Good morning. Smart money, free money and taxed money — today's issue covers all three.

On The Money Today:

  • The Wall Street legend who called 1987 has a warning for your portfolio

  • A $1,000 yearly retirement match — and Trump wants more Americans to get it

  • What Jamie Ding's $880K "Jeopardy!" win actually pays out after taxes

Let's get into it.

Jones saw the 1987 crash coming before Wall Street knew what hit it — and walked away $100 million richer. Now he's sounding the alarm again. He says the S&P 500 is more dangerously overvalued than 1929 or the dot-com bubble, and that the index funds sitting in your retirement account today could be worth less in ten years than what you put in. What he's doing with his own money right now is worth paying attention to.

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The federal government will match your retirement contributions dollar-for-dollar — up to $1,000 deposited directly into your account every year. Until now, it's been limited to lower-income earners. Trump just signed an executive order to expand it to all working Americans — and if it passes, qualifying could be as simple as making a contribution. Here's who gets it today and whether you'd be next.

Jamie Ding just wrapped a 31-game winning streak and is heading home with $880,000. His plan — donate some, save the rest in a high-yield savings account — sounds solid. But before any of it lands, the IRS gets first dibs. Game show winnings are taxed as ordinary income, which means the bracket you land in could cost you more than you'd ever guess. What Ding's windfall reveals about handling a sudden financial windfall applies whether you win it, inherit it, or stumble into it.

MONEY IQ

What is the largest amount ever won on Jeopardy! in regular season play?

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ALSO MAKING THE ROUNDS TODAY

NEWS: If you own property or earn good money in New York, a major tax debate is heating up that could hit your wallet directly

RETIREMENT: If your home is worth millions but your savings aren't, retiring early may not work the way you think it will

INVESTING: Elon Musk gets a massive bonus if he puts a million people on Mars — here's what's in his SpaceX deal and why it matters to investors

MONEY IQ ANSWER

Answer: D — $2,520,700, won by Ken Jennings over 74 consecutive games in 2004. Jamie Ding's $880,000 run puts him 5th on that all-time list — and like Jennings, he'll be sharing a chunk of it with the IRS.

That's a wrap for today! Before you go, we'd love to know what you thought of today's newsletter. Hit REPLY if you have more to share — we read every one.

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See you soon with another quick roundup of the financial news that matters.

Today's newsletter was written by Shirley Sze and edited by Rudro Chakrabarti. Stories by Em Norton, Godwin Oluponmile, Joanna Sinclair, Amanda Smith, Becky Robertson, Monique Danao and Chris Morris.

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