The Obama Gambit: Why Trump’s Latest Attack Could Destroy Him

How going after Obama turns Trump’s strategy upside down—and hands the Resistance the upper hand

The Obama Gambit: Why Trump’s Latest Attack Could Destroy Him

How going after Obama turns Trump’s strategy upside down—and hands the Resistance the upper hand

The Jack Hopkins Now Newsletter #444: July 24th, 2025

Part 1: The Line He Shouldn’t Have Crossed

Donald Trump has done a lot of reckless things in his political life—things that would’ve sunk anyone else a hundred times over.

But going after Barack Obama?

That’s not just reckless.
It’s suicidal.

It’s a strategic misfire of epic proportions. And if you zoom out for even a second…you can see why:

Obama isn’t just a political opponent.

He’s a cultural force…a global symbol…and to tens of millions of Americans…especially the ones Trump needs to peel off…Obama represents stability…dignity…and hope.

You don’t take a swing at a monument without consequences.

And the boomerang that’s coming?
It’s sharp enough to decapitate a comeback.

Part 2: Trump Just Picked a Fight with America’s Favorite President

Let’s get one thing straight: Barack Obama is still…to this day…one of the most beloved presidents in modern history.

Poll after poll shows his post-presidency favorability towering over Trump’s. Even among independents and moderate Republicans…Obama remains a reassuring symbol of calm competence.

Trump, on the other hand? He’s polarizing even in his own party.

So what happens when the man with the lowest approval rating of his second term goes nuclear on the man with one of the highest favorability ratings in recent history?

He loses the middle.
He hardens his enemies.
And he lights a match on the gasoline-soaked rag of political backlash.

You want to rally Democrats?
Go after Barack Obama.

You want to reawaken Black voters…young progressives…and suburban swing voters all at once?

Attack the one guy they still trust.

Trump didn’t just make a tactical error.

He hit the third rail with both hands.

Part 3: The Democratic Base Was Sleepy. Now? They’re Waking Up.

Here’s a truth most Democrats won’t admit out loud: their base was bored.

Frustrated.
Checked out.
Beaten down by cynicism and infighting.

And Trump just gave them a reason to rise again.

Not just to grumble on social media.
Not just to donate a few bucks.

But to show up.

This move will send a jolt of electricity through every:

• Organizer

• Activist

• Suburban mom

• Black churchgoer

• Young voter

• TikTok creator

• Union worker

He just took the one remaining figure with moral clarity and symbolic resonance…and tried to kneecap him in front of the world.

Bad move.

Because while Democrats can be disorganized…distracted…and sometimes infuriatingly passive….when you come for Obama? They don’t need a memo.

They mobilize.

Part 4: Independents and Moderates Will Snap Out of Their Trance

Let’s talk about the real swing: the middle.

The independents.
The exhausted.
The “I don’t like either party” voters.
The suburban moderates who voted Trump once but felt dirty about it.

They’ve been drifting.
Numb.
Muted by inflation…disinformation…and fatigue.

But Trump going after Obama? That cuts through the fog.

Suddenly, this isn’t politics-as-usual.

This is a vendetta.

A power grab.

A desperate man swinging down instead of rising above.

It’s a move that feels unhinged. And independents hate unhinged.

Even if they’re skeptical of Democrats…they respect Obama.

They remember the calm voice…the scandal-free White House…the love story with Michelle…the poetry in his eulogies.

Trump going after that?

It’s like punching Mister Rogers in the face.

Part 5: He Just Gave Obama the Mic Again

Here’s what Trump doesn’t seem to understand:

When you attack Obama, you amplify him.

You make him relevant again.
You give him a stage, a spotlight, and a cause.

You think Joe Biden giving a speech fires people up?

Wait until Obama starts criss-crossing the country in 2026 and 2028, defending democracy against the man who smeared him.

Wait until he goes viral with a line so devastating it turns into a ringtone for the resistance.

Obama’s been largely quiet.

Now he has moral authority and personal cause.

Trump didn’t wound him.

He resurrected him.

Part 6: The GOP Is Nervous—and They Should Be

Let’s not pretend the GOP is one happy family. Trump’s hold over the party is cracking.

Between the Epstein backlash…criminal trials…and growing calls for younger leadership…his grip is slipping.

By attacking Obama…Trump just gave every squeamish Republican…every donor… strategist…and governor…a brand new reason to distance themselves.

Why?

Because they know it looks racist…desperate…and deranged.

And while MAGA might eat it up…the rest of the electorate will not.

The smarter Republicans see it coming:

• Losses in the suburbs

• Turnout spikes among Democrats

• A bloody midterm for House Republicans

• And a nightmare 2028 cycle they may not recover from

Behind closed doors…they’re already whispering: “He’s going to cost us everything.”

Part 7: This Could Trigger Legal and Political Retaliation

You want to open the floodgates? Go after Obama.

Because once that line is crossed, the gloves come off.

Democrats…long accused of being weak…now have every excuse to go full scorched earth:

• Investigations into Trump’s foreign ties

• Reopening sealed evidence

• State-level lawsuits and subpoenas

• Targeting Trump’s orbit with a level of aggression they’ve avoided until now

Why?

Because when you make it personal…the response gets personal too.

They’ll have cover, justification…and public support.

And that, more than anything…could bury Trump.

Part 8: It Exposes Trump’s Desperation—and the Clock Is Ticking

Why is he doing this now?

Simple: he’s cornered.

The Epstein files are a ticking time bomb.
His trial calendar looks like a doomsday clock.
He’s bleeding independents.
He’s losing grip on the party.
And even his most loyal mouthpieces are hedging their bets.

Going after Obama isn’t strength.
It’s panic dressed in bravado.

It’s what a man does when he’s out of plays and terrified of what’s coming.

But in doing so…he’s started a fight he cannot win.

Because Obama doesn’t need to beat him.

Obama just needs to exist…and let the rest of America remember what decency looked like.

Part 9: He Lit a Fire—and It's Spreading Fast

The smart people know what’s happening.

This isn’t just another Trump tantrum. It’s a strategic collapse in real-time.

The backlash is brewing. And it’s not just Twitter rage or performative outrage.

It’s:

• PACs forming

• Volunteers signing up

• Organizers meeting

• Attorneys networking

• Donors reengaging

• Gen Z creating

• Veterans reactivating

This is bigger than a campaign.
This is a cause now.

Trump lit a fire.

And it’s spreading through every community that ever believed in Obama’s hope and decency.

He thought he’d rally his base.

He may have just rebuilt the Resistance.

Closing: Be Careful What You Swing At, Donald

Trump wanted a target.
He chose wrong.

Obama isn’t weak. He’s waiting.
And now? He doesn’t have to say a word.

Because millions of Americans are ready to speak for him.

With their voices.
With their votes.
And if needed—with a level of resistance that makes 2020 look like a dress rehearsal.

Donald Trump didn't just pick a fight.

He picked his downfall.

I’m inspired. I’m on fire. You have no idea how much I hate the fact that I have to sleep. I want to be doing this 24 hours a day. I do have to get my 7 hours of sleep…and I do, but rest assured..the rest of the time? I’m doing this.

You…me…us? We are absolutely making a difference in this fight. Know that.

I’ll be back soon. You’re strong. You question that sometimes. So what?! It doesn’t change the fact that you are powerful. It. Does. Not.

Warmly,

-Jack

P.S. The smartest insurgencies don’t start with armies. They start with insults…with one unjust move too far. If Trump just kicked off the next great political counterstrike…it won’t be from DC. It’ll come from the suburbs…the college campuses…the church basements…the group chats. And it’ll look like the one thing his movement cannot stand:

Decency with teeth.

We’re about to find out who’s been sleeping…and who’s been sharpening the proverbial “knives.”

Stay close.

More soon.