Trump’s Long Game: Buy the Dips, HODL, and Win Big
By Shayne Heffernan
I’ve been around the markets long enough to know a thing or two about playing the long game, and let me tell you—Donald Trump is doing exactly that. Say what you will about the man, but he’s got a knack for keeping everyone guessing while quietly setting himself up for the win. If you’re paying attention, his moves right now are a masterclass in strategy, and there’s a clear takeaway for investors: buy the dips, HODL, and don’t let the noise shake you out.
Let’s break this down. Trump’s been in the spotlight for decades—real estate, TV, politics, you name it. He thrives on chaos, but if you look past the headlines, you’ll see he’s always got an endgame. Right now, with the 2024 election cycle behind us and his influence still looming large, he’s positioning himself as a kingmaker in the Republican Party while keeping his business ventures humming. The man’s not just reacting to the moment; he’s thinking three steps ahead. That’s the long game I’m talking about.
Take his recent moves with Truth Social and the broader media landscape. The stock (DJT on NASDAQ) has been a rollercoaster—up 50% one day, down 20% the next. Classic volatility. But here’s the thing: every time it dips, you’ve got a chance to buy in. I’ve been watching the charts, and the pattern is clear—people panic-sell on bad news, but the core value of Trump’s brand doesn’t budge. He’s got a loyal base, and that’s not going anywhere. So when the market freaks out over some new lawsuit or political drama, I’m grabbing shares at a discount. HODL through the storm, because Trump’s not done yet.
This isn’t just about Truth Social, though. Look at the bigger picture. Trump’s playing a long game with the economy, too. He’s been vocal about crypto—Bitcoin in particular—saying he wants the U.S. to be the “crypto capital of the world.” That’s not just talk. His family’s already dabbling in digital assets, and there’s buzz about a Trump-backed token or NFT project. I’ve been in the crypto space since Bitcoin was under $1,000, and I can tell you, when someone like Trump starts throwing his weight behind it, you don’t want to be on the sidelines. Bitcoin’s at $80,000 as I write this in March 2025, but it’s had its dips—down to $65,000 just last month. I bought that dip, and I’m holding. Trump’s betting on crypto’s future, and so am I.
The strategy here isn’t rocket science, but it takes guts. Markets are emotional—always have been. When Trump says something polarizing, or when the media spins a new narrative, you’ll see fear drive prices down. That’s your moment. Whether it’s DJT stock, Bitcoin, or even some of the real estate plays tied to Trump’s name, the dips are where you make your money. But you’ve got to HODL—hold on for dear life—because the long game is where the real gains are. Trump’s not building for next week; he’s building for the next decade.
I’ll give you an example from my own portfolio. Back in 2020, when Trump was still in office, I picked up some shares in a REIT tied to one of his properties. Everyone said it was a terrible bet—COVID was raging, and commercial real estate looked dead. But I knew Trump’s brand has staying power. Sure enough, by 2023, that REIT was up 40%. I bought the dip, held through the panic, and came out ahead. That’s the playbook I’m using now, and it’s the same one Trump’s following in his own way.
Now, a word of caution: this isn’t for the faint of heart. Trump’s world is a wild ride—legal battles, political firestorms, you name it. If you’re going to play this game, you need to stomach the volatility. Don’t check your portfolio every day; it’ll drive you nuts. Set your buy points, stick to your plan, and let the long game play out. Trump’s been counted out a hundred times, and he’s still here. That’s not luck—that’s strategy.
So here’s my advice: watch Trump closely, but don’t get caught up in the daily drama. When the market overreacts, that’s your signal to buy. Whether it’s his media ventures, his crypto push, or even the broader economic policies he’s influencing, there’s opportunity if you’re patient. Buy the dips, HODL, and let Trump’s long game work its magic. I’m betting on it—and I’ve got the track record to back it up.
