Donald Trump was “not happy” with Kimberly Guilfoyle. So she resigned from “the honor of a lifetime” as ambassador to Greece.

Guilfoyle surely thinks she deserves better. She’d prostrated herself for the Trumps, literally and figuratively, and became the brunt of ridicule at the 2020 GOP convention when she maniacally screamed from the dais that “the best is yet to come.”  

Maybe, but not for her.

The Wall Street Journal reported that Guilfoyle, a former prosecutor, left an incriminating paper trail, including asking a Trump donor to pay off her $100k AmEx bill in exchange for giving him access to the White House. The State Department inspector general is said to be investigating.

The former Fox News personality came about her diplomatic appointment as a golden parachute, a “win-win” after Don Jr. dumped her in 2024 with merely an engagement ring. Daddy Trump dispatched his never-to-be daughter-in-law across the ocean to the Cradle of Democracy, out of his sight, and apparently out of her mind.

In May of this year, DJT Jr. poured salt water onto Guilfoyle’s searing humiliation by marrying Bettina Anderson on a private Bahamian island (you know, with a Russian oligarch footing the tab).

Guilfoyle must have wondered, don’t I get a sugar daddy too?

Little doubt, she’s signed away with NDAs her right to tell-all. But no matter, with the IG looking at her grift, she’ll be prostrate again, begging for a presidential pardon.

Indeed, Guilfoyle is on script: “While my time as Ambassador may be coming to an end, my commitment to President Trump, the America First movement, and the country I love will never end.”

But dang, Kristi Noem got to be the Special Envoy for the Shield of the Americas, whatever that is, after she rained down bad press on Trump as Homeland Security secretary. Kimberly Guilfoyle has earned at least a comparable sinecure.

It’s all pretty normal, right? Rent out a private Bahamian island for your wedding celebration. And a Russian oligarch foots the bill.

Meet Umar Kremlev, who generously gifted this fantasy fête to Donald Trump, Jr. and bride Bettina Anderson in May. What a guy.

Umar’s given surname is Lutfulloyev. He changed it to Kremlev, meaning “of the Kremlin.” Perhaps if you were looking to curry favor in Moscow but were born in Tajikistan, had a biker gang history and a criminal record of battery and extortion, you’d change your name too.

It worked. In 2021, Vladimir Putin appointed Kremlev's company, TsUPIS, the sole operator of all bookmaker betting in Russia and, conveniently, Kremlev also controlled the Unified Gambling Regulator, overseeing TsUPIS’s betting activities. Gee, hard to see how Umar got filthy rich.

With Putin’s blessing, Umar was elected president of the International Boxing Association in 2020 and proceeded to name Gazprom, Russia’s state-owned energy company, IBA’s sole sponsor. Then he suspended Ukraine from the IBA.

Not surprisingly, the fuddy-duddies found something smelly about Umar’s largesse toward DJT Jr. Jordan Libowitz of CREW, Citizens for Responsibility and Ethics in Washington, snickered that "People don't just give hundreds of thousands of dollars to a random acquaintance without wanting something." Even GOP Senator John Curtis is flummoxed: “A toaster is a wedding gift. A private-island party paid for a Putin-connected oligarch is something else.”

Curtis wants Judiciary Committee chair Chuck Grassley to subpoena Donnie to a hearing to learn more.

Nothing is yet scheduled.

Sgt. Gannon Ken Van Dyke made a highly educated wager and won around $375k on the prediction market Polymarket, betting that the US military would remove and capture Nicolás Maduro. Of course, it didn’t hurt that Van Dyke possessed classified information about the plan to abduct Venezuela’s head of state.

While Van Dyke is facing federal wire fraud charges, his case illustrates how prediction markets, in which you can wager on pretty much anything, incentivize insider trading, bribery, cheating, and corruption. After all, Van Dyke is far from alone: There have also been suspiciously timed bets and big payouts following the ouster of Ayatollah Ali Khamenei and military actions against Iran.

Prediction markets are exploding: The Wall Street Journal reported that total trading volume on Polymarket and Kalshi soared to $24.2 billion in April 2026, compared to $1.8 billion just a year before. Wow!

Donald Trump used to disapprove of prediction markets. But that was then. He recently posted on Truth Social that state lawmakers seeking to regulate these markets are “SCUM.” Perhaps his change of heart has to do with Don Jr.’s investment firm raising $300 million for Polymarket and Junior being a highly paid advisor to both Polymarket and Kalshi. Not that he would ever leverage his family ties to enrich himself!

Or maybe it’s that DJT’s Truth Social is now openly marketing access to administration insider information—to its $100k per month subscribers—info a canny subscriber can cash in on bigly on prediction markets.

Trump now insists that only the federal Commodities Futures Trading Commission may regulate prediction markets. And Trump’s CFTC is way more about promoting than regulating these online casinos.

Public Citizen, Americans for Financial Reform, Citizens for Responsibility and Ethics in Washington, the Project On Government Oversight, and Democracy Defenders Action are all backing the STOP Corrupt Bets Act, proposed by Sen. Jeff Merkley and Rep. Jamie Raskin to ban prediction market betting on elections, government actions, sports and military actions. (You could still bet on sports through state-regulated platforms.)

Any wagers on the outcome?

Have a need to ditch a fiancée? Maybe, like Don Jr., your pops can appoint her ambassador to the “Cradle of Democracy.” 

Itchy to grift out? Maybe, like Don Jr., you could join investment firm 1789 Capital and secure government contracts, loans, and regulatory relief for clients like Polymarket which saw its value skyrocket from $300 million last year to $15 billion after a federal regulator lifted the ban on US wagers and granted it an operating license. Such good deeds for clients get richly rewarded: Over the first half of 2026, 1789’s profits have shot up 200%; its assets under management mushroomed ten-fold. 

Donnie must be very talented. Or something.

But Eric gets a piece of the action too. Together, the Trump bros have taken stakes in a dozen defense companies during daddy’s second term, tallying at least $3.2 billion in direct government business and $3.1 billion more in future options.

Which is only fair, given that bro-in-law Jared’s private equity firm Affinity Partners has raised $3 billion, $2 billion from the Saudi sovereign wealth fund, Qatar, and the UAE , while serving as DJT’s Special Envoy for Peace.