Debate Preview: Why My Money’s on Jim Webb

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Carl “The Dig” Diggler has covered national politics for 30 years, and is the author of “Think-ocracy: The Rise Of The Brainy Congressman”. He currently resides in New York, but also spends time in Washington DC and Los Angeles (but most of all, airports!). Diggler got his start in journalism as the chief political editor for the Minnetonka Bugle.

It’s showtime! All five candidates for the Democratic Presidential nomination will finally be on stage together tonight in the elegant Wynn Resort and Casino in Las Vegas. The candidates are under a lot of pressure to prove they’re ready for primetime. One thing’s for sure: what happens in Vegas… will be fodder for my weekly e-chat!

Herewith are The Dig’s recommendations for what the candidates have to do tonight:

Sen. Jim Webb – As a veteran, Reagan administration alum, full professor at Naval college, and hardcore moderate, it’s obvious that Jim Webb is Hillary’s main competition for the nomination in all but name only. Webb is liable to have his big breakout moment at the debate when Democratic voters get a look at his square jaw, burly muscles, and big heavy combat boots. Adding to his long list of positives, the former Virginia Senator has a wife from another country, something very popular with Millennials. Furthermore, his habit of carrying a gun in this age of mass shootings could lead him to personally stopping a spree killer in the act, a moment that would almost certainly go viral.

The only knock on Webb? He might be too perfect a candidate.

If Webb brings the heat tonight, voters may feel like they’re not good enough for the maverick legislator and award-winning novelist. When he talks, the man commands love, respect, and fear. He has the gleam of Ronald Reagan in a Democrat’s youthful body. Some voters may fear such a perfect specimen of masculinity. I don’t. I’m not afraid to love and lose and be hurt again. But will it play with Latino voters in Iowa?

Gov. Lincoln Chafee – If there’s one impediment to Senator Webb’s path to the nomination, it’s former Rhode Island Governor (and Senator!) Lincoln Chafee. Chafee is the embodiment of the radical centrism and compromise Democratic voters are craving right now: a former Republican-turned-Independent-turned-Democrat in the Mike Bloomberg mold who’s just as comfortable debating John McCain in the Senate cloakroom as he is rocking out to Imagine Dragons at the Newport Folk Festival. The Linc needs to bring his effortless No Labels cool to the debate stage if he wants to wow those Millennials who are so over partisanship and just in the market for practical solutions.

Sen. Bernie Sanders – After surging all summer, the Sanders bubble has finally plateaued. It’s clear the bombastic Vermont Senator’s extreme-left policies of taxing the rich and throwing away free education have reached the limit of their appeal. Now that we’re past Labor Day, silly season is over and in order to stay relevant Sanders will need to ditch Democratic Socialism and present practical policies that will appeal to voters, like reforming the carried interest tax deduction and means-testing Medicare. One thing’s for certain, and two things for sure: pet issues don’t carry you past Iowa, and hair is meant to be combed.

Sec. Hillary Clinton – With the former Secretary of State having led in every poll from here to the Mesolithic Era, this race is Hillary’s to lose. She needs to stay the course, ignore her rivals, and keep connecting directly with her core audience. No other candidate has her kind of social media savvy, and she would do well to use it on stage. A well-timed selfie photograph or meme picture during the debate could be a huge “Web 2.0” moment for this veteran politico. On the other hand, Hillary’s famous love of tech has gotten her embroiled in an email scandal that’s been dominating headlines and giving her lawyers agita. One thing’s for sure: she won’t be “retweeting” a subpoena!

Vice President Joe Biden – Although Joe Biden is still working on his Hamlet impression (“to be or not to be… a candidate!”), according to the rules there’s still time for him to catch Air Force 2 to Las Vegas and grab a podium at the debate. But to win the nomination, he needs to overcome the flake factor and prove his campaign is more than the swansong of an aging politico. If he choses to rise to the occasion here and surprise the political establishment with a Hail Mary right after kickoff, Biden can turn the debate into his personal coming-out party by addressing the two-ton gorilla in the room: the death of his beloved son Beau, who died of brain cancer four months ago.

Biden doesn’t have an Internet following like Sanders’ or a donor base like Clinton’s, but these candidates would have to work twice as hard to have half the tragic personal story — and authentic narrative — he has.

Gov. Martin O’Malley – With a another Mid-Atlantian in the race threatening to suck up what little oxygen remains for him, O’Malley will need to go big if he doesn’t want to go home with sloppy seconds. O’Malley has to hit hard at the Vice President in a way that doesn’t put him in opposition to Obama, who remains a popular figure among Democrats. If Biden predicates his campaign on fulfilling the dying wish of his firstborn son, O’Malley can pull the rug out from under the Veep by poking holes at his son’s record as Attorney-General of Delaware. By landing some solid punches on Joe Biden and his family, O’Malley will be able to thump his chest and say I’m not giving up DelMarVa so easily, Mr. Vice President!

CNN’s moderators Anderson Cooper and Don Lemon – Anderson is a class-act, a sensitive sort you could trust to keep his mitts off your close family members. And while Lemon has a bit of a “street” edge to him, he seems like the kind of guy you could kick back and watch a basketball game with. Chief DC correspondent Jake Tapper is the big loser tonight — about all he can enjoy moderating tonight is the remote control!

Stay tuned tomorrow for exclusive post-debate analysis from “The Dig.” Meanwhile, get your popcorn ready, because the debate starts at 9 PM Eastern on CNN.