A Journey Through Donald Trump’s Small-Dollar Fundraising Drive, In Ten Easy Steps

MONTOURSVILLE, PA - MAY 20: U.S. President Donald Trump tosses a hat into the crowd as he arrives for a 'Make America Great Again' campaign rally at Williamsport Regional Airport, May 20, 2019 in Montoursville, Penns... MONTOURSVILLE, PA - MAY 20: U.S. President Donald Trump tosses a hat into the crowd as he arrives for a 'Make America Great Again' campaign rally at Williamsport Regional Airport, May 20, 2019 in Montoursville, Pennsylvania. Trump is making a trip to the swing state to drum up Republican support on the eve of a special election in Pennsylvania's 12th congressional district, with Republican Fred Keller facing off against Democrat Marc Friedenberg. (Photo by Drew Angerer/Getty Images) MORE LESS
August 18, 2020 3:15 p.m.

This article is part of TPM Cafe, TPM’s home for opinion and news analysis. 

For a supposed billionaire, Donald Trump sure spends a lot of time asking me for money.

For the past three-plus years, his re-election campaign has touched my life as no president ever before, trawling for cash by email at least four and as many as eight times a day, six or seven days a week (doubled, in my case, since the emails come to two different addresses). And they’re not just asking for cash, they’re demanding it, in the most Trump-like ways. It is my burden, but I insist on sharing it with you now.

Trump campaign fundraising email.

Politicians and elected officials of all stripes often have no choice but to go shopping for dollars on line and, regardless of party, they do it with alarming, truth-deficient gusto. But the Trump campaign has set a new standard for presidential hucksterism. These emails contain an entire worldview: the distilled essence of the Trump fake-news narrative, as John Barron himself might tell it, laid out with painful clarity and mind-numbing constancy.

Frankly, I can’t see the sense in putting the touch on me 50 times a week. I’m a lifelong registered Democrat, for one thing. And — you could ask anyone — not a Trump fan. It’s possible the campaign’s punking me, I suppose, but, more likely, it’s my own damned fault.

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You see, back in 2017, I deigned to answer a survey from the campaign, which asked, more or less, “How’m I doing?”

The choices were “Great,” “Very Good,” “Good” or “Other.” Selecting “Other,” I explained in the provided text box that the President’s performance had been “Not So Good.” So much so, I opined, that he stood an excellent chance of going down in history as the worst American president ever.

That ought to throw them off the scent, I chuckled to myself. But I was wrong. The barrage — emails and the occasional robocall — never ended.

After a while, I began reading more closely. The campaign’s relentless literary assault, it emerged, is at once scary and amusing. Filled with self-celebratory paeans to Himself, typically at serious odds with reality, they are at the same time unmistakably mean-spirited and brimming with provocative falsehood tailored to generate outrage among the low-dollar donors who Trump emails call Patriots with a capital “P.” While wealthy donors are invited to fancy $580,600 a plate dinners in mansions, we hoi-polloi are treated to a written rendering of a late night televangelist’s infomercial, with none of the sincerity plus additional paranoia and vituperative bile thrown in as a bonus. Can a President even talk like that? I find myself wondering. Yes, apparently, he can. Over and over and over again.

With time, I’ve noticed recurring patterns in the Trump pitches. Not because I’m so clever, but more because they are often word-for-word identical to ones received earlier in the re-election drive.

These include:

1. They’re Out To Get You

On June 17, this news-distorting missive regarding the President’s scheduled Tulsa rally arrived in my inbox:

“First, they support tens of thousands of ANTIFA THUGS DESTROYING our communities.

And now, they try to COVID-SHAME us for holding rallies at only a fraction of the people?


From there, the pitch swiftly segues to engage one of the most crucial elements of Trump’s psychological appeal to his base, their own insecurities and sense of aggrieved victimhood, which they share with him:

The Liberals have ALWAYS been trying to take me down, and more importantly, they’ve been trying to take YOU down, Jamie.

They hate me. They hate you. They hate rallies and it’s all because they hate the idea of MAKING AMERICA GREAT AGAIN!

And then on to the pitch, with de rigeur arbitrary deadline:

We are halfway through the month and now the Left has tried to SILENCE US, I want to make a statement SO LOUD that even the Fake News media won’t be able to ignore us.

How will he do that? By raising more money by an FEC reporting deadline than the libs expect, blowing their minds, and further enabled by the crafty invocation of Trump’s signature move, the Dubious Grand Flourish, in this case promising mysterious matching funds somehow available to him to multiply citizen donations. Which is where my credit card was supposed to come in. But didn’t.

2. You’ve Been Chosen

Many a solicitation from the campaign kicks off with an attestation of the rigorous research that’s identified me as the highly qualified, lucky someone to receive this incredible offer.

For just about every one of the last 1,305 days, I’ve been invited on the amusing basis of my allegedly impeccable Trump-supporting bona fides to hurry up and donate. The long list of invitations I’ve received (many of which are repeated 3 or 4 times in a cycle only to return later for additional repetition) include not just the opportunity to become an official Trump Executive Member, but also to earn my spot as an Official 2020 Trump Presidential Founder, a charter member of the 2020 Presidential Task Force, the 2020 Trump Presidential Advisors and ascension to Trump Life Member status. I’ve been offered a chance to support the Trump Rally Defense Fund — “they don’t want me to have my rally” (and for good reason) — and to secure my place on the Trump Official Donor List.

I’ve also been asked to join the Trump 100 Club (the most exclusive 100 donors, you see, with only nine spots left), to sign the Stand With Trump Initiative, to fund the Trump Ad Blitz fund, and place my name on the Trump Donor Wall.

Then there are the surveys I’m always being implored to answer: The Official Mainstream Media Accountability Survey, Official 2020 Campaign Strategy Survey, Official Trump vs. Democrats Survey, Official 2020 Census Survey, Official Unlawful Spying Survey, and so on and so forth (there are dozens). Aside from trousering my cash, a secondary purpose behind such invites seems to be to firm and codify the upside-down recitation of the real world with Facts a la Trump.

In each case, I am advised, the President is waiting on tenterhooks for my response. But if I don’t send cash, my prospects vaporize. Until next time.

On the bright side, responding to the surveys is never laborious. The giddy MAGA Rally Prep Survey I got last week put but one question in to me in its main body: “Do You Believe President Trump is prepared to lead the greatest comeback in American history?” Answers: Yes or No.

“No,” I answered, and was promptly thanked and offered a chance to donate money to the campaign.

3. We’re Watching You, You Better Not Let Us Down

As Donald Trump, Jr., warned on behalf of the campaign in his best junior gangster style the other morning while soliciting a handout under the doleful heading, “My Father Needs You,” “You’ve been such a key part of our success over the last few years, and I’d hate to see your fantastic support go unrecognized.”

That would be a shame, for sure. Meanwhile, the sad truth of it is, letters from Trump family members — Donald, Jr. and Eric, Eric’s wife Lara, very occasionally Melania, but never Ivanka or Tiffany — appear in my inbox far more frequently than those from my own family. The fundraising themes, though not entirely dissimilar from those of my kin, are even more consternated and urgent. Occasionally Mike Pence and Mother chime in. Newt Gingrich has been known to turn up as well. Liberated by the free style ethos and next-level reality distortion of the Trump brand, Gingrich, the veteran confabulator, really gets to push the outside edge of the well-worn envelope of his own absurdity.

4. You Could Win

There may have been no quid pro quo sought from the Ukrainian president, but when you are asked to give something to Trump, his campaign expects that you want them to offer you something in return. Yet, it turns out, something is not really something, but rather a chance to win something. And, if we are to be honest, the odds are miserable.

Ofttimes, they invite me to enter a contest to go somewhere to hang with the President, which alas can only be achieved by donating some money for a chance. On June 15, I got from the President himself:

I have a HUGE announcement that I’m only sharing with my TOP supporters.

We will be celebrating the 2020 Republican National Convention in the great State of Florida and I’ve requested that YOU be there with me as my special VIP guest.…

Please contribute ANY AMOUNT TODAY to win this once-in-a-lifetime opportunity to come celebrate the 2020 Republican National Convention as my VIP Guest. >>

The chance to meet the great man is sometimes predicated on installing the Trump App, and (as always) my entry requires that I donate for a chance to make this dream come true. Even though the tickler I received said I’d have to use the Trump App to earn points to compete, this request and another two weeks later upped the stakes to a “guaranteed” opportunity to meet him if I downloaded it, though if we are to be legalistic, a guaranteed opportunity to meet is not the same as a guaranteed meeting.

Two weeks later, I’ve still failed to download the app, but a new, superheated entreaty ups the stakes.

This is a GUARANTEED opportunity to meet your favorite President and all you have to do is download and use the Official Trump 2020 App. When you meet President Trump, you’ll even get to take a picture together so that you can cherish the moment forever.

We’re sending the President a list of everyone who downloads the app today. If you act within the NEXT HOUR, we’ll make sure your name is at the TOP of the list he sees.

Since no money was involved, I downloaded the Trump App in the spirit of scientific inquiry and a screen popped up that said:


Since you’ve proven your [sic] a loyal supporter and signed up to download the Official Trump 2020 App, President Trump has authorized a TRIPLE-MATCH on your next contribution.

This offer is only available for the NEXT HOUR, so you need to act fast.

Please contribute ANY AMOUNT in the NEXT HOUR and your gift will be TRIPLE-MATCHED!

But it turned out I couldn’t really use the app, without coughing up some dough. Venturing deeper in, a bevy of fine print explained that by using the app (following my donation) I was entering into a legally binding agreement with Trump, his campaign and the RNC, and that I waived my right to a jury trial, participate in class actions and that the program will terminate on October 30, before the election, with no value awarded to the points I’d collect, which are non-transferable. The campaign also reserves the right to “amend, modify, supplement or cancel the program” and its terms at its sole discretion. Score! Wait. No class actions or jury trials? What do they know about their fund raising that we don’t know?

Meanwhile, now that the Florida convention has been cancelled, what are the chances that those who donated will get to meet the President? Will they be entered into the next contest, gratis? My first guess would be no. Come to think of it, so would my second.

5. No Quid Pro Quo, You Quid Pro Quo

Everything at TrumpVictory.com is a contest. And unsurprisingly, gold is a major theme of all Trump correspondence. Hence, the first offer to vote to help select the design for the already-mentioned official Trump Gold Card, which came in on March 6. Its exact worth was hard to quantify, however, as it claimed to offer holders unspecified privileges that come from being “the most important group of donors in re-electing President Trump.” So why a contest?

Originally we were planning on releasing just one design, but when President Trump saw the cards on his desk, he said, ‘Why would you ask me? Let the American People decide – they ALWAYS know best!’

Fortunately, by March 7, they had winnowed the original five choices down to three without my help. They then asked me to chime in again.

President Trump really values your input and has made it clear that he wants YOU to play an important role in our campaign as we head into November.

Americans from all across the Nation will proudly carry these membership cards as a sign of their unwavering support for OUR President, and President Trump is trusting YOU to select the best one.”

So now it’s up to you, Jamie. What do you think? We’re only counting responses until 11:59 PM TONIGHT.

We’re sending the President the results first thing TOMORROW morning, and we know he’s going to ask which one you voted for. Don’t let him down.

On March 8, I still hadn’t cast my vote but the campaign had narrowed it down to two choices.

President Trump asked us to reach out to a few of his TOP supporters, like Jamie from New York, to vote on which of the Membership Card designs you like the best.

A vote from me was again not forthcoming (the cards seemed to me to be steeped in Nazi iconography) but on March 11, Mr. Trump himself wrote in a state of high jubilation to announce the final results:


You voted and my team listened.

I told my team to let everyday American Patriots, like YOU, pick the design of our BRAND NEW Gold Card, and I couldn’t be happier with the result. In fact, you picked the exact same card I did – I knew you wouldn’t let me down.

After receiving over 500,000 votes, I am proud to present you with the beautiful Gold Card that was voted the WINNER by YOU:

Official 2020 Trump Gold Card Members from all around the Nation will be THE MOST important group of supporters when it comes to our re-election efforts, and I really want YOU to be a part of it.

To join, all you have to do is contribute $35 and you’ll automatically become an Official 2020 TrumpGold Card Member and receive your PERSONALIZED Gold Card.

Please contribute $35 or more by 11:59 PM TONIGHT to activate your membership and we’ll send you your PERSONALIZED Gold Card. >>

Actually, I hadn’t voted. And as I wrote this piece, offers started streaming in for the Trump Platinum Card, beginning with the same contest to pick a card design. Once again, I was credited for choosing the winner, even though I didn’t vote.

Trump campaign fundraising email

6. I Want To Meet You

On June 7, President Trump wrote “I Want to Meet You,” inviting me to pay to enter a contest for me and a guest to meet him at an upcoming, still-to-be-announced rally, with flight, meals and “a very nice place to stay” included.

This is but one of dozens of different offers I’ve received from the President asking me to fork over for a chance to win dinner and have my picture taken with our Commander in Chief. Not only couldn’t I win, (I didn’t give him money, duh,) but seems possible that nobody did. Writing about these phantom dinners with the President, in Popular Information last November, Judd Legum observed that the Trump campaign has never once named or posted a picture of a winner in what had already been fifteen competitions to win a presidential dinner.

Which put Trump’s remarks of June 10 — “This is the greatest part about being your President. I love getting to meet the people who truly are the heart and soul of our beautiful Nation. You are my motivation to keep fighting for four more years!” — into a potentially disturbing perspective. Could my “favorite president” be less than forthright?

7. Don’t Hurt His Feelings

Based on the campaign’s correspondence with me, the President is a delicate flower, easily hurt and in need of constant reassurance, which largely comports with what we know about the offline personality of a man who, in addition to all his other sterling qualities, also turns out to be omniscient and impossibly detail oriented.

So concerned are close family members and associates about keeping the president’s mood up, they often write on his behalf.

Donald Trump, Jr., for example:

My father asked me to reach out because he noticed that your name was MISSING from the list of supporters whose names will be broadcast LIVE during tonight’s State of the Union Address.

Do you not stand with my father?

Trump himself is not above getting in my grille for not helping cheer him up with a cash donation, writing four times — May 23, 24, 26, and June 1, with essentially the identical message. His May 23 epistle is headlined, “I’m Offended”:

Why haven’t you accepted your invitation to become an Official 2020 Trump Life Member?

Trump Life Members are going to be the lifeblood of my 2020 campaign, and I am going to be leaning on this group to play a crucial role over the next few months.

Another way to make President Trump feel better is to sign his birthday card. Birthdays are talismanic in a Rosebud sort of way for Trump and his family insists I need to know this and do something about it, pronto.

June 13, Lara Trump writes, echoing earlier cards from her husband, Eric Trump, Donald Trump., Jr.:


President Trump’s birthday is tomorrow.

We always give him a birthday card filled with messages from Patriots around the Country, but this year we want to go even bigger. We want to surprise him with 2 MILLION signatures and make it our biggest card yet.

Hearing from Patriotic Americans like you is President Trump’s FAVORITE part of his job, and I don’t want him to be disappointed. It would mean a lot to him if you could take 30 seconds to add your name to his ONLY Official Birthday Card.

Please add your name NOW to the President’s ONLY Official Birthday Card and leave a special note for him. >>

President Trump will be disappointed if he doesn’t see YOUR name on the list of Patriots who signed his ONLY Official Birthday Card, and I know you don’t want to let him down.

The following day, June 14, 2020, at 10:08 a.m., the campaign itself checks in with news of “The President’s Birthday.” Don’t tell him we’re cooking up a card:



Today is President Trump’s birthday and, with your help, we want to surprise him by having our BIGGEST fundraising day EVER!

We need to raise $10 MILLION in ONE DAY to set a new daily record.

You’ve always been such a loyal supporter of the President’s, which is why we’ve decided to EXTEND your TRIPLE-MATCH offer until 11:59 PM TONIGHT to help us CRUSH our goal.

President Trump has no idea that we’re planning this surprise for him, so please, DO NOT forward this email to anyone.

Please contribute ANY AMOUNT by 11:59 PM TONIGHT to help us CRUSH our $10,000,000 goal and your gift will automatically be TRIPLE-MATCHED. >>

At 3:18 p.m., a Trump birthday alert arrives, suggesting they’re not done yet:


TODAY is President Trump’s Birthday and we noticed that you STILL haven’t signed his OFFICIAL Birthday Card.

Remember, this is the President’s ONLY Official Birthday Card, and when you sign your name you can even leave him a personal note to read.

This is your LAST CHANCE, Jamie.

We’re giving the card to President Trump TONIGHT, so don’t miss your chance to PERSONALLY wish him ‘Happy Birthday’ before it’s too late.

Please sign the President’s ONLY Official Birthday Card by 9:00 PM TONIGHT to make sure he sees YOUR NAME. >>

But it’s not my last chance, after all. June 14, 2020, 5:41 p.m.: Lara Trump writes again with the same message.

I don’t sign the card. There follows the inevitable scolding:

Trump campaign fundraising email

But not all is lost.

8 . Ye Olde Gift Shoppe

June 15, 11:54 a.m.: TrumpStoreAmerica checks in with the exciting news that yesterday was “a great coincidence,” being both Flag Day and President Trump’s birthday and, silly me, I forgot to wish him a happy birthday! Now’s my chance to repent and place an order from the Trump Store. I’ll have to pay for those Trump lawn signs to plunk down in front of my house but because of the celebration of this once-in-a-lifetime coinkydink they’re on sale.

Personally, I’m thinking I’d prefer the offer that came in five days earlier. “President Trump really appreciates your unwavering support, so he’s asked us to give you PRIORITY ACCESS to get your Trump MAGA Dad Whiskey Glasses before anyone else.”

Trump campaign fundraising email

What with Trump being an avowed teetotaler, his brother having died from illness related to alcoholism, MAGA Dad whiskey glasses seemed an odd choice for Trump branding, but there’s surely been weirder ones, a buck is a buck and at $30 for two cheap glasses, someone’s making one. Then again, I could use a drink. Possibly even more than I can use a personalized Trump-Pence Welcome Mat, mine free at just $75.

Trump campaign fundraising email

A later offer for patriotic face masks was discordant, given the President’s refusal to wear them.

9 . The 200-, 300-, 400-, 500-, 600 and 700-Percent Match

As we’ve seen, the best way to cheer President Trump up is to send him money. But in case you’re still feeling reticent, the President frequently draws upon a magical power to multiply donations at will. When Trump was riding higher in the polls, he would roll out the 200% match, with 3x and 4x matches more sparing, invoked for special occasions only. But lately it’s been 500% matches pretty much all the time. Last month a 600% match broke cover and just the other day there was a temporary 700% match. Meaning, there’s never been a better time not to give, ever!

I’m putting all my trust in you, Jamie.

Our End-of-Month Deadline is TOMORROW, and I set a MASSIVE goal of raising another $25 million. This is our biggest goal yet, so why haven’t you stepped up?

Not crushing our goal is NOT an option. I really need you to contribute, which is why I’m going to do something I’ve never done before in the hope that you’ll join me in making history.

For the NEXT HOUR, all contributions made to our critical $25,000,000 End-of-Month Goal be not 500, not 600, but 700%-MATCHED!

I need to know that I can count on you right now, Jamie.

The Trump Finance Team is sending me a list of EVERY Patriot who contributes in the NEXT HOUR. Make sure I see your name.

Please contribute ANY AMOUNT RIGHT NOW for a 700%-MATCH and to get on the list I see next.

Thank you,

Donald J. Trump

President of the United States

Strangely, somehow the 700% match offers haven’t stopped coming, along with the 300, 400 and 500 and 600% ones. This morning at 12.35 am, The Donald said it was my last chance to contribute with a 600% matching donation. But by 9.50 am, he was inviting me to donate to enter a new contest to meet him in the Hamptons for dinner, with a 600% match to accompany my tithe. Clearly, when you’re a MAGA fan, short-, medium- and long-term memory loss is a big plus.

Not that it likely matters. As the non-partisan Center for Responsive Politics, which studied the matching phenomena — employed regularly by fund raising campaigns — has observed, “Limited-time matching gives ideological supporters extra incentive to donate to a campaign they care about. But legal experts say it is hard to see how donation matching could happen given campaign contribution limits. And there are no accountability mechanisms to determine whether campaigns actually follow through with their promises.”

Given Trump’s extensive track record of not following through on promises to give and the near complete abdication by the FEC of its oversight responsibilities, there is no reason to be suspicious, is there? Same with double entries to contests he promises but only if you enter now? Since no one ever seems to win, they’re just twice as many chances not to win.

10 . Memorialize Yourself

In honor of supporting his vaunted wall to keep out Mexicans, faithful Trump backers were asked to commemorate their support with a donation to help build a wall honoring donors like themselves who supported the president and his wall.

Sept 16, 2019

America is GREAT again. Now it’s up to YOU to Keep America Great!

Since you’ve been such a great supporter, I want to offer you something very exclusive. (Don’t share this offer!)

I am dedicating a wall for a select group of donors who choose to step up at this critical time. Space is limited on the Official 2019 Trump Donor Wall, so be sure to act fast!

This is the best time for you to make your VERY FIRST contribution to my campaign, and cement your name in political history.

Please make your best contribution before 11:59 PM TONIGHT to be one of the FIRST donors to have their name permanently engraved on the Official 2019 Trump Donor Wall.

It was an appealing pitch, so I wrote with some not unreasonable enquiries about the Donor Wall. When and where would it be erected?? Out of what material might it be constructed? Could I be there at the unveiling and would I be permitted continue visit for the rest of my life? And, most importantly, I wondered, how large were the letters in my name going to be and in what font? I’m still waiting for answers, yet they keep asking.

In Closing

It’s the rare commander in chief who asks the public to make him feel better by giving him money, but that’s Donald Trump for you. When it comes to hoovering up your money, he won’t take no for an answer. And with his 2020 fund-raising underscores more than ever why we need publicly funded elections. Begging is distasteful, begging by purported billionaires whose fundraising pitches are fraudulent in almost every detail — except for the fact that you are indeed giving money to him — even more so.

All of us are needier, greedier, and more thin-skinned than we’d care to admit. But there’s a reason we don’t admit it — it’s gross. Trump, in permanent campaign mode, has no such compunction. All the desperation, hurt and self-pity that is central to his curious persona and appeal, plus generous lashings of his trademark narcissism and boasting, are on display here. Please make it stop.


Jamie Lincoln Kitman is a lawyer, writer and band manager.

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