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New York is holding party primaries on June 28, 2022 for local and statewide offices. The showcase statewide primary is for Governor, with Democrats and Republicans heading to the polls to choose nominees for the general election in November. I will be voting in the Republican Primary on the 28th. In this article, I will detail the great and very expensive efforts that one of the four Republican candidates for Governor, Mr. Harry Wilson, has undertaken to win my vote.

Harry Wilson wants my vote more than I expected.

The Republican Primary Field In New York

I have noted in previous articles on New York City elections that I am registered to vote in New York as a Republican. Because this article is about the remarkable amount of mail that I have received from one of the four Republican candidates, Mr. Harry Wilson, I will only be covering the candidates running for the Republican nomination for Governor of New York.

I present the four Republican candidates for Governor in table form:

CandidateCurrent/Previous OfficeWebsite (Archievd)
Rob AstorinoFormer Westchester County ExecutiveLink
Andrew GiulianiFormer Special Assistant to President Donald TrumpLink
Harry WilsonBusinessmanLink
Lee ZeldinU.S. Congressman For NY-1Link

Mr. Zeldin, a United States Congressman, is the presumed front-runner in the race. He received the New York Republican Party’s endorsement at the GOP Convention last spring, raised the most money, and has led the small number of pre-election polls.

Mr. Astorino, the former Westchester County Executive who subsequently lost close races for New York State Senate and the U.S. House, has generally polled in third or fourth place, but finished second in one June poll. Mr. Giuliani, the son of former New York City Mayor Rudy Giuliani, has generally polled the second strongest behind Mr. Zeldon. Mr. Wilson, a businessman who lost a competitive race for New York Comptroller in 2010, is self-funding his campaign, putting him close to financial and resource parity with Mr. Zeldin.

Harry Wilson Wants My Vote

I seldom receive campaign literature for New York races. No Republican has won a statewide race in New York since 2002 (Mr. Wilson’s narrow loss for Comptroller in 2010 was the best effort). The Republicans have generally avoided primaries in statewide races in New York in recent elections – the last contested gubernatorial primary occurred in 2010 when Mr. Carl Paladino defeated Mr. Rick Lazio. Republicans have not been competitive in a New York City-wide election since 2005, the last election in which former Mayor Mike Bloomberg pretended to be a Republican, and the New York GOP has no presence at all in my area of Brooklyn in more local races.

Thus, I was surprised when on or about June 12 or 13, I received a two full color, expensive campaign mailings from Mr. Harry Wilson, asking for my vote for Governor. Note that I received both mailings in the same batch of mail – I check my mail on a daily basis unlike one-half of The New Leaf Journal’s comedic dialogue duo. What started as a novelty turned into an avalanche. By June 23, 2022, I had received a total of nine expensive campaign mailings from Mr. Wilson. See the collection below:

Nine campaign mailings from NY GOP Governor candidate Harry Wilson.

The mailings vary in tone. Two of them are purely positive advertisements touting Mr. Wilson’s plan to turn New York around.

Two positive campaign mailings from NY GOP Governor candidate Harry Wilson.

Two of the mailings purport to contrast Mr. Wilson’s experience and positions with Mr. Zeldin’s. In these mailings, it is immediately obvious that the sender is the Wilson campaign.

Two campaign mailings from NY GOP Governor candidate Harry Wilson contrasting him with Lee Zeldin.

However, five of the mailings are a bit darker. The negative mailings are straight-out attacks against Mr. Zeldin, most often insisting that he was a supporter of former New York Governor Andrew Cuomo (not the most popular figure in New York Republican circles) and would govern similarly. Lest one think that accusing a Republican running for Governor of New York of being Mr. Cuomo’s “wing-man” is the gravest attack that one could muster, another one of Mr. Wilson’s ads (disingenuously) accuses Mr. Zeldin of aligning with Congresswoman Alexandria Ocasio-Cortez against funding for the New York Police Department because they both opposed a large spending bill in Congress that happened to include a small amount of funding for the NYPD (under Mr. Wilson’s logic, many of the members of the House’s conservative Freedom Caucus are thus also secret acolytes of Ms. Ocasio-Cortez).

Five negative campaign mailings from NY GOP Governor candidate Harry Wilson attacking Lee Zeldin..

What is interesting about Mr. Wilson’s attack ads is that they are very circumspect about noting that the sender is the Wilson campaign. The back of the mailings note that the sender is “Taxpayers for Wilson” – but there is no reference to Mr. Wilson anywhere on the mailings other than the disclaimer about the sender.

Questions

While I am flattered by how much Mr. Wilson wants my vote and, any caveats about his platform aside, he does appear to have made a very successful career for myself in business, I have serious questions about his campaign strategy. Printing large, full-color campaign mailings is expensive. Mailing them is also expensive. To be sure, Mr. Wilson is not being stingy about self-funding his camapign. According to a NY1 report from June 7, Mr. Wilson had loaned his campaign $12 million, and had spent more that $7 million as of that date. However, for what he is spending, he is far from the spending levels of former Mr. Bloomberg, the former Mayor of New York City, who famously carpet-bombed the airwaves en route to securing three terms in office.

In light of the foregoing, I ask why Mr. Wilson is spending so much for the vote of one person. While New York is not a Republican stronghold on account of the fact that about 40% of the state’s population lives in the overwhelmingly Democratic New York City, New York is the fourth largest state in the United States. For that reason, and there are many Republicans in New York. Logic dictates that few of these Republicans are receiving the special attention from Mr. Wilson that I am.

What makes my vote so valuable? Only the people who Mr. Wilson is paying to send me too much mail know the answer.

Did Mr. Wilson’s Ad Blitz Work?

Mr. Wilson is the only New York gubernatorial candidate who has sent me mail. He has sent me a great deal of mail. Surely this great expense he has made from his personal funds will have won the vote of at least one Brooklyn voter.

Alas for Mr. Wilson, I had already narrowed the field for purposes of deciding who I will vote for to Mr. Astorino and Mr. Zeldin before I received a single campaign mailing. In fact, I already knew who all the candidates were and their major positions – including those of Mr. Wilson – and determined that I could not vote for Mr. Wilson in the GOP primary given the available alternatives. Worse yet for Mr. Wilson, barring a dramatic change in the next 48 hours, I intend to cast my vote for Mr. Lee Zeldin to be the Republican nominee for Governor of New York. (Things may have been different had Mr. Astorino not encouraged voters to follow him on TikTok in the first debate.)

While Mr. Wilson will not win my vote in the primary, all hope for him is not lost. I will vote for the nominee in November regardless of who the Republican voters of New York, in their collective wisdom, choose to represent the GOP in the general election. However, in the event that the voters choose Mr. Wilson, my general election vote for Mr. Wilson will have absolutely nothing to do with the exorbitant amount of money he spent packing my mailbox over the last two weeks.

Perhaps Mr. Wilson would have had a better chance of winning my vote in November had he spent more of his money in June on persuadable voters.