Charlie Woods spent three consecutive years trying to qualify for the U.S. Open. This April, he came closer than ever, but it still was not enough. So on Monday, he settled for the next best option. He walked 36 holes at BallenIsles Country Club, carrying the bag for his future college teammate.

Brentley Romine of Golf Channel reported that Charlie is caddying for his direct competitor, Miles Russell, on the final day of the US Open qualifier. Russell, the world’s top-ranked junior, entered golf’s longest day as one of the most-watched names, along with Matthieu Pavon, Kevin Tway, Luke Clanton, and Matt Kuchar.

In the first round of the final qualifier, Russell shot 71. He carded three birdies on the front nine, and then on the back nine, he picked up 2 more. With the second round still underway, and a projected cutline set at 3 under, how Miles will do remains to be seen.

But overall, it seems having Woods on the bag is helping Miles, and why shouldn’t it? Charlie has substantial knowledge of the qualifier. Just six weeks earlier, on April 28, Charlie Woods was on the other side of the equation.

His own bid for the 2026 U.S. Open qualifying round ended just one stroke short of a playoff after carding an even-par 72 at Eagle Trace Golf Club in Coral Springs.

Charlie had opened the round with a bogey on the first hole before settling into his round. He birdied the par-4 sixth to return to an even par, but a costly double bogey on the par-3 seventh proved very difficult to overcome. He made the turn in 38, continuing the round with birdies at the par 5-10th and the par 4-12th holes as he briefly put himself back into contention. But a bogey on the 14th interrupted the charge, but then a birdie on the 15th was helpful. He then parred his final three holes to finish 10th.

Before 2026, Woods’s previous two attempts at the US Open qualifying weren’t successful. In 2024, he shot 81 at the Legacy Golf & Tennis Club, and then in 2025, he carded 75 at Wellington Golf Club and was seven strokes off the required score.

Apart from this agonizing loss, Charlie’s 2026 season has been average. His best finish was a tie for 19th at the Junior Orange Bowl International in January. He later finished 68th at the AJGA Simplify Boys Championship and then 36th at the Junior Invitational at Sage Valley.

In fact, just weeks before the U.S. Open qualifying, Charlie Woods finished T42 at the Terracotta Invitational. Just this month, he qualified for the U.S. Junior Amateur for the third time. He shot a 3-under 68 and won the sudden-death playoff to get the qualifying spot from the Heathrow Country Club.

Now, as far as Russell’s run goes, he has made history by becoming the youngest player to ever make a Korn Ferry Tour cut and broke Tiger Woods’ record as the youngest AJGA Rolex Junior Player of the Year in 2023. For him, this is one of the final hurdles to becoming one of the greatest young golfers, and for Charlie, caddying for him is a front-row seat to the stage where he almost reached his goal.

Charlie Woods and Miles Russell are the unexpected duo on the ground

The two future Seminoles are well acquainted with competition against each other. They’ve played together at the Junior Invitational at Sage Valley, where Russell beat Charlie by 41 shots and walked away with the famous golden jackets. Charlie, who finished last, went straight to Instagram to congratulate his future teammate.

“What an honor to compete at the Junior Invitational at Sage Valley, a really incredible event. Huge congrats to my friend and future teammate, @milesrussellgolf, on the win,” he wrote.

The golf world tends to see them as rivals, but both of them have committed to Florida State’s golf program for the 2027 season and are future teammates. Their admission is giving FSU coach Trey Jones some of the best-ranked juniors in the country in the same recruiting class.

They were even seen practicing together in February 2026. Clearly, the two are friends as well; otherwise, Russell would not have trusted Charlie to be on the bag as the former chases his maiden US Open appearance. Now, whether Russell makes it through BallenIsles or not and pushes his ticket to Shinnecock remains to be seen, but Charlie has shown how a disastrous loss can turn into a big opportunity if an individual knows how to use it to their advantage.