The first watch Rick Ross ever bought was a Geneva that he picked up for $4,500 at Miami’s 183rd Street Flea Market back in 1998. In the 28 years since, the rapper’s purchases have become increasingly extravagant as his personal fortune and clout continue to grow and the collecting bug takes hold. The Boss showed Robb Report his treasure trove of multimillion-dollar timepieces in 2024, but he has added even more grails since then.  

Ross recently sat down with Robertino Altieri, the CEO and founder of L.A.-based dealer WatchGuys, at his Miami hangar to talk through his favorite pieces—in front of his $35 million private jet, no less. The hip-hop mogul obviously has no shortage of rarities to showcase, with his collection now estimated to be worth several million. (WatchGuys say around $10 million.) He ultimately selected 20 standouts spanning more than two decades. “I brought out the pieces that really had a story to tell you,” Ross says.

He starts by showing off a Rolex Day-Date (Ref. 18038) from the late ‘80s. “Out of all the time pieces that I brought out today, this one means possibly the most to me, and really is the least valuable when it comes to a price,” he explains. It was one of the first watches Ross purchased as a young artist, picking it up for $12,000 back in 2006. He spent his time customizing it with a jeweler, slowly adding diamonds to the case and bezel and Roman numerals to the red dial as more hard-earned dollars came in. In that way, the watch represents his journey from a relatively unknown name to a megawatt star, making it more important to him than some of his other, more expensive pieces. “The price does not determine what it means to you,” he adds. 

At the opposite end of the spectrum is one of six Jacob & Co. watches owned by Ross. The custom Mystery Tourbillon, worth $1.5 million, reflects both the evolution of his taste and the deepening of his pockets. The beautiful 50 mm behemoth is not only covered with white diamonds and gorgeous green tsavorites, but also houses an elaborate movement with not one but two tourbillons. That Ross owns a dozen Jacob & Co. creations, including a Billionaire III worth $3 million, underscores his penchant for the technically advanced and unapologetically lavish. 

“When it comes to timepieces, there’s not a timepiece that’s out of my price range,” he notes. 

Ross isn’t afraid to put his own spin on the classics, either—purists be damned. He points out a Rolex Submariner (Ref. 16613) that he customized with a black diamond bezel. “Oh man, it’s so horrible now that I look at it,” he laughs. “You see, that’s the fun thing about just being creative. You do some shit, and you look back at it now like, yo, that watch horrendous.” 

Half the watches Ross brought to showcase are Rolexes. There are six Day-Dates, including one that pairs a coveted stone dial with an ostentatious aftermarket bracelet that has been nicknamed the “gold nugget,” and another that features a sought-after meteorite dial. 

His newer additions include two pieces by Avi & Co. The family-owned watch and jewelry retailer is known for selling Pateks, Audemars Piguets, and Rolexes, but has started making diamond-encrusted timepieces in the past couple of years. Ross seems particularly fond of a frosted rose-gold piece he has nicknamed the “glazed donut.” “This is the first piece I ever bought from them,” he recalls. “Just because I loved the frost that was on the band. I was like, I don’t have anything like that. I want it.”

Making up the rest of the 20 are a couple of custom APs, two Hublots—one of which was given to him by none other than Dr. Dre—and a skeletonized Cartier Santos that has been given the blingy Boss touch. “See, my mom, since I was young, always spoke so highly of Cartier,” he says. “That was like her brands, Louis Vuitton and Cartier, so I’ve always had an affection for Cartier. And when I found out I could get it blown all the way out like that, I needed it.”

As for his daily beater, Ross says he switches it up depending on his outfit and mood. “I don’t have a favorite everyday watch because my vibe changes, you know,” he adds. He is wearing an iced-out Patek Philippe Nautilus 5719/10R-010 during the interview. That reference alone can fetch $800,000 on the secondary market, underscoring the caliber of Ross’s ever-growing collection and his enduring big, bold style.

WatchGuys will share the full podcast interview with Rick Ross on Saturday, March 21.

Click here to see more photos of Rick Ross’s watch collection.