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There were a number of reasons that Lieberman was picked as Gore's running mate in 2000. I think the main reasons were #4 -#7 , but I've ordered them this way to make the politics of the time clearer for those who were too young or really not paying attention.
1.) By the time Gore began his campaign, Clinton had been the subject of six years of bogus Clinton-gate scandals (drummed up by both the GOP Congress and the media). The word "Clintonesque" was coined and in wide usage, meaning "lying in a particularly sleazy way". Clinton was already an object of public ridicule when the Monica Lewinsky scandal broke (if you don't believe me, watch almost any television from 1996-2000 to see Clinton caricatured as a lying, selfish, promiscuous red neck).
After Clinton was caught lying under oath about his extra marital affair with Lewinsky, zealots in the House began impeachment proceedings. If Gore had been a different person, he would have worked behind the scenes to get Clinton impeached, so that he could run as the sitting President in 2000 - - a position which would have virtually guaranteed victory. Instead, Gore stood up for Clinton, and denounced the attempted impeachment. But almost every Democrat in Congress chose a different path - - most said Clinton should be censured for lying under oath and some even supported impeachment. Lieberman was one of many who objected to Clinton's actions, and the media focused enough attention on him that he was thrust into the national spotlight for the first time. (IMNSHO, I think the media focused on Lieberman only because he was Jewish; since Jews have traditionally backed Democrats, a Jew objecting to Clinton's actions had "a hook".)
Gore began his formal campaign one month after the attempted impeachment ended; at that time he was polling 20 points behind "any Republican". Clinton continued to be an albatross all through the 2000 campaign - - every time Clinton publicly spoke about the campaign, Gore's poll numbers took a dive. Karl Rove's strategy throughout the campaign was to "have people think 'Clinton' whenever they see 'Gore'" (like having Smirk say over and over that he would "restore honor and dignity to the White House").
Prior to the impeachment, the public perceived Gore as the ultimate family man - - one of the reasons that he was picked for Clinton's running mate is that he was free of sexual scandals and was unlikely to ever be caught in one. But the perfect storm around the impeachment did make the public "think 'Clinton' every time they saw 'Gore'". Picking Lieberman was a way to publicly signal (as Dave Letterman said in late October 2000) Gore "won't be chasing any interns".
2.) Lieberman was and still is popular with moderates and conservatives. Smirk ran in 2000 as a moderate Republican - - picking Lieberman was a way to court moderates and conservatives away from Smirk.
3.) In 2000, the party was deeply divided. The conventional wisdom was that Gore was going to lose in a landslide, due to the fallout from the impeachment attempt. The Left saw the 2000 election as an opportunity to wrestle control of the party away from the Clinton centrists - - and wanted to use Gore's landslide loss to prove that the party needed to move to the left. The centrists in the establishment (including Clinton) were also convinced that Gore would lose in a landslide and wanted to use Gore's landslide loss to prove that the party needed to move farther to the right. Both sides were vocal during the campaign, complaining about everything Gore did, but the centrists had more power and got more air time. Picking Lieberman - - then chair of the DLC - - was a way to court the centrists and party elite.
4.) The 2000 Congress was going to be dominated by Republicans and moderate Democrats. Lieberman was and is somebody who worked well with both groups and would have been a huge asset getting Gore's agenda heard and passed in Congress.
5.) Gore and Lieberman were good friends at the time, something that Gore felt was very important, since they were going to have to work together for (probably) eight years. (This has since changed.)
6.) Picking a Jewish running mate was a strong statement about Gore's commitment to civil rights.
7.) Gore genuinely values opinions that differ from his own. He didn't want a "yes man" for his VP.
8.) Picking Lieberman was one of the few things that Gore did during the campaign which the media approved of.
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