Drake's Insane Multi-Million Dollar Watch Collection

This is one of the rarest watches in Drake's entire collection. The Daytona "Asprey" is a confirmed collaboration between Rolex and British jeweler Asprey, featuring a turquoise dial signed by Asprey beneath the Cosmograph text and a matching turquoise gemstone bezel set into an 18k white gold case. The piece sits on a white gold Oyster bracelet. These references were never produced in any meaningful quantity, and Drake's example is one of very few known to exist anywhere in the world. It remains the headline piece of his collection.

Drake's pink Daytona is one of the most photographed pieces in his arsenal. The 18k yellow gold case carries a pink baguette gemstone bezel framed by diamond-set lugs, a pink dial with matching subdials, and a soft pink alligator strap. The watch surfaces regularly across his social posts, including the now-famous "Life Is Short, Party Hard" tee photo. Custom Daytona configurations of this depth are not catalogue Rolex, they are factory-modified pieces commissioned through select boutiques and they command serious premiums on the secondary market.

The Rainbow Daytona 116595RBOW is the Everose gold reference with a rainbow sapphire baguette bezel, diamond-set lugs, and a pavé diamond dial with chronograph subdials in matching rose gold. The bracelet is fully diamond-set across center and outer links, finishing one of the most heavily commissioned configurations Rolex has ever offered at the boutique level. Drake's example is photographed in low light against a tie-dye backdrop, the gradient sapphire bezel catching exactly the kind of color play this reference was designed to produce. The Rainbow has been discontinued and reaches well into six figures on the secondary market.

The Paul Newman Daytona is the watch that transformed Rolex into a collector's brand. Reference 6239 was produced in tiny numbers across the 1960s, with an exotic Art Deco dial that was largely overlooked at retail and only later understood as one of the most important configurations in modern watchmaking. Drake's example surfaces with him courtside at Toronto Raptors games, paired with vintage denim. Original-condition Paul Newman pieces have crossed the seven-figure mark at major auction houses, and the 6239 reference is the configuration that started it all in 1963.

The Daytona reference 116578SACO is a factory gem-set configuration in 18k yellow gold with an orange sapphire baguette bezel and a white mother-of-pearl dial set with diamond hour markers. Drake wears it in one of the most circulated photos of his style, paired with a Princess Diana "England's Rose" tribute t-shirt. The orange-on-yellow-gold contrast and gem-set bezel push this beyond the catalogue gold Daytona, into the category of factory-modified configurations that Rolex builds in extremely limited numbers for select clients across the world.

The Daytona reference 16568TBR is a yellow gold zenith-era piece with baguette diamond bezel, ruby hour markers, and a fully pavé diamond dial set with mother-of-pearl chronograph subdials. The watch dates to the late 1990s era of Rolex collaboration with Zenith for the chronograph movement, predating the in-house caliber 4130. Drake's example surfaces on his wrist over a textured throw, the rubies and pavé diamonds catching ambient light. Vintage gold Daytona pieces with full gem-set configurations are increasingly difficult to source in original condition, especially with the original ruby and diamond layout intact.

Nicknamed the "Giraffe" by collectors, this Everose gold Daytona reference 126555TBR features a brown lacquer dial with a custom giraffe-print pattern across the chronograph subdials, a fully baguette diamond bezel, and diamond-set lugs. The watch is paired to a brown Oysterflex strap, finishing one of the most aggressive custom Daytona builds Drake owns. Photos with this piece flood his Instagram, often with the watchguys.com tag still visible on the dial. Aftermarket factory builds at this level are not standard catalogue items, they sit in their own tier of the Rolex universe.

The 116576TBR is the platinum Daytona with a fully pavé diamond dial, applied diamond hour markers, baguette diamond bezel, and the standard platinum Oyster bracelet. Drake owns this reference in multiple dial executions, including an ice blue pavé and a chocolate-toned pavé variant photographed inside its presentation case. Platinum Daytona references are produced in extremely limited annual quantities, and the gem-set dial variants are even more restricted. The 116576TBR sits at the top of the platinum sport-chronograph segment, with retail pricing that exceeded $200,000 even before any secondary market premium.

The 126538TBR is the 18k yellow gold Daytona with a fully baguette diamond bezel, champagne sunburst dial set with baguette diamond hour markers, and matching baguette diamond lug accents on an Oysterflex strap. Drake's example surfaces in a candid moment with the watch in clear view, the warm gold and champagne tones reading classically restrained against the heavy gem setting. Yellow gold baguette bezel configurations remain among the most-requested factory modifications in the Daytona catalogue, particularly with the rubber strap option that keeps the visual weight of the case fully on the dial and bezel.

The platinum Daytona reference 116506 has earned the nickname "Platona" among collectors. Drake's example carries the standard ice blue dial with chestnut brown Cerachrom bezel and platinum bracelet, fitted with a baguette diamond hour marker configuration. Released to celebrate the 50th anniversary of the model, the 116506 was originally produced in limited numbers and reserved for top Rolex clients. The discontinued status, paired with the platinum case and chestnut Cerachrom bezel, has driven this reference well above retail on the open market in recent years.

The yellow gold Daytona 116508 with green dial earned its "John Mayer" nickname after the musician championed the reference on the Hodinkee "Talking Watches" episode. Drake wears the watch frequently with his everyday gold chains and casual fits. The combination of the 18k yellow gold case, sunburst green dial, and matching Oyster bracelet became one of the most-requested Daytona configurations on the secondary market, with values rising sharply after the John Mayer interview aired. The reference was discontinued in 2023, further pushing market values upward.

The 228396TBR is the 40mm platinum Day-Date with full baguette diamond bezel and ice blue dial. Drake pairs the watch with diamond bracelets courtside at Toronto Raptors games, where it picks up cameras every time he checks his phone. Ice blue dials are reserved for platinum Rolex models exclusively, a tradition the brand has held since the metal first entered the catalogue in 2002. The 228396TBR sits at the top of the modern Day-Date hierarchy from a metal and gem-setting standpoint, retailing well into six figures even before secondary market premium.

The 36mm Day-Date 128234RBR comes in 18k yellow gold with a diamond-set bezel and a genuine turquoise stone dial. Drake has been spotted in this piece courtside at NBA games, shouting at officials with the watch fully exposed on the wrist. Stone dials remain among the most collectible Day-Date configurations, with turquoise sitting alongside opal, lapis, and onyx as the most desirable variants. The 128234RBR is the modern interpretation, with the 36mm proportions Rolex returned to in the latest generation of the President.

The 228398TBR is the 40mm yellow gold Day-Date with a baguette diamond bezel and champagne sunburst dial set with baguette diamond hour markers. Drake wears the watch in casual neutrals, photographed in a park with linen pants and an off-white tee, the gold case catching the sun against the soft tones. The combination of the warm champagne dial and matching gold case across a heavily gem-set bezel is the textbook configuration for a "classic" modern President with maximum jeweled presence. The 228398TBR is the gem-set sibling to Drake's standard 228238 Day-Date.

The white gold Day-Date 128349RBR features a pink dial set with diamond Roman numerals, a fully diamond-set bezel, and a diamond-paved President bracelet. Drake's photo with this piece, throwing up a finger to the camera courtside, became one of the most reposted watch shots on his timeline. Pink dials remain rare in the official Rolex catalogue, particularly in white gold, and the diamond-set bracelet places this watch at the top of the configurable Day-Date 36 menu, with retail pricing exceeding most catalogue gold sport models.

The 40mm yellow gold Day-Date 228238 is the closest thing Drake owns to a "classic" President. Champagne dial with diamond hour markers, fluted bezel, and the standard President bracelet, all in 18k yellow gold. Drake has worn this piece across years of OVO content, including with his Toronto Raptors championship ring at the Essentials hoodie launch. The 228238 is the catalogue 40mm President at retail, and the most accessible (relatively speaking) entry into Drake's Day-Date rotation, sitting beneath the gem-set and platinum references in this section.

The Sky-Dweller 326959TBR is the white gold annual calendar GMT, fully iced out across case, lugs, bezel, and bracelet with baguette diamonds. The white silvered dial retains the rotating ring command bezel function and the second time zone disc at the dial center, both engineering signatures of the Sky-Dweller line. Drake's example is photographed at home with diamond chains and the watchguys.com tag visible on the dial. Fully gem-set Sky-Dweller configurations are rarely produced, and white gold examples are among the rarest references in the entire Sky-Dweller catalogue.

The GMT-Master II reference 116758SANR is the 18k yellow gold version with sapphire baguette and diamond bezel and matching diamond-set crown guard. Drake wears it with a black dial and gold Oyster bracelet, photographed at home over candlelight with his "Care Package" album artwork in the background. Factory gem-set GMT-Master II configurations are produced in extremely limited numbers, and the 116758SANR sits at the top of the diamond-set GMT lineup. Once discontinued, secondary market values on this reference doubled almost overnight.

The Yacht-Master 226668TBR is the 42mm yellow gold reference, factory configured with baguette diamond bezel, diamond-set lugs, pavé diamond dial, and matching rubber Oysterflex strap. Drake's example surfaces in a candid wrist shot in jeans and a denim jacket, the watch reading less formal than its specification suggests. Diamond-set Yacht-Master references are an uncommon factory commission for Rolex, particularly the full pavé dial configuration in solid gold. The 226668TBR sits among the most heavily jeweled current-production sport models in the entire Rolex catalogue.

This Pearlmaster Datejust reference 86348SABLV is 18k yellow gold with a rainbow sapphire bezel, diamond-set bracelet links, and a pavé Roman numeral dial. Drake wore the watch in a "Wait Till U See My..." tee in the now-circulated palm tree photo. The Pearlmaster line is Rolex's most heavily jeweled Datejust offering, and the 86348SABLV with rainbow gradient is one of the rarest configurations the brand officially produces. These are not catalogue pieces in the standard sense, they are commissioned through select boutiques on extended waiting lists.

The 5719/10R-010 is the 18k rose gold Nautilus with full baguette diamond bezel, baguette-set bracelet, and a fully diamond pavé dial with diamond-set baton hour markers. Drake's example surfaces courtside at a Toronto Raptors game, paired with a denim jacket and shearling collar where the warm rose gold case picks up arena lighting on every camera cut. The 5719 series is the gem-set production line of the Nautilus, made in extremely limited quantities and reserved for select Patek Philippe clients. The rose gold variant remains the rarest of the metal options for this reference.

The white gold counterpart to Drake's rose gold 5719, the 5719/10G shares the full baguette diamond bezel, baguette-set bracelet, and pavé diamond dial layout, executed entirely in 18k white gold. Drake wore the watch with a Bob Marley printed shirt at a public appearance, where the dial flash dominated the frame on every photo. Owning both the rose gold and white gold variants of the 5719 in parallel is a flex specific to top-tier Patek collectors. Fewer than a handful of these pieces enter the secondary market in any given year worldwide.

The 5740/1G is the Patek Philippe Nautilus Perpetual Calendar in 18k white gold, the thinnest perpetual calendar Patek has produced inside the Nautilus case. The blue dial with day, date, month, and moonphase apertures retains the Nautilus horizontal embossing despite the complication-heavy layout. Drake wore it for a red-carpet appearance, paired with an OVO tie-dye hoodie. The 5740/1G replaced the legendary 5712 at the top of the Nautilus complication ladder and has held a long retail wait list since launch.

This is one of the most discussed pieces of custom watch work of the past decade. Reportedly customized in collaboration with the late Virgil Abloh, Drake's all-green Nautilus features full emerald baguette setting on the bezel, case sides, and bracelet, plus a fully gem-set green dial with moonphase and date apertures retained. The watch surfaces in Drake's video work and certain walk-in interview clips. Because the piece is one-of-one with no formal market comparison, market value remains undisclosed. Pieces of this customization tier rarely if ever change hands publicly.

The Richard Mille RM 69 "Erotic Tourbillon" is one of the most unusual pieces in Drake's rotation. The titanium tonneau case houses three rolling cylinder displays that spell out provocative phrases, paired with a flying tourbillon at six o'clock visible through a generous skeleton aperture. Drake debuted the watch courtside at a Toronto Raptors playoff game, where the rolling text drew immediate attention from broadcast cameras. Limited to a total run in the dozens, the RM 69 is one of the rarest and most provocative references Richard Mille has ever released.

The Astronomia Casino reference AT160.40.AB.AB.B is a triple-axis tourbillon with a fully functional miniature roulette wheel built into the dial. Drake's example is the rose gold version, with a red, black, and green roulette wheel that spins on demand at the press of a pusher. The watch was photographed at his casino-themed event, paired with a fur-collared coat. Jacob & Co produces fewer than ten Astronomia Casino pieces in any given configuration, and the rose gold version is one of the most graphically aggressive watches in Drake's entire rotation.

The Jacob & Co Five Time Zone is the watch that put Jacob the Jeweler on the map in hip-hop. The 47mm case displays five separate dials, each tracking a different time zone, set against a pavé diamond background and framed by a diamond bezel. Drake has been photographed in multiple strap configurations, including a vivid yellow crocodile in the "Third Ward" jersey shot and a soft blue alligator variant. The Five Time Zone is the reference that defined Jacob & Co's signature look in the early 2000s, worn by virtually every major figure in hip-hop, and it remains a touchstone piece for collectors revisiting that era.