE TO SEXISM AND TRANSGENDER WOMEN.

PRESIDENT OBAMA THIS WEEK APPOINTED THE FIRST OPENLY TRANSGENDER WOMAN OF COLOR TO THE WHITE HOUSE STAFF.

RAFFI FREEDMAN-GURSPAN'S ROLE AS AN OUTREACH AND RECRUITMENT DIRECTOR IS A VICTORY FOR THE TRANSGENDER COMMUNITY.

BUT AS TRANSGENDERED WOMEN ACHIEVE MORE POWER SOME BY BIOLOGICAL WOMEN WONDER WHETHER TRANSGENDER WOMEN SPENT PART OF THEIR LIVES AS MALES UNDERSTAND SEXISM OR CAN BE CLAIM TO BE FIGHTING AGAINST IT.

COMMENTATORS NOT HAVING STARTED LIFE AS WOMEN TRANSGENDERED WOMEN HAVE NOT SUFFERED BEING SCRUTINIZED SEXUALLY FROM MEN BY THE START OR BY THE PAY GAP IF THEY STARTED CAREERS AS METROPOLITAN OR THE FEAR OF RAPE AS YOUNG GIRLS.

Dr. JONES I'M FASCINATED AS WE SEE THIS OBAMA APPOINTMENT AND CAITLYN JENNER OUT THERE AS A WOMEN'S RIGHTS ADVOCATE THERE WAS A WOMAN IN JUNE WHO WROTE A PIECE FOR "THE NEW YORK TIMES" ABOUT CAITLYN JENNER CLAIMING TO BE A WOMAN'S RIGHTS ADVOCATE AND SAID SHE CRINGED WHEN SHE CAME OUT.

AND A LOT OF WOMEN FEEL THIS WAY.

IS THERE GOING TO BE A COMFORTABLE OR UNCOMFORTABLE RELATIONSHIP BETWEEN WOMEN'S RIGHTS ADVOCATES AND TRANSGENDER RIGHTS ADVOCATES OR NOT?

>> THERE MIGHT BE.

AND I HOPE THERE ISN'T.

I HOPE THERE IS A WAY THAT WE CAN WORK TOGETHER TOWARDS A GOAL OF ELIMINATING SEXISM IN ANYWAY THAT IT EMCOMES IN.

I UNDERSTAND HER ARGUMENT.

CAITLYN HAS MADE STATEMENTS THAT SEEM OFF LET'S SAY.

AND HE IS -- SHE IS VERY NEW TO THIS TRANSITION.

SO THERE ARE ISSUES THAT SHE WILL NOT HAVE KNOWN ABOUT THAT SHE WOULD NOT HAVE PERSONAL UNDERSTANDING OF.

AND MAYBE THAT WILL TAKE A LITTLE WHILE FOR HER TO GET ACTUALLYMATION.

AND OVER TIME HOPEFULLY WE WILL BE ABLE TO WORK TOGETHER TO WORK TOWARDS GREATER WOMEN'S INCLUSION.

>> YEAH, I MEAN I CAN UNDERSTAND THIS NOTION THAT IF WE UNDERSTAND GENDER TO BE A SOCIAL CONSTRUCT THEN HOW IS IT THAT WE CAN SORT OF HAVE ALL OF THESE CLAIMS TO HAVING A FEMALE BRAIN WHICH CAITLYN JENNER ESSENTIALLY PUT FORWARD.

THIS IDEA THAT THERE IS A MALE AND FEMALE BRAIN.

WE HAVE BEEN TRYING TO MOVE AWAY FROM THIS AS WOMEN FOR A LONGTIME.

AND I ALSO THINK THERE ARE WAYS THIS UNDERMINES SOME MEN WHO HAVE A SENSE WHERE THEY ARE IN TOUCH WITH THEIR EMOTIONS AND THEN THEY WONDER GOODNESS, DO I MAYBE HAVE SOME OTHER SEXUALITY?

AND IT'S NOT NECESSARILY THAT CAITLYN IS WRONG.

BUT I DO THINK THAT HER COMING OUT SORT OF AS A BEAUTIFUL GLAMOROUS UNBELIEVABLY STEREOTYPED WOMAN IS ALSO SOMEWHAT PROBLEMATIC FOR THE WOMEN'S RIGHTS MOVEMENT EVENTUALLY.

>> IF YOU WERE ADVISING THE HUMAN RIGHTS CAMPAIGN WHICH IS YOU KNOW SPEAKS CERTAINLY HAS THE BIGGEST MICROPHONE AS FAR AS TRANSGENDER RIGHTS ARE CONCERNED HOW WOULD YOU ADVISE THEM TO HAVE TRANSGENDER WOMEN -- BECAUSE THERE ARE TRANSGENERALEDDER MEN BUT MANY MORE TRANSGENDERED WOMEN SPEAKING AS ADVOCATES.

>> IT IS TRICKY.

I WILL TELL YOU ONE OF THE THINGS THAT DID BRING ME TO TEARS AND IF YOU HAVE NOT SEEN IT GOOGLE IT.

DUSTIN HOFFMAN HAD A MOMENT WHERE HE TALKED ABOUT HIS TRANSFORMATION INTO A WOMAN FOR THE ROLE OF TOOTSIE.

IN THAT VIDEO HE REALLY TALKS ABOUT THE FACT THAT HE WAS SURPRISED WHEN THE MAKEUP ARTIST TRANSFORMED HIM INTO A WOMAN HE WAS NOT BEAUTIFUL AND THOUGHT ABOUT WHAT IT MEANT THAT IT REALIZED THAT BEAUTIFUL WOMEN WERE DISMISSED IN OUR SOCIETY AND HE HAD A REVELATION ABOUT WHAT IT WAS REALLY LIKE TO SIT IN A WOMAN'S SHOES WHO DOES HAVE TO COMBAT THIS CONSTANT PRESSURE AROUND HOW WE LOOK.

AND I DON'T KNOW THAT CAITLYN JENNER HAS YET EXPERIENCED THAT.

SHE LOOKS GORGEOUS BY ALL ACCOUNTS.

>> YOUR THOUGHTS?

>> I THINK ACTUALLY I'M MORE SYMPATHETIC TO THE ROLE OF WOMEN THAT TRY TO PRESS FORWARD AND PRESENT WOMEN'S RIGHTS ISSUES.

AND LOOK, I APPLAUD NOT ONLY THE TRANSGENDER MOVEMENT BUT THE CELEBRITY STATUS THAT CAME WITH IT.

ON THE OTHER HAND, I LAMENT THE CELEBRITY STATUS THAT CAME WITH IT.

BECAUSE THERE ARE SO MANY HARD-WORKING WOMEN IN EVERY CONCEIVABLE WAY TRYING TO MAKE DIFFERENCES.

AND THEIR VOICES ARE JUST AS IMPORTANT AS THE CELEBRITY ONES.

>> ABSOLUTELY.

>> IS IT AS VALID TO HEAR A TRANSGENDERED WOMEN CLAIMING TO BE FOR WOMEN'S RIGHTS AND ADVOCATING FOR WOMEN'S RIGHTS AS A BIOLOGICALLY BORN WOMAN?

>> PERSONALLY, I THINK IT'S REALLY IMPORTANT TO HAVE PEOPLE ON BOTH MEN AND WOMEN WHO AGREE WITH THE IMPORTANCE OF CELEBRATING WOMEN AND THAT WE SHOULD BE TREATED EQUALLY IN ALL WAYS.

AND WHETHER THAT PERSON IS TRANSGENDER OR NOT IT'S IMPORTANT THAT WE HAVE ALLIES.

>> ALL RIGHT.

BEHIND THE HEADLINES.

SENATOR CLAIRE McCASKILL, THE MISSOURI DEMOCRAT SAYS SHE IS LADY LIKE AND AMBITIOUS.

>> YOU KNOW, SO FUNNY ONE OF MY COLLEAGUES READ THIS BOOK THE FIRST I GOT BACK THE E-MAIL LIKE TWO DAYS LATER YOU'RE OBVIOUSLY NOT RUNNING FOR PRESIDENT.

BECAUSE I AM PRETTY FORTHCOMING IN THE BOOK ABOUT MY PERSONAL LIFE AND VERY TRANSPARENT ABOUT WHAT I HAVE DONE ALONG THE WAY TO HELP MY CAREER.

>> IN THE BOOK THE SENATOR REVEALS THE STRATEGY BEHIND HER SUCCESSFUL 2012 BID FOR REELECTION.

THE PLAN TO HAND PICK HER OPPONENT HAS BEEN PRAISED AND CRITICIZED.

>> I KNEW THAT TODD AKIN WOULD BE THE RIGHT CANDIDATE BECAUSE HE WAS A PRINCIPLED MAN THAT HAD BELIEFS THAT I THOUGHT WERE OUT OF THE MAINSTREAM AND HE DID NOT HAVE ENOUGH MONEY SO I CUT AN AD THAT SAID THIS IS CLAIRE, I APPROVE THIS MESSAGE TODD AKIN IS TOO CONSERVATIVE FOR MISSOURI WHICH WAS TRUE AND I LISTED THE REASONS HE WAS TOO CONSERVATIVE.

AND THE REASONS I LISTED WERE WHAT VOTERS LIKED.

WE SPENT MORE MONEY ON HIM THAN HE SPENT IN HIS PRIMARY ELECTION.

>> THEN CONTROVERSIAL COMMENTS BY AKIN DURING THE ELECTION WENT VIRAL.

>> IF IT IS A LEGITIMATE RAPE THE FEMALE BODY HAS WAYS TO SHUT THAT DOWN.

>> WE KNEW HE WOULD SAY THINGS THAT WOULD BE OFF KILOMETRE IN TERMS OF APPEALING TO THE VOTERS.

WE HAD NO IDEA HE WOULD SAY SOMETHING THAT OUTRAGEOUS.

IT MADE MY CAMPAIGN EASIER.

>> STRANGE AND TENACITY HAVE BEEN THE HALLMARKS OF HER SUCCESS.

SHE LEARNED IN HIGH SCHOOL WHEN SHE SET HER SIGHTS ON HOMECOMING QUEEN AFTER LOSING A SPOT ON THE CLEAR LEADING SQUAD.

>> THE HOME QUEENING QUEEN WAS THE GIRLFRIEND OF THE QUARTERBACK.

AND I FIGURED OUT THE CONSTITUENCY WAS THE FOOTBALL TEAM.

AND THEY ARE THE ONES WHO VOTED.

WELL THERE ARE MORE LINEMEN THAN QUARTERBACKS AND IT WAS A MATTER OF COUNTING VOTES.

SO I REACHED OUT TO ALL THE LINEMEN AND MADE FRIENDS AND FIXED THEM UP WITH DATES AND I GOT ELECTED HOMECOMING QUEEN.

IT WAS A SUCCESSFULLY EXECUTED STRATEGY FOR SOMETHING LOOKING BACK SEEMED SILLY.

>> EMBARRASSING TO TELL BUT SHE HAD REASONS FOR INCLUDING IT IN THE BOOK.

>> WHAT I'M TRYING TO DO IS MAKE YOUNG WOMEN OWN THEIR AMBITION AND REALIZE THAT STRATEGY IS REALLY AN IMPORTANT PART OF GRABBING YOUR DREAM.

>> MISS CASS KILL CREDITS HER PARENTS FOR HER DRIVE ESPECIALLY HER FATHER WHO TOLD HER SHE COULD BE MORE AND ACCOMPLISH MORE THAN SOCIETY EXPECTED.

HER MOTHER WAS POLITICALLY ACTIVE AND A FEMINIST BUT McCASKILL DID NOT ALWAYS APPRECIATE HER MOTHER AS A ROLE MODEL.

>> I WAS MORTIFIED WHEN SHE GOT ELECTED TO THE CITY COUNCIL BECAUSE SHE WAS SO OUTSPOKEN AND OPINIONATED A YOUNG TEENAGER I WANTED TO CRAWL IN A HOLE AND I DON'T KNOW HER.

>> SHE WAS DRAWN TO POLITICS AND IN 1982, RAN FOR AND WON A SEAT IN THE MISSOURI HOUSE OF REPRESENTATIVES.

>> IT WAS HARD AND I'M NOT SURE I DID IT RIGHT.

I'M NOT SAYING I WAS RIGHT IN THE WAY I HANDLED IT.

I WAS SINGLE IN MY 20s.

AND IT WAS AN INCREDIBLY MALE-DOMINATED PLACE.

AND A LOT OF INAPPROPRIATE BEHAVIOR.

A LOT OF SEXISM.

I WAS CALLED A WHORE.

THE SPEAKER OF THE HOUSE WHEN I ASKED HIM HOW TO GET MY BILL OUT OF COMMITTEE AND HE ASKED ME IF I BROUGHT MY KNEE PADS.

AND HE LAUGHED AND THOUGHT IT WAS A FUNNY JOKE.

I KIND OF LAUGHED.

HA, HA, BUT I NEVER FORGOT IT AND IT FOCUSED ME.

I THINK I HYPER FOCUSED ON DOING WELL PARTIALLY BECAUSE OF WHAT I WAS ENCOUNTERING.

NOW, MAYBE I SHOULD HAVE CONFRONTED IT.

MAYBE I SHOULD HAVE BEEN MORE FRONTALLY OFFENDED AND SAID WAIT.

BUT I DIDN'T.

I JUST USE TO DO AS A MOTIVATION TO WORK HARDER AND SMARTER TO ELEVATE MYSELF BEYOND THE POSITIONS THAT ALL THE GUYS WERE IN AND IT WORKED FOR ME.

NOW, I WOULD NOT -- I AM AHE NOT SURE I WOULD TELL MY DAUGHTERS TO INTERNALIZE LIKE THAT.

TODAY, IT'S IMPORTANT THAT WE CALL OUT THAT BEHAVIOR IN THE WORKPLACE.

BUT AT THE TIME I WAS TRYING TO BE POLITICALLY EFFECTIVE AND I WAS WORRIED THAT IF I WAS TOO CONFRONTATIONAL IT WOULD SET ME BACK.

>> IN 2008 SHE TOOK A CONTROVERSIAL AND POLITICALLY RISKY STAND SHE BACKED BARACK OBAMA AND NOT HILLARY CLINTON.

McCASKILL SAYS A YOUNG AND TRUSTED ADVISER CONVINCED HER TO MAKE THAT MOVE.

>> MY DAUGHTER GOT IN MY FACE AND SAID MOM, FOR YEARS YOU'VE BEEN TELLING US THE REASON YOU'VE HAD TO MISS THINGS IN OUR LIFE WAS BECAUSE YOU WERE MAKING A DIFFERENCE.

AND YOU WERE DOING THINGS THAT WERE IMPORTANT.

HOW DO YOU LOOK YOURSELF IN THE MIRROR RIGHT NOW?

THE ONLY REASON YOU ARE NOT ENDORSING BARACK OBAMA IS BECAUSE YOU ARE WORRIED ABOUT YOUR POLITICAL SKIN.

AND SHE WAS RIGHT.

I WAS WORRIED ABOUT THE POLITICAL IMPACT ON ME.

NOT ABOUT WHAT WAS RIGHT TO DO FOR THE COUNTRY AND SO THE NEXT CALL I CALLED AND SAID I'M IN.

>> McCASKILL WANTS TO SERVE ONE MORE TERM IN THE SENATE THAT COULD BE MORE EFFECTIVE IF THERE WERE MORE WOMEN IN IT.

>> I HAVE REPUBLICAN WOMEN COLLEAGUES THAT I DISAGREE WITH ON A HOST OF ISSUES.

BUT WE DON'T THROW EACH OTHER UNDER THE BUS AND DON'T TRY TO SCORE POINTS AT EACH OTHER'S EXPENSE.

IF WE COULD GET TO 60 WE WOULD HAVE A MUCH MORE FUNCTIONAL GOVERNMENT.

I DO BELIEVE THAT.

>> SO, GIRLS ARE USED TO BEING TOLD TO BE AMBITIOUS BUT WHAT ABOUT STRATEGIC?

>> I COULD NOT AGREE WITH HER MESSAGE MOREMENT IT'S ABSOLUTELY CRITICAL.

THE REALITY IS EVERYONE IN THE WORLD ESPECIALLY THE PROFESSIONAL WORLD ACTS STRATEGICALLY.

AND IF YOU DO NOT UNDERSTAND STRATEGY THEN YOU ARE PUTTING YOURSELF SORT OF AT THEIR MERCY.

AND I WILL TELL YOU I TEACH AN ADVANCED CLASS ON STRATEGY AND NEGOTIATIONS IN OUR SCHOOL OF POLITICAL MANAGEMENT.

AND I IMMEDIATELY HAVE EVERYONE READ WILLIAM REICHER'S THE ART OF POLITICAL MANIPULATION AND THE PRINCE.

BECAUSE IT IS THE FIRST STEPS TO REALLY UNDERSTANDING HOW TO CHART A COURSE TO ACHIEVE YOUR AIM.

>> YOUR THOUGHTS ABOUT ESPECIALLY HELPING IN A WAY TO SELECT HER OPPONENT?

WHICH IS NOT USUALLY DONE?

IS THAT TOO STRATEGIC OR GOOD IDEA?

>> IT IS A LITTLE BIT TOO STRATEGIC.

I THINK IT'S IMPORTANT FOR US TO WHATEVER YOU ARE GOING AFTER THAT YOU HAVE INTEGRITY ABOUT WHAT YOU ARE DOING.

>> BUT THERE WAS NOT -- SHE WAS NOT UNDER HANDED ABOUT THIS IN ANYWAY.

BUT SHE -- I MEAN I AM TROUBLED WITH THERE WAS NO INTEGRITY.

IT WAS JUST OUT OF THE BOX.

>> SHE WAS BOLD.

>> SHE IS VERY BOLD.

>> IT SHOWED STRENGTH.

IT SHOWED SHE WAS ALMOST IN CHARGE OF THE SITUATION AND WOMEN ARE RARELY PORTRAYED IN THAT ROLE.

LOOK I WILL BE PART OF THE DECISION MAKING PROCESS AND I COULD NOT AGREE MORE ABOUT OWN YOUR AMBITION AND STRATEGY BECAUSE MEN HAVE KNOWN THAT FOR YEARS IN ALL THE TEAM SPORTS THAT WHERE THEY START BUILDING THEIR NETWORKS.

AND IT'S BEEN HARD FOR WOMEN TO BUILD NETWORKS.

IT'S TAKEN US DECADES WHEN SHE TALKS ABOUT THE RESPONSES THAT SHE GOT AS A YOUNG GIRL.

THAT SEEMS HORRIFYING NOW BUT FOR US IT WAS NORMAL.

SO BRAVO FOR HER FOR BEING SO TRANSPARENT.

>> AND WHAT ABOUT CALLING PEOPLE SHE SUGGESTS YOUNG WOMEN CALL OUT MEN ON SEXISM LIKE THE NAME IT CHANGE IT CAMPAIGN.

>> YOU HAVE TO DO THAT.

WE ARE IN A TIME TODAY WHERE YOU HAVE THE LEGAL BACKING BEHIND YOU TO DO THAT.

AND THERE'S NO REASON FOR YOU TO PUT UP WITH THAT BEHAVIOR IN ANYWAY SHAPE OR FORM TO ADVANCE YOUR CAREER.

BUT I AGREE ALSO IN THE FACT THAT THERE NEEDS TO BE MORE WOMEN IN THE SENATE AND SPECIFICALLY MORE WOMEN OF COLOR IN THE SENATE.

IT'S BEEN 17 YEARS SINCE WE HAVE HAD A BLACK WOMAN IN THE SENATE AND ONE IN THE HISTORY.

SO I WANT TO DIVERSIFY EVEN THE WOMEN.

>> IT'S GOING TO BE DIFFICULT.

I THINK MILLENNIAL WOMEN DO NOT SEE GOVERNMENT AS A WAY TO SUCCESS AND WE ARE NOT RUNNING TO THE PUBLIC SECTOR WE SEE A LACK OF A LOT OF THINGS.

BUT WHEN WE SEE GOOD EXAMPLES OF WOMEN IN POWER BREAKING STEREOTYPES IT SAYS OK MAYBE WE WILL TAKE A SECOND LOOK AT PUBLIC LIFE.

>> I HOPE MORE OF YOU DECIDE TO GET INTO THE PUBLIC SECTOR.

FOLLOW ME ON TWITTER AND FOLLOW OUR WEBSITE PBS.ORG/TOTHECONTRARY.

AND WHETHER YOU AGREE OR THINK TO THE CONTRARY SEE YOU NEXT WEEK.

[♪♪♪] FOR A TRANSCRIPT OR TO SEE AN ON-LINE VERSION OF THIS EPISODE OF TO THE CONTRARY VISIT OUR WEBSITE AT PBS.ORG/TOTHECONTRARY.

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