Can't do it with a POD of 1998, but I figure that I'll do something a little unorthodox, anyway.
Elizabeth Hanford worked for the Kennedy-Johnson ticket in 1960, and began working for President Lyndon Johnson near the end of his term. In 1969, she stayed on when Hubert Humphrey defeated Richard Nixon for the Presidency, serving as Deputy Assistant to President Humphrey for Consumer Affairs. In 1973, Humphrey appointed her to a seven-year term on the Federal Trade Commission.
In 1975, Hanford met Senator Joe Biden for the first time. The two hit it off and married in 1977, prior to the end of Elizabeth's term on the FTC in 1979.
She served as director of the White House Office of Public Liaison from 1981 to 1983 and as United States Secretary of Transportation from 1983 to 1987 under President Scoop Jackson. She was also appointed by Jackson to chair taskforces that sought to reform federal and state laws to ensure equal rights for women. She was the first woman appointed Secretary of Transportation. In this role, she was the first woman to have served as the head of a branch of the United States Military, as the United States Coast Guard was under the Department of Transportation at the time. Biden's appointment was "particularly irritating" to conservative activists, since "[she was] viewed by the right as [an] aggressive feminist."
Biden served as United States Secretary of Labor from 1989 to 1990 under President Jeane Kirkpatrick; she is the first woman to serve in two different Cabinet positions in the administrations of two Presidents.
Biden's husband Joe Biden was Democratic nominee in the US presidential election of 1996. Elizabeth Hanford Biden, who would have become First Lady had her husband won the election, received recognition for her speech at the 1996 Democratic National Convention, during which she walked out into the audience while talking conversationally about her husband's qualities.
Her husband, acting as Senate Majority Leader concurrent with his time as a Presidential nominee, suffered a stroke in 1997 that ultimately led to his death in 1998. The Governor of Delaware appointed Biden to his position, and she subsequently won election to a full term to replace her husband that November.
In 2000, Biden declared herself a candidate for President of the United States. She ultimately won out over a field divided between the party's progressives (who supported Paul Wellstone), and the party's conservatives (who supported Joe Lieberman). Biden chose as her running mate Senator Rudy Giuliani of New York and defeated Vice President Jack Danforth for the White House in a close election.