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‘Winning Grandpop’ Strikes Again With Second Big Powerball Win In Maryland

A Baltimore County man who has been playing the Maryland Lottery since day one has proved that lightning really can strike twice—scoring his second major Powerball win in just two years.

The lucky Woodlawn resident, who fittingly goes by the nickname “Winning Grandpop,” claimed a $150,000 third-tier Powerball prize on Thursday, March 14, officials announced.

And this isn’t his first rodeo.

“Winning Grandpop” said he’s been "winning for years"—including a $50,000 Powerball payout in 2023.

“I’ve always said I would win again—and I’m back!” he declared after snagging his latest six-figure prize.

His ticket, purchased at Woodlawn Shell on Security Boulevard, was initially worth $50,000, but because he added the Power Play option, a 3X multiplier boosted his winnings to $150,000.

Google Maps street view

According to the Maryland Lottery, the longtime player was “floored” when he scanned his ticket and realized he hit it big again.

When asked about his plans for the prize money, he said he intends to help a few close family members and save the rest.

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