It’s not every day someone calls Dave Ramsey because their dad—who’s also a lawyer—wants to trade $250,000 for a used-car-sized bribe. But that’s exactly what happened when a caller named Jack phoned into “The Ramsey Show,” saying his father offered him $5,000 to sign away future rights to a trust left by his late grandfather.
The catch? Jack isn’t even supposed to get the money until his dad passes away.
“My grandfather had passed away about five years ago and he left a trust to his three children,” Jack explained. “But for my dad, he’s been historically bad with money. So instead of getting a lump sum like his siblings, he receives annual payments. And when he passes away, I’m set to receive the remaining lump sum.”
Don’t Miss:
That lump sum, according to Jack, is estimated to be between $250,000 and $300,000.
But instead of sticking to the plan, Jack’s father wants it all now—and is trying to rewrite the family legacy with a quick cash offer and a renovation wishlist.
“He wants me to sign a document that releases the trust to him,” Jack said. “And he’s bribing me with $5,000 upfront.”
Ramsey couldn’t believe it.
“So you’re going to trade $300,000 for $5,000? What planet does he live on that he thinks you would do that?” he said.
Jack clarified that the offer actually started at $10,000 but was downgraded to $5,000. “He said he wants to renovate his house and buy a new car,” Jack added.
Trending: Have $100k+ to invest? Charlie Munger says that’s the toughest milestone — don’t stall now. Get matched with a fiduciary advisor and keep building
Co-host Ken Coleman jumped in to press for more detail: “You’ve used two words with us—you said ‘threatened’ and ‘bribed.’ What does that actually look like?”
Jack admitted it wasn’t a threat, but a clear attempt at a low-ball buyout.Â
Ramsey shook his head at the logic. “The math is not mathing,” he said. “He’s so illogical that he actually believes you would trade $5,000 for $250,000. That’s just bizarre to me.”
Then Ramsey cut straight to the emotional core of the call.
“There’s no way you can frame a ‘no’ that this guy’s going to like,” he told Jack. “It’s like petting a crocodile and going ‘nice crocodile’—you’re still going to get your arm bit off.”
Then Ramsey told him something that, sure, might come off a little harsh — maybe even offensive — but it was a reality Jack needed to hear: “I wish I could make you have a good dad, but you don’t.”
Ramsey told Jack he’s not just dealing with an unreasonable request, but an unreasonable man—and there’s no tidy conversation that can fix that.
“This guy is going to go bonkers when you say no,” Ramsey warned. “Anything less than bonkers, we’ll call it a bonus.”
See Also: An EA Co-Founder Shapes This VC Backed Marketplace—Now You Can Invest in Gaming’s Next Big Platform
Coleman likened the situation to surgery: “It’s not fun. It’s going to hurt. But on the other side, you’re going to be better.”
The advice wasn’t just emotional—it was tactical. Ramsey urged Jack to keep the boundary conversation short, clear, and free of any guilt-soaked explanations.
“Dad, Grandpa put this in place and I’m going to abide by Grandpa’s wishes,” Ramsey advised Jack to say. “Thanks for asking. I’m sorry it doesn’t work for me. I hope you find another way to renovate your house and get a car—since you’re a lawyer and all.”
Jack, to his credit, had already made up his mind. He wasn’t going to hand over the money. But like so many callers to Ramsey’s show, what he really needed was the playbook for setting a boundary with someone who doesn’t respect boundaries.
“You preserve your dignity, your courage, your kindness, your integrity,” Ramsey told him. “That’s the only thing you have control over.”
And if the call proved anything, it’s that sometimes financial wisdom means knowing when not to sign on the dotted line—especially when someone’s trying to trade your inheritance for a paint job and a new Lexus.
Read Next: Deloitte’s #1 Fastest-Growing Software Company Lets Users Earn Money Just by Scrolling — Accredited Investors Can Still Get In at $0.50/Share.
Image: Shutterstock
