Bobby Witt Jr.’s Shocking Problem: $289 Million Baseball Contract And Can’t Get Enough Marriott Points

I see claims all the time in social media that ‘if you’re rich you don’t care about points’. That isn’t true. There are people who don’t care about points, but I’ve known plenty of wealthy people who do. I’ve helped centimillionaires several times over maximize their points and book award travel. And I’ve helped Hollywood celebrities do it, too.

Plenty of wealthy people become rich by not leaving value on the table. While there are people who appear to light money on fire, that stereotype certainly isn’t generalizable.

Although in my experience it’s people who are well off that run in circles with the truly wealthy who often value points the most. Hollywood B and C-listers can travel like A-listers without the blockbuster deals. They may not be able to buy first class long haul airfare, but they can redeem their points for it. I’ve done that for recognizable actors, directors, and screenwriters.

Bobby Witt, Jr. – who received an 11-year $289 million contract extension this year – stays under an assumed name for security. And the frustrating this about that for him is that it means Marriott won’t let him earn the points. (HT: @roniwalakandou)

Dave Portnoy, who claims a nine figure net worth, brags to a CVS cashier about having 44 million Membership Rewards points.

The top person in the U.S. Membership Rewards program at one point had over 120 million points. And a single transaction earned 2 billion Membership Rewards points in the Hong Kong program (while that’s a large number it’s not actually as big as it sounds given inflated earning and redemption rates in that program). Still, while the transaction was probably laundering money out of China they didn’t mind earning the points.

In a sense 44 million points makes Portnoy a piker, arning them with an Amex Black Card, generally at a single point per dollar spent. While Dave Portnoy calls himself ‘master of points’ simply by virtue of having a lot, he’s hardly maximizing his earn. I have to respect Witt more. He’s not choosing Marriott (though he probably has enough juice to sway the team). But if he’s going to stay at Marriott he wants his points and status.

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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Comments

  1. I’m pretty sure the MLB CBA gives suites or at least upgraded executive rooms. Also thought they could only stay in 4 or 5 star properties (I know the NBA has that but less people traveling for them). Also not uncommon to include upgraded travel requirements in contracts. If room is paid by the team I doubt he would get any points in any event.

    Now if personal travel and using assumed name that is a different story

  2. I wonder if he can take necessary work expenses off of his taxes since he is using an assumed name.

  3. “Although in my experience it’s people who are well off that run in circles with the truly wealthy who often value points the most. Hollywood B and C-listers can travel like A-listers without the blockbuster deals. They may not be able to buy first class long haul airfare, but they can redeem their points for it. I’ve done that for recognizable actors, directors, and screenwriters.”

    This certainly strikes me as being true. Also, I have noted that people who begin young in this miles/points game and have the points maximization game as a big interest when they start in high school or college have turned out to more likely to be the folks who end up buying the $3-10 million homes than their friends and family or even classmates who didn’t have the same interest.

  4. jns, the name on the folio need not match taxpayer’s legal name for IRS purposes. The auditors accept the folios as proof of expense pretty easily when the charges are being paid for by the person expensing the room costs. For proof of the latter, it helps to have all the charges on a bank card account of its own and showing that account being paid by the party legitimately expensing the costs for tax purposes.

  5. one of my closest friends is almost certainly a centimillionaire but was raised to be low key with her money by her low key parents. she actually uses points and miles as a way to downplay her wealth – whenever someone asks her how she affords so many nice vacations or flights she always attributes it to points. now it is true that she often redeems for J and F flights or 5-star hotel stays but she just as often pays out of pocket (she has never flown coach in the time ive known her) whenever there isn’t award space available suitable for her schedule

  6. @Gary “Hollywood B and C-listers can travel like A-listers…” True Hollywood A listers (Oprah, Tom Cruise, Leonardo DiCaprio,…) are traveling by private jet with their entourage and not staying in hotels by private residences. Flying F on AA or stay at the Ritz Carlton isnt the same thing.

  7. The wealthiest entertainment “A-listers” just travel quite differently than a lot of the other “A-list” celebrity entertainers, but it also depends on other factors. If the person is staying in the middle of nowhere outside proverbial Timbuktu for an extended filming period but then the actor-producer suddenly has to bail back to home, it could well be that the helicopter and its pilot stayed around while the chartered or private jet (or the plane pilots) didn’t, and so they hop on the chopper to a commercial airport and then fly back commercially on fixed wings for some reason or another.

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