He has a hobbit’s chance.

David Zuckerman, that is. Having won the Democratic gubernatorial primary, he now faces an epic adventure in his attempt to defeat Gov. Phil Smau– I mean, Scott.

If the election were held today, Scott would win in a walk. But there is a path to victory for our friend the Zuckerhobbit. Not gonna be easy, though. And quite a few factors are largely out of his control.

As I get to play the role of J.R.R. Tolkien, here’s the long and winding road to a Zuckerman victory.

First, he needs a bunch of money right quick. Zuckerman’s campaign entered the month of August with a cash balance of $42,000. He also had a $26,000 surplus from previous campaigns. At the end of July, he reported several mass media buys totaling $15,000 that weren’t included in his August 1 financial report. I conclude that his actual cash balance on 8/1 was $27,000. Add in the surplus, and you’ve got $53,000.

To be competitive in a statewide race for governor, you need to have — conservatively — at least a million bucks. Preferably a million and a half. Between the launch of his candidacy and the end of July, Zuckerman raised $347,000. In the 2016 cycle, which had some different deadlines, Dem nominee Sue Minter had raised over a million bucks by mid-August. He has to pick up the pace at a time when liberal donors have plenty of calls for their money, including the race for president, the battle for a U.S. Senate majority, and efforts to turn state legislatures blue in time for the 2022 redistricting wars.

Second, he needs not to wake the dragon. In this case, the Republican Governors Association. So far, the RGA has committed very little money to defending Scott. But that could change in an instant. If the RGA sees evidence of a rising Zuckerman insurgency, it can pour in boatloads of cash in an instant. In 2016, it spent more than $3 million to get Scott into the corner office. It can, and will, do so again if Scott looks vulnerable. Zuckerman has to hope that the dragon doesn’t wake up until late October or thereabouts. Seems unlikely; the RGA is smarter than that.

Third, he needs to nab the Progressive nomination. Perennial candidates Cris Ericson and Boots Wardinski were the only two names on the Prog ballot, but the party asked supporters to consider a write-in vote for Zuckerman. The unofficial totals show Ericson with 254 votes and Wardinski with 239. There were 345 write-in votes; he has to hoe that the bulk of those votes are for him. If Ericson or Wardinski takes the Prog nom, that could drain a precious percentage point or two from Zuckerman’s November total.

Fourth, he needs John Klar to stay in the race. Now that Klar has lost the Republican primary, he’s filed as an independent candidate for governor. I don’t expect Klar to take much of a bite out of Scott’s totals, but every vote counts. In 2014’s gubernatorial nail-biter, Libertarian Dan Feliciano drew 4.4% of the vote while Republican Scott Milne lost to incumbent Dem Peter Shumlin by only 1.3%. If Feliciano hadn’t run and Milne had attracted a modest portion of Feliciano’s support, Mr. Travel would have been our governor.

The preceding two are relatively small items, but important. Now back to bigger stuff.

Fifth, he has to persuade Democrats to vote for him — and actively support him. Many Democrats don’t really mind Phil Scott as governor, and quite a few actively support him. Some have a specific dislike for Zuckerman. A lot of Dems don’t like supporting Progressives, and would prefer a moderate Republican governor to a Progressive. Some are simply daunted by the prospect of beating Scott, and have resigned themselves to waiting until he moves on.

The primary results revealed quite a bit of skepticism about the choices on offer. A full 13% of Democratic voters either left the gubernatorial line blank or cast a write-in — most of those presumably for Scott.

Zuckerman not only needs to win their hearts and minds, he needs to open their wallets and inspire campaign volunteers from party ranks.

Sixth, he needs Molly Gray. This usually works the other way round; Milne, for instance, could use every bit of Phil Scott that he can get. But in this case, Gray has clearly captured the enthusiastic support of the Democratic base. Actively campaigning as a ticket would help Zuckerman more than Gray. In his speech at Thursday’s unity event, he even made an overt reference to campaigning with Gray.

The question is, how does Gray play it? She’d presumably have more influence in a Zuckerman administration than under Scott, especially if she did take an active role in helping Zuckerman win. But if we put on our Machiavellian hats, there are good reasons to stay aloof. She could actually anger some supporters if she goes out of her way for Zuckerman. She’s also universlly expected run for higher office. She couldn’t run for governor against an incumbent Zuckerman, and Gov. Zuckerman could decide to run for the next Congressional vacancy. But if he joins Tim Ashe on the sidelines as a loser, the path is that much clearer for Gray’s political ascendancy.

An obvious corollary to this point: He could use the active support of the Dems’ statewide officeholders, who face no serious threats to re-election and are very popular with the base.

Seventh, he needs to poke holes in Scott’s Teflon. Right now, Scott looks invincible. He has much higher positive ratings among Democrats than among Republicans. His handling of the pandemic has won him widespread praise. It cements his reputation as a thoughful leader willing to buck his party’s line. Zuckerman has to identify attacks that resonate with voters. Trying to label Scott as a pawn of national Republicans won’t stick.

Zuckerman trotted out a potentially effective line in his Thursday speech: Scott is a decent manager, but he’s not a visionary leader. Scott may have shepherded us through the pandemic, but is he the right person to face the many challenges of post-coronavirus Vermont? Especially if he’s clashing with the Democratic Legislature on major policy ideas?

Eighth, he needs some stuff to go badly between now and November. Machiavelli hat again. Scott is respected for his handling of Covid-19 so far, but what if things get worse in the fall? What if restaurants, small retailers and tourism businesses start falling like autumn leaves? What if school reopening is a mess? What if Covid finally hits us with full force? If those things start happening, voters may turn against the governor. There’s still time.

Ninth, he needs a strong, simple sales pitch. Scott’s political success has been based on a few ideas repeated endlessly. Zuckerman needs the same. And his pitch needs to appeal to his Progressive base and to Democrats and centrists who are skeptical about Progressive politics.

He can’t just reel off a wish list of paid leave, higher wages, universal broadband, rural development, expanded health care, infrastructure investment, etc., etc. He has to make it seem practical. He might be able to win over voters, or enough of them anyway, with his idea for a temporary wealth tax. He’ll have to show how it would work, how much money it would generate, and how he’d pay for his proposals without raising everyone’s taxes.

I think that’s about all. Quite the list, n’est-ce pas? But it’s not impossible — just highly unlikely. I wish the Zuckerhobbit well on his quest.