Bobby Witt Jr.'s contract brings unexpected challenge with Marriott loyalty program

Hollywood celebrities and other well-off individuals often seek ways to travel luxuriously without incurring high costs. "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," said another source familiar with such practices.

Dave Portnoy, who claims a nine-figure net worth, has also been vocal about his accumulation of 44 million Membership Rewards points. Despite his significant holdings, some experts argue that Portnoy could optimize his earnings further.

"The top person in the U.S. Membership Rewards program at one point had over 120 million points," revealed another insider. Additionally, a single transaction once earned 2 billion Membership Rewards points in Hong Kong's program, although this was likely linked to money laundering activities.

In comparison, Bobby Witt Jr.'s efforts to earn Marriott points demonstrate a strategic approach despite his substantial wealth. "I have to respect Witt more," remarked one analyst. "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."