Post from Truth Social

A late-night thank-you note written in daytime prose

The post went up at 03:04 UTC on October 6, which is 11:04 p.m. Eastern on Monday, October 5. No travel is recorded for that evening, and the Ohio rally was two days earlier, so he was most likely at the White House. The hour points to Trump. The text does not. It runs as a sequence of complete, grammatical sentences with no drift and no self-interruption. The capitalization is regular and decorative ("Healthcare Innovation," "Technology Companies") rather than the erratic all-caps of his reactive posts. The middle sentence is a policy list: "drive Healthcare Innovation, LOWER COSTS, harness new technologies, bring together the best Doctors, Researchers, Healthcare Providers, and Technology Companies." That is the same structure as the Chuck Gray and Johnny Garrett endorsements posted the same day, which read "will fight tirelessly to Grow the Economy, Cut Taxes and Regulations…" This looks like a drafted template, posted or approved late at night. Trump's own voice shows in the framing devices he habitually adds or keeps: "my friend," "Our GREAT SENIORS!", "KEEP UP THE GREAT WORK!" and the signature block. The best reading is an aide draft with light personal tagging. Confidence is medium.

Who Howard Kessler is, and what the post leaves out

Kessler is a Boston and Palm Beach entrepreneur who founded Kessler Financial Services. He also funds the Commonwealth Project, which runs paid advocacy for medical cannabis and CBD access for seniors, including sponsored content arguing that Medicare could save money that way. The post describes his work only in generic terms ("Healthcare Innovation," "harness new technologies") and never mentions cannabis or CBD, his signature cause. That omission is the most informative thing about the text. It recasts a donor-advocate's specific agenda as broad senior-care modernization, which is easier to sell three weeks before the midterms. I found no public source for the title "Advisor on Aging Healthcare." The post may be the first public use of the title, or it may be an informal honorific.

Personality and motive

The post is warm and outward-facing, with a public transfer of status. Most of the trait signal is extraversion and positive affect ("incredible work," "tremendously successful"). Agreeableness shows here only in the conditional form typical of his praise posts: Kessler is a "friend" whose value is measured by success ("helped transform the financial services industry"). The communion content is real but goes through the speaker. Kessler is "working with my Administration," and the benefits come from "we." The agency motive is the credit-claiming that runs under the gratitude: the administration is "going to make sure they get it."

On the narrative level, Trump casts himself as the patron who gathers talent and hands out recognition, a King figure in its benevolent form. Seniors are the in-group who are owed something ("Our Seniors built this Country. They deserve the BEST Healthcare in the World"). That is a reciprocity frame aimed at a high-turnout voting bloc. It follows directly from the October 5 promise of "$5,000" to "all Adult Citizens" if Republicans keep Congress, and from a weak September jobs report. The post has no contrasting other. No enemy is named, so the splitting and devaluation that run through the same day's New York Times post ("STONE COLD LOSERS… going TO HELL") do not appear.

Clinical and defensive features

Narcissistic markers are muted. Idealization of Kessler is the only defense clearly at work ("tremendously successful entrepreneur and innovator," "incredible work"), and it is the reflected kind: praising an associate raises the standing of the administration that recruited him. This is maintenance-mode output, with no sign of injury or rage. It lands in the same news cycle as the Doral/New York Times grievance post, a few posts apart, and that juxtaposition is typical of the feed. Grandiose hostility and benevolent patronage alternate within hours, with no visible carryover of affect from one to the other.

Rhetoric

The devices are superlative ("BEST Healthcare in the World"), a nostalgic debt appeal ("built this Country"), glittering generalities ("vision, energy, and experience"), and emphasis through capitals on the two items that carry the campaign message ("LOWER COSTS," "GREAT CARE"). Nothing in the text identifies a target, dehumanizes anyone, or implies action against anyone. The polished syntax gives no evidence about cognitive status in either direction.

Sources: Washington Post Creative Group – The Commonwealth Project

Fact Verification

No formal appointment exists on the public record. I found no White House, HHS or CMS announcement creating an "Advisor on Aging Healthcare" post, and no reporting that Kessler was named a special government employee. Searching the raw source of Wikipedia's list of second-administration Executive Office appointments returned no hit for "Kessler" or "aging." Kessler's own materials don't claim a government title either. The Commonwealth Project's about page calls him "an entrepreneur and philanthropist" who leads the Kessler Initiatives. His April 1, 2026 paid press release, issued when the Medicare CBD pilot launched, signs him only as "Founder of The Commonwealth Project" and credits the administration for making real "the vision we helped champion."

He does, though, demonstrably advise Trump and senior health officials on seniors' health, informally. CNBC's December 2025 investigation (syndicated on Yahoo Finance) names him one of three architects of the cannabis rescheduling order and the Medicare CBD pilot. It says he "pushed and prodded Trump to sign." Bloomberg and Sechat report that he met HHS Secretary Kennedy and other HHS officials about a month before CMS moved to allow CBD reimbursement. At the Dec 18, 2025 Oval Office signing, Trump introduced "my friend Howard Kessler" and told him "I'm proud of you," and an official joked: "Howard Kessler, God bless you for being a pain in our sides... he's promised to stop calling you." Forbes (April 2026) credits the Medicare CBD reimbursement program "in large part" to his push. Trump also shared a Commonwealth Project video on Truth Social in September 2025.

So the substance holds: Kessler is a long-time friend whose advice on senior health Trump and his health officials have acted on. The capitalized, official-sounding title is the shaky part. It appears to be an informal label Trump gave him in this post, not a defined position. That gap is why this rates mostly true rather than true. | | "Kessler is a 'tremendously successful entrepreneur' who 'helped transform the financial services industry'" | Mostly True | Kessler founded Kessler Financial Services, known for co-branded and affinity credit card programs, and is a wealthy Boston and Palm Beach philanthropist. 'Transform the industry' is promotional framing, but it rests on a real business record. | | "Kessler is working with the Administration to lower healthcare costs and bring together doctors, researchers and technology companies for seniors" | Half True | The part that holds up is that Kessler works with the administration on senior health. He met HHS Secretary Kennedy and other HHS officials about Medicare coverage of CBD (Sechat, Bloomberg abstract). At the Dec 18, 2025 signing, Trump and his officials credited him by name for the executive order. That order rescheduled marijuana and directed a Medicare pilot for cannabinoid products. CMS launched the pilot on April 1, 2026, and Kessler's statement that day thanked "President Trump, Secretary Kennedy, Dr. Oz and the administration." Forbes credits the program largely to his push.

The post doesn't say what that work actually is. Every documented piece of it concerns hemp-derived CBD and medical cannabis for people 65 and older, and the post never mentions cannabis. The broader picture it paints is mostly unsupported:

• Lowering costs. The only cost figure I found is the Commonwealth Project's own unsourced claim of "approximately $60 billion in annual savings for CMS." Under the pilot as built, CMS pays nothing toward the products: participating providers absorb up to $500 per beneficiary per year (JMCO, Axios). I found no independent evidence that his work has lowered costs.
• Doctors and researchers. His group says its Healthcare Discovery Engine will "unite providers, payers, and researchers," and it cites Johns Hopkins research and Realm of Caring, a CBD nonprofit that joined its CMS initiative. That loosely matches the post, but it is the group's own CBD research program, not an administration effort.
• Technology companies. The group's homepage mentions using "real world data, AI, and strategic partnerships," but names no technology companies. I found no reporting of Kessler convening tech firms with the administration.

By contrast, every independent outlet I checked (CNBC, Forbes, Axios, Marijuana Moment, IVN) describes his involvement as cannabis and CBD advocacy, not a general healthcare innovation or cost program. The claim that he works with the administration for seniors is true. Its description of that work is a broad gloss on a narrow CBD and cannabis agenda, and the cost and technology parts are unsupported. |

Overall Veracity: 70%