Giuliani could be the most surprising candidate in the young race to challenge Cuomo and another Democratic nominee in 2022. Giuliani is almost certain to have the most well-known name in the field. What's your old man doing? This question was asked by a stranger at the fair. It is not something Zeldin receives with regularity.All evidence indicates that he is putting his energy into his campaign, not just resting on his family's name as many in New York's political circles believed he would when he launched his campaign this spring. He was a Trump adviser for four years and, by one measure the president's most frequent golf buddy. His only run for office was a brief flirtation in New York City with a mayoral campaign.He is now a regular visitor to upstate New York at events such as the Lowville fair, which attracts 3,500 people. Lowville is about halfway between Utica, Canada, and Utica.Giuliani stated that while this may seem impossible, it does not mean we don't try to reach our goal of meeting as many New Yorkers as possible. "Certainly as many 9 million voters as possible and as many registered Republicans (2.9 million) as possible to win this primary."He said that's why we attend the Lewis County Fair. This is why we went to the Greene County Fair. You should go to Nascar. This is why we did the Empire Farm Days.Bill Mahoney/POLITICOGiulianis' first appearance in New York politics was when he was 7 years old. He took the mayoral office oath with his father, a scene-stealing performance which earned him a Saturday Night Live portrayal by Chris Farley. Giulianis, now 35, has pursued a career as a golfer and a job at the White House. His portfolio also included Trump's interaction with sports teams.Many people who saw Giuliani campaigning believe that his efforts should not to be discounted.According to Jeff Graham, who was the former mayor for Watertown, which is located five miles from Lake Ontario, he seems to have more appeal to Trump-oriented voters than Zeldin. Graham hosted Giuliani recently on his local talk radio station.Zeldin hasn't had a lot of success so far. Cuomo is a street fighter so you must be a fighter to compete against him. Graham stated that he will throw a lot more elbows under the basket. Giuliani is more optimistic than I have seen in the other candidates.Giuliani is aware that I support Lee Zeldin," said Assemblyman Chris Tague (the GOP chair in rural Schoharie County west of Albany).Tague said that Giuliani is smart and very good at his feet. He's also very approachable. He was very impressive to me. He is a very knowledgeable person, which impressed me as well. I don't think it is fair to ignore him.In a straw poll of GOP officials conducted in June, Tague supported Zeldin. The Long Island congressman, 41 years old, received 85 percent of the weighted votes. Former Westchester County Executive Rob Astorino received 5 percent. None of the other candidates received support.If the results are similar at the winter party leaders' meeting, Zeldin will be eligible to run for the June primary. He will also be able to identify himself as the party's endorsed candidate to donors and voters. Everyone else will have to focus their efforts on collecting thousands of petition signatures to be eligible to appear on the primary ballot.It is clearly more difficult to win a primary for gubernatorial without the backing of a party. It has been done before. Most recently, Rick Lazio, who served four terms as Congressman representing Long Island, was shocked by Carl Paladino. Paladino is a Buffalo developer who ran an grassroots campaign appealing specifically to voters who would ultimately form Trump's coalition.Another recent example is of a candidate winning major office without any establishment support.Giuliani stated that Trump would have announced his candidacy for president in 2015. This is a good indication of where we were for a gubernatorial election, which was 15-and-a half months away. Some things have moved quickly at this point but I believe if we continue building the grassroots by going to these huge gathering places, we will have a great opportunity.Giuliani promises to bring something that is similar to a Trumpian style to office if elected. New York politics has had a long-standing rule that governors shouldn't publicly clash with state legislators. Those who violate this rule have been punished.In 2007, Eliot Spitzer broke the law by attacking Assembly members who did not support his plan to choose a new state comptroller. He was never able stabilize his administration's relationship with the Legislature. Cuomo slammed Ron Kim, an Assemblyman who had criticised the administration's decision not to disclose the number of Covid-19-related deaths, and he created a national media cycle that focused on the governor's bullying history behind closed doors. This quickly evolved into a discussion about even more inappropriate behavior by Cuomo.Giuliani's campaign pitch includes direct combatting members of the Democratic-dominated Legislature.He said that he would like to invite every Assembly member for lunch in the first 90 days. We will see if there is a chance of building a rapport. If this fails, we should make sure we have the governor's bully pulpit available to reduce taxes.He stated that he would go to the districts of individual legislators to push his agenda, if they refused to follow him aggressively for New York governor.He said that we were going to go above them and reach out to their constituents.Like Giuliani and Zeldin, Zeldin has been a prominent Trump supporter in recent years. Zeldin voted against the Jan. 6 presidential election certification and was one the most vocal defenders of Trump's former president during the first impeachment.Trump will host an Aug. 5 fundraiser for New York Republicans. Trump has not publicly indicated whether or not he will endorse the race for governor.Giuliani doesn't expect to be endorsed until spring next year, if ever.I think he just sits it out. Giuliani stated that while I wouldn't turn down an endorsement by President Trump, but I also know his mind and how his political team works. If you have friends in a race you can just sort of wait and see what happens. My guess is that he waits until it becomes clear who he will be supporting.Even if Giuliani wins the primary, he will be an underdog in the general election. Since 2002, no Republican has won a statewide election here. The results have been very close in the past. Cuomos 2018 campaign messaging was successful because it pointed out that Trump's opponent was also registered in the same party. It might be difficult to imagine that a White House alum would break that streak.Giuliani believes there is a way, and it may be similar to that of his father who was elected mayor in New York City in 1993. He points out that crime was a major issue for Democratic voters in June's mayoral primaries, which were won by Eric Adams (an ex-NYPD captain who promoted a law-and order message).If that is the top issue for Democrats, then you will see that Democrats will vote for Republicans, or not vote at all. Giuliani stated that this gives me great hope that we would get the crossover vote that we need.Cuomo is also as vulnerable as ever. Cuomo is currently facing multiple investigations. These include an impeachment inquiry into allegations of sexual misconduct, the nursing home deaths scandal and claims that he improperly used state funds to help him write a novel. If he pursues his fourth term plans, he will likely face a primary with bruising.To have a chance of pulling off a seismic defeat against Cuomo, or any other Democrat Giuliani, you will need to first pull off a primary upset in order to win over voters from Republican strongholds such as Lewis County.Trump won 70% of the vote in the county. It might not be populated much, but it is the kind of place where a Republican who wants to run against the establishment can find success. The flag that was seen crossing the county line from south had a design similar to the MAGA banner but contained a nine-letter message. C-U-O–M-O was the last five.Giuliani stated that he feels like if he can make contact with these voters, he will be able to win the most votes.He stated that he would rather appeal to party leaders than the few who control them.