NFL Hall of Famer — Heisman Trophy Winner — FOX Sports & ESPN Analyst
Charles Woodson's Breitling Flying B: The One That Never Played It Safe
Charles Woodson built a Hall of Fame career by doing things no one expected a cornerback to do. On his wrist: a Breitling Flying B — a discontinued tonneau-cased chronograph from Breitling's most unconventional era, bold enough to polarize collectors and confident enough not to care.
| Charles Woodson. Source: FOX Sports / X |
Breitling Flying B chronograph. |
Charles Woodson was born on October 7, 1976, in Fremont, Ohio, and grew up to do something no one else has managed before or since: win the Heisman Trophy as a player whose primary position was on defense. At the University of Michigan in 1997, Woodson — a cornerback who also returned punts and took occasional snaps on offense — beat out Peyton Manning for college football's most prestigious individual award. The decision was controversial then and remains debated now. Woodson was not bothered. He had spent his college career making plays that defied the conventional logic of what a cornerback was supposed to do, and the Heisman was simply the sport catching up with what he already knew about himself.
The Oakland Raiders took him 4th overall in the 1998 NFL Draft. Over eighteen seasons with Oakland and the Green Bay Packers, Woodson assembled one of the most decorated defensive careers in professional football history: nine Pro Bowl selections, the 1998 Defensive Rookie of the Year award, the 2009 NFL Defensive Player of the Year award, a Super Bowl XLV ring with Green Bay in 2010, and 65 career interceptions — 20 returned for touchdowns, a record that underlines just how different his version of cornerback was from everybody else's. He retired in 2021 and was inducted into the Pro Football Hall of Fame that same year. Since then he has built a wine label, Charles Woodson Wines, and become a familiar presence as an NFL analyst for FOX Sports and ESPN.
The only primarily defensive player in history to win the Heisman Trophy. He did it his way, not the expected way. — Charles Woodson's career in a sentence
Timepiece
Breitling Flying B Chronograph
Breitling, founded in Saint-Imier, Switzerland in 1884, is best known for aviation and dive instruments with round cases and utilitarian DNA. The Flying B was something else entirely: a product of the early 2000s under CEO Ernst Schneider, when Breitling briefly pushed into dress-watch and high-luxury territory with unconventional case shapes. The Flying B's tonneau form — rectangular with curved sides — and its embossed winged "B" logo made it an outlier in a catalog otherwise dominated by round sport chronographs.
Its standout feature is a jump-hour digital display at 12 o'clock: the hour "flies" to the next digit instantaneously rather than sweeping continuously, a complication that suited the watch's theatrical character. The movement is a Caliber 28 — an ETA 2892-A2 base with a Dubois-Dépraz chronograph module. Available in steel, gold/steel, or full gold. Discontinued around 2010, it has since become a collector's curiosity: a piece that Breitling would never build today, from a period when the brand was willing to take real risks with its identity.
| Reference | A28362 / R28362 (steel / gold-steel) |
| Case | Tonneau (rectangular, curved sides); steel, gold/steel, or full gold |
| Movement | Cal. 28 (ETA 2892-A2 + Dubois-Dépraz module); automatic chronograph |
| Market Price | ~$3,000–$8,000 secondary market depending on material |
The Cornerback Who Played Like a Safety, and the Watch That Refused to Be Round
The Breitling Flying B is not a watch that polled well with focus groups. In a catalog built on round aviation chronographs worn by pilots and endorsed by serious tool-watch collectors, the tonneau-cased Flying B with its jump-hour display and embossed winged logo was an act of genuine provocation. Breitling made it because they could, because they wanted to see what happened, and because Ernst Schneider was willing to put Breitling's name on something that departed completely from what Breitling was supposed to be. The watch community's response at the time was mixed. The watch is discontinued. And now — as tends to happen with bold decisions that weren't immediately understood — it is quietly appreciated by the people who actually look.
Woodson spent his career doing the equivalent. Cornerbacks were not supposed to win the Heisman. Defensive players were not supposed to change field position from both sides of the ball. Cornerbacks in their mid-thirties were not supposed to win Defensive Player of the Year and then add a Super Bowl ring. Woodson did all of it, not by ignoring expectations but by making them irrelevant. The Flying B on his wrist is not a coincidence of taste. It is the natural watch for a man who built a Hall of Fame career out of doing things that weren't in the playbook.
A Discontinued Watch for a Player Who Was Never Going to Fit Any Category
The Flying B is now worth more as a conversation than it was as a product. Breitling has moved on; the current catalog is cleaner, more focused, and easier to explain. The tonneau-era pieces are their own thing — artifacts of a moment when the brand was willing to be strange. That secondary-market price range of $3,000 to $8,000 reflects exactly what that kind of courage is eventually worth: not as much as the conventional choices at the time, but far more interesting than anything that played it safe. Charles Woodson's Breitling Flying B earns its place on this wrist for the same reason Woodson earned his Heisman on defense: because someone who was already great decided to do something nobody expected, and it turned out to be exactly right.
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