05/06/2008 04:35 pm ET Updated May 25, 2011

How to Lose an Election 101

A couple of years ago I listened as one Democratic
activist described what it felt like to be a Democrat
during most of the Bush-pushing last decade. She said
it was akin to being on a football field and watching
as the opposing team unveiled one Adonis after the
other as you sat with a bench full of misfits. In
other words, it was like having the first half of "Bad
News Bears" on a constant loop -- only without the
laughs. (Yes I know the "Bad News Bears" is about
baseball not football but you get my point).

Everything was supposed to be different this election.
After all, a quick glance at the lineup on the GOP
side -- Rudy Giuliani, John McCain, not to mention Ron
Paul, made it pretty clear that this was certainly not
a bench full of Adonis types. (Although Mitt Romney
and his Ken doll looks and matching family did seem
straight out of central casting. Unfortunately his
election year makeover into a real Republican made
John Kerry's flip-flopping look like child's play).
Months ago I was sitting in a greenroom preparing to
do an interview when a GOP strategist lamented about
the sad state of John McCain's campaign. Not only had
he been reduced to carrying his own luggage -- serving as
his own one-man-band-advance team -- he had allegedly
arrived late at an important event because his
transportation had broken down and he had to find his
own way there without the ubiquitous team of handlers,
a luxury his tattered campaign could not afford.

Meanwhile the Democrats for once had an all-star
lineup. Or so it seemed.

So how did it all come to this, with Democrats
preparing to battle all the way to the convention, and
to ultimately grant the GOP another four years in 1600
Pennsylvania Avenue? Below, a look at the top 10
people and moments that are helping the Democrats
return to the glory days of loserdom:

10. Howard Dean. You've heard the saying "the fish
rots from the head." Well the head of the Democratic
National Committee is Howard Dean. From his inability
to reign in state leaders when setting the primary
calendar, to his inability to effectively moderate and
resolve the Florida, Michigan mess, Dean has proven
himself to be a likable leader but not necessarily a
strong one. Just as a parent has to know that
sometimes you spoil and other times you spank, it
doesn't appear that Dean has mastered the good cop/bad
cop routine. As a result the kids have taken over.

9. The South Carolina Debate. Have you ever been at
dinner with a couple that seemed perfectly normal
until a slight disagreement erupts into an all out
verbal slugfest in which they start airing each
other's dirty laundry? Like about the time one of them
cheated on the other while they were both in grad
school? Well watching this debate was almost as
uncomfortable. From Wal-Mart to Rezko it was as though
the Democrats were determined to give the GOP
opposition-research team as much helpful info. as
possible. Mission accomplished! And the tone of the
campaign? Well it's all been downhill since then.

8. Saturday Night Live. Let me start by saying that
I am a fan of "Saturday Night Live." It's funny.
That's because it's this thing called a comedy.
Comedies are meant to make people laugh not to serve
as an instruction manual for how to run a presidential
election. But for some reason some members of the
media (and certain campaigns) have decided to
reference SNL as if it were a journalism class taught
by the ghost of Edward R. Murrow. While we may be
laughing with them (and they continue to laugh all the
way to the bank) there is no doubt that the SNL crew
has helped reshape the coverage of the campaign (72
straight hours of Rev. Wright coverage anyone? After
all we wouldn't want that Obama to have it too easy)
and thereby they have reshaped the narrative of this
campaign as well.

7. Bittergate. There's a lot of blame to go around for
this one. You can question the motives of alleged
Obama supporter Mayhill Fowler for recording the
comments in the first place. You can question what
Obama -- Mr. Oratory -- was thinking for putting the remarks
together so clumsily. You can also question the
Clinton camp's efforts to capitalize on a comment that
while un-P.C. -- was essentially true. When I first heard
the remarks I was immediately reminded of a scene from
the TV show I'll Fly Away, which was set in the
South in the 1960s. A poor white teen from the "wrong
side of the tracks," told his wealthier white friend
that his skin color remained the one thing that
allowed him to maintain some measure of status in
society, regardless of what side of the tracks he
lived on. As a result, he was not exactly psyched
about civil rights. Yes we've come a long way since
those days, but for a few, that reality holds some
truth. The sad thing about "bittergate" is that we
were all so busy trying to assess the political
fallout that we didn't really tackle much of the
substance behind the remarks.

6. Marc Penn. Marc Penn. Marc Penn. This one is
pretty self-explanatory but please allow me a couple
of quick thoughts. Hillary actually has (gasp!) a
personality. One that smiles and laughs, and yes,
occasionally cries. But with svengali Penn at the
strategic helm of her campaign who would have known
it? His extreme focus on numbers (and getting himself
on TV) seemed to suck what early life there was in her
frontrunner campaign, out of it. Is it a coincidence
that since throwing him overboard the S.S. Hillary
seems to be running a lot more smoothly?

5. The Edwards Campaign, R.I.P. 1/30/08. After years
of reminding us to never forget the nation's working
poor, John Edwards became the butt of countless late
night jokes, all because of one ill-advised,
overpriced haircut. But guess who's having the last
laugh now. Watching Obama bowl and Hillary drink beer
in Pennsylvania, one couldn't help note the irony that
after Democrats kicked the one true, good ol' boy
candidate to the curb, they then decided that the good
'ol boy vote was the most prized possession of the
election. And the economy -- particularly its impact on
the working class -- is not just an important issue this
election but the deciding issue. Looks like the son of
a millworker was on to something when he spoke of
those "Two Americas."

4. Rev. Jeremiah Wright. So much to say, and yet I am
hesitant to give this guy any more ink than he's
already gotten. Yes the media fed into to his story
(myself included). Yes the media is partially to
blame. But there's a saying: Just because someone
gives you the gun doesn't mean you have to pull the
trigger. Rev. Wright just doesn't know when to put
away the ammo.

3. Bill Clinton. Having been raised as a child in the
cult of Clinton (one parent is a full-fledged fanatic)
it was a bit of shock to see the laid-back Bubba (aka
first-black president) that I remember watching as a
kid blow his sax on The Arsenio Hall Show, replaced
by some grumpy guy who runs around making un-P.C.
analogies between black candidates who don't really
have much in common. As the most brilliant political
mind of the last century (or at least one of them) he
knows that the ongoing bloodbath between his wife and
Obama is ripping the Democratic Party apart, and
possibly his legacy as well. But overcome by his
lifelong overachiever streak he's been rendered
helpless by his desire to win, and his yearning to
give us all the presidency that he thinks Ken Starr
shortchanged us on last time. Honestly, can you blame

2. Florida and Michigan. It's hard to believe that the
states responsible for bringing so much joy in the
forms of Motown and Mickey Mouse could also be
responsible for such a reign of terror. The "will they
or won't they" be seated at the convention question
has turned older, faster than any of the "will they or
won't they" romantic entanglements on a long-running
sitcom (think Ross and Rachel on Friends or William
and Joan on Girlfriends.) We get it. It's the not
the fault of the citizens of these states that their
knuckleheaded elected officials put them in this
position by ignoring the DNC's mandate. Here's a
suggestion. How about an old-fashioned game of rock,
paper, scissors to decide this mess? Or maybe Howard
Dean can make everyone draw straws? Anything to just
put us all out of our misery already. I know this
much. When this election is finally over the last
place I'm going is Disney World.

1. Superdelegates. Raise your hand if you actually
knew what a superdelegate was 18 months ago. Now raise
your hand if you now wish that you had never heard of
them and that they didn't exist. Regardless of how
this primary ultimately turns out the reality is that
what started out as a minor party battle could have
been prevented from turning into an all out war were
it not for this cadre of super-wussies. Operating as
some sort of political Opus Dei, they are ready,
willing and able to serve if their party needs
them -- needs them to overturn the will of the people
that is. Democrats always get defensive when they are
labeled as know-it-all elitists. So to disprove this
stereotype they have helpfully put together a team of
hundreds of party "insiders" who will correct the
nominating process should the idiotic masses get it
wrong. There's nothing like watching a bunch of
political types pick a presidential candidate based on
their own personal career ambitions to restore one's
faith in democracy.

Let the kamikaze campaign continue. Onward and

P.S. I'm sure I missed a few so please feel free to
post your own nominees for the list in the comments