Andrew Bailey is headed to the 2027 U.S. Masters

Andrew Bailey sat on the bed in his hotel room the night of October 1 staring at the trophy. An ornate sterling silver cup, named for golf legend Bobby Jones. He was looking at the Robert T. Jones Jr. Memorial Trophy. That’s when it all hit him. He’d actually done it. He had won the 2026 U.S. Mid-Amateur Championship at Sand Valley in Wisconsin.

“I never knew if I thought this was possible,” he said.

Just hours before he proved it was, beating Nate Smith. Now, he’s headed to the Masters and the U.S. Open in 2027.

Andrew’s golf career has been one of peaks and valleys, for sure.

He came to Cleveland State in 2010 after pairing with Steve Weir, CSU’s men’s golf coach, at the 2009 Ohio Open, the state’s premier golf tournament. He calls it a stroke of luck.

At St. Ignatius, where he attended high school and played on the golf team, he admits he wasn’t the best. He didn’t even make the cut to join the team his freshman year. But at the Ohio Open, Andrew shot a 68 on the par-71 course, 3 under par.

That was a good score for him.

“It was basically that next week, he gave me a call offering me a spot on the team at CSU,” he said.

“So, the rest is history, and one of the best decisions I ever made.”

At CSU, Andrew met Shelly, his future wife and a golfer on women’s team. He also met some of his best friends to this day. When he married, half of their 14-person wedding party were Vikings.

In 2014, the year he graduated, he went pro.

“Kind of being a little naive to the whole amateur game of golf, I thought the only path to playing competitive golf after college was to play professionally,” he said.

But it soon lost its luster. It turns out the juice wasn’t worth the squeeze. The risks far outweighed any reward. And Andrew fell out of love.

Then in 2015, during a rock-climbing trip at Whipp’s Ledges, he fell 20 feet onto a bed of rocks, fracturing his wrist.

That fall “might have been the best thing to ever happen to me,” he told the Associated Press.

He returned to play after he healed but pro golf had exacted a big. enough toll by then. On him and on his relationship with Shelly. So, he quit refocusing his attention on the amateur circuit.

It took time but eventually his love for the sport rekindled, though there was a period he didn’t compete much at all.

In 2018, he started working for Holderness & Bourne, a golf apparel brand, as a sales rep. He would spend 120 nights a year on the road, convincing golf courses throughout the Midwest to carry its merchandise. It was a fledgling company at the time, with only 20 customers, so the hustle was real.

Along the way, his interest in golf architecture grew. How courses link tees, fairways and greens. How the landscape and topography, the elevation and bodies of water, the soil and vegetation form wholly natural spaces. How sand traps provide augment design and help guide players. This and more.

When Andrew realized that playing amateur tournaments would put him on some of the most storied courses, places like Pine Valley, Seminole, Fishers Island, he was sold.

By 2021, Holderness & Bourne was booming, and he stepped back into competing.

He qualified for the first U.S. Mid-Amateur, reaching the quarterfinals that same year.

“That opened up some doors to me,” he said.

“You get a few invitations from there. And you go, and you see how you do, and started playing better.”

An Ohio Amateur title at Canterbury followed in 2023, with another the next year.

Just two years later, he was at the 2026 U.S. Mid-Am at Sand Valley.

A lot of what he learned at CSU showed up.

“I’d say my grittiness, my ability to have confidence in myself even when things are going wrong,” he said.

“…Even if the ball’s not going exactly where you want it to, I still have the tools in my toolbox to get it done. That’s a lot of what Steve Weir instilled in us players: Every day’s not gonna be your day. But you still need to have the strong foundation that can help you get it done when the dominoes aren’t falling in your direction. You can be gritty for a few holes, and then you can find it again, and keep going.”

After he won the title, Weir texted him a screenshot of the 2009 Ohio Open pairing when the two first met.

What would you think about this guy winning that tournament? Steve joked.

Andrew laughed.

“He would have never had a shot.”