How Dave Portnoy Can Spend 44 Million Amex Points (2024)

Barstool's Dave Portnoy and His Amex Points Warchest

If you read this site and are between the ages of 14 and 40, you've no doubt seen the now-viral video of Barstool Sports' Dave Portnoy at a Rite-Aid. In the video, Portnoy uses his American Express Centurion Card to make a purchase, and his American Express Membership Reward Point total flashes up on the screen of the credit card reader: 44.4 million American Express points.

The Rite-Aid cashier very earnestly says "you probably could go on a trip!" when referring to how Portnoy should use his points. This got me thinking: how could Portnoy use all of his American Express points? And what would be the best redemption?

Redeeming Amex Points for Cash

Amex Statement Credits - $266,400

Let's start with the all-time worst way to redeem American Express Membership Rewards points: for cash. Given to you in the form of a statement credit, American Express points redeemed for cash have a redemption value of 0.6 cents per point. That's about 1/3 of their actual value when used correctly, so this is a dramatically bad redemption of the points Portnoy worked so hard to achieve. If he were to cash out directly using statement credits, Portnoy would receive about $900,000 on his 44.4 million Amex points.

Spending Amex Points at Rite-Aid - $310,800

Since Portnoy is at Rite-Aid anyway, let's pretend he wants to do all of his shopping there and make purchases directly with his enormous points balance. If he were to do this, he could redeem all of his points for slightly more than taking the standard American Express statement credits, but this video actually provides us with really great information about Rite-Aid redemptions. American Express is pretty vague in their official redemption policy about Rite-Aid, so a quick glimpse of a $1.59 pack of gum being worth 227 American Express points gives us a calculation we can work with. Still not a great one, but at least it's a data point.

Charles Schwab Platinum Brokerage Redemption - $488,400

There is, however, another cash redemption that is much, much better, and that's investable cash. If Portnoy happens to be a Charles Schwab customer (which I don't think he is based on his "Davey Day Trader" video series during the pandemic in which he used E*Trade), he could pick up the American Express Charles Schwab Platinum Card. Thanks to a partnership with Schwab and American Express, this card allows for points redemptions directly into a brokerage account at 1.1 cents per point, a much better redemption option, though still not awesome.

Traveling with Amex Points

Flying Qatar Airways First Class Roundtrip to Doha for the World Cup Final 211 Times

Since Barstool is based out of New York, I'll be using JFK for all of my points calculations, starting with Qatar Airways. Commonly known as one of the best airlines in the sky, their QSuite business class product is the gold standard of international business class. Well, at a standard redemption of 210,000 Avios points for a roundtrip ticket from JFK to Doha, Portnoy could transfer all of his American Express points at a 1:1 ratio and fly in this first-rate business class 211 times!

The Qatar QSuite

Flying Delta One Suites Roundtrip to London 75 Times

This shows how shockingly inefficient flying Delta Airlines can be. The biggest American carrier debuted their first class suite product in 2016 to...mixed review, but it's still one of the nicest seats in the sky if you're based in the U.S. Unfortunately, the Delta SkyMiles program has seen devaluation after devaluation in recent years, meaning you're going to have to pony up around 540,000 Delta SkyMiles at a 1:1 transfer ratio with American Express points to fly in your own suite. However, Portnoy's haul of points mean he could fly from JFK to London Heathrow 75 times roundtrip while only paying taxes on the flights. Incredible.

The Delta One Suite

Flying Singapore Suites to Singapore 180 Times

Again going outside of U.S carriers, we're back into uber-luxury. This time, we're checking out a type of seat that may never be topped: the Singapore Suite. Coming in both a single and double suite, this airline room has a full captain's chair and foldout bed, along with multiple TV screens, fine dining and unbelievable attention to detail. Portnoy could also fly this route from his base in JFK to Singapore 180 times on points alone. According to credit card points veteran Ben Hedges, one roundtrip trek on this route is over $15,000, meaning Portnoy would achieve nearly $3 million in free travel, putting Portnoy's redemption at close to 6 cents per point.

The Singapore Airlines Suite

Spending 3 Years in Paris...or 11 Years in Poland

This is a fun one courtesy of the experts over at The Points Guy. Taking advantage of the transfer system from American Express to Hilton Hotels, Dave Portnoy could move his points to Hilton at a 2:1 ratio and suddenly find himself with nearly 90 million Hilton points. This volume of points could score him free nights at any Hilton property around the world, including the top-class Waldorf Astoria in Paris where he could spend 1,110 nights there for free.

If he really wanted to stretch his points, Portnoy could look at the Hilton Garden Inn in Krakow, Poland, where The Points Guy estimates he could spend a little over 11 years at the property for free.

Booking $900,000 Worth of Amex Travel Portal Trips

So here's one that is truly exclusive to those of Dave Portnoy's level of wealth. Thanks to his owning the American Express Centurion Card, Portnoy gets the unique perk of getting a 50% points rebate on travel booked through the American Express Travel portal. This means that, rather than the 1 cent per point redemption this portal typically provides, Portnoy would instantly unlock a 2 cent per point redemption on effectively any airline he chooses. Not that he'd need it, but he also qualifies for status on those airlines with bookings made in the portal, so he could achieve Delta 360 Status almost immediately.

How Should Dave Portnoy Spend His Amex Points?

The best, quickest and most complete answer I can provide here is: in any way he can. Here's why. In the video, Portnoy declares that he's hoarding points and wants to "die with them." Other than airlines not typically allowing corpses on planes, Portnoy is likely to get hit with devaluations that take him out at the knees on redemption values, so points aren't investments - they're currency.

If it were me, I'm all day taking up the Singapore Suites offer. There's nothing else like it in the sky, and their food is apparently second to none (including the award winning chicken satay skewers).