ESCAPE NEW YORK’S TAX TRAP: Why Texas & Florida Are Pit Stops — The Cayman Islands Is Your True Home
By Jen Philpott
Broker/Owner, Shoreline Properties Cayman Islands
(A Pennsylvanian Living Tax-Free in the Cayman Islands Since 1999)
A large percentage of New York’s top earners are quietly planning their exit.
Money is mobile. So should you be.
Here’s the playbook they’re using — and the one destination that changes everything.
The Crushing Cost of Staying in New York
You didn’t build your wealth to watch it vanish.
- Combined state + city income tax: 14.776% on income over $50K
- 2025 threat: Proposed 2% ultra-millionaire tax pushes top rate to 16.776%
- Wealth tax looming: Bills targeting assets over $50M
- Mass exodus confirmed: 120,000+ fled in 2025 — costing NY $14B in lost revenue
With Zohran Mamdani’s shocking mayoral win on November 5th, the floodgates are opening wider. Billionaires like Bill Ackman poured millions to stop him—now they’re packing for Florida, the Carolinas, and beyond. Wall Street is buzzing: “The Mamdani Effect” has suburban bidding wars in overdrive and luxury listings spiking 15% overnight.
Staying isn’t loyalty. It’s surrender.
- Texas & Florida: Nice Try — But Not Enough
- Zero state income tax? A start.
- Lower property taxes? Helpful.
- But you’re still chained to the IRS.
- You’ll file Form 1040 every year.
- You’ll pay federal capital gains.
- You’ll leave 40%+ of your estate to the government.
- Texas and Florida delay the bleed.
- They don’t stop it.
The Cayman Islands: Where Your Money Finally Works for You
I moved here in 1999.
In 2024, I renounced U.S. citizenship.
I’ve never looked back.
“I was done feeding a system that no longer served me. My money now works for me — not Albany, Harrisburg, or Washington.”
The Tax Reality
- $0 income tax
- $0 capital gains tax
- $0 estate or inheritance tax
No phase-outs. No loopholes. No expiration date.
This is permanent financial freedom.
Life in Cayman: The Upgrade You Didn’t Know You Needed
Winter in New York: 5 months of slush, salt-stained boots, and 19°F wind.
Winter in Grand Cayman: 82°F, barefoot breakfast on the beach in January.
NYC Safety: High crime, locked doors, and constant vigilance.
Cayman: Safer than most U.S. suburbs.
NYC Networking: $18 martinis in a crowded Midtown bar.
Cayman: Sunset rum punch with hedge fund neighbors and happy tourists on the sand.
NYC Office view: High-rise cubicle overlooking concrete.
Cayman: Zoom from your balcony—ocean optional.
This isn’t retirement. This is elevation.
Your New York → Cayman Playbook (Start Today)
You don’t need to renounce citizenship to win.
But for a full reset, follow this sequence:
- Book Your Recon Trip
Direct JFK → GCM flights daily. Stay 5 days. Fall in love. - Meet the Local Experts
Cayman CPA + attorney. Pre-move structuring saves money. - Pick Your Residency Path
Remote Worker Visa: $100K income proof → 2 years (renewable)
Global Citizen Concierge:
$1.45M in real estate → Permanent Residency in 3 years
$2.4M → Immediate Permanent Residency - Exit NY Assets Now
Sell before the wealth tax passes. Time is your leverage.
The Truth No One Says Out Loud
Your money is already global.
It flows through offshore accounts, LLCs, and trusts.
Why are you still stuck in a high-tax cage?
Money is mobile. So should you be.
The Bottom Line
Texas and Florida are pit stops.
The Cayman Islands is home.
I’ve guided 200+ professionals to tax-free living and the perfect property since 2005.
Ready to claim your tax-free future? Drop “CAYMAN” in the comments — I’ll DM you my Cayman Buyer’s Guide and answer your top 3 questions personally.
Your next chapter starts with one message — and I’d love to help you write yours.
Jen Philpott
jennifer@shoreline.ky
+1.345.517.1978