OSAGE COUNTY — On Father’s Day 2025, Loose Creek native and Fatima High School graduate Will Robertson was living every baseball player’s dream. He made his Major League debut with the Blue Jays, capping a journey that carried him from Osage County to Creighton University, and ultimately to baseball’s highest level since being drafted by Toronto in 2018.

Twelve months later, Robertson’s career has taken several unexpected turns, but the 27-year-old outfielder remains healthy, optimistic, and prepared for whatever opportunity comes next. “I’m kind of a free agent right now, actually,” Robertson said. “I’m in a little more limbo. A year from making my debut, and now kind of where we are, it’s been kind of a roller coaster.”

After the 2025 season, the White Sox designated Robertson for assignment as the club looked to create roster flexibility entering the offseason.

That move, however, did not leave him without options. The Pittsburgh Pirates claimed Robertson, but his stay there lasted only about six weeks before another roster move changed his circumstances.

“I thought I was going to stick with them,” Robertson said. “I had some good connections with them, knew some of the players really well, and had some good conversations with their coaching staff. It came down to they made a trade for two outfielders, and it kind of crunched the numbers again. I was kind of the odd man out.”

The Baltimore Orioles then claimed Robertson, giving him another opportunity and a different spring training experience. “It was my first spring training that I wasn’t with the Blue Jays, so it was a little different,” he said. “But kind of bouncing around the last year has kind of been normal. It wasn’t too bad.”

Although he did not receive many game opportunities with Baltimore during spring training, Robertson appreciated working alongside the Orioles’ Major League roster while surrounded by family support.

“Spring training was good,” he said. “I had my family. Morgan and Jonny were down there with me, and Mom and Dad came and visited quite a bit. So that was good. I didn’t get a ton of opportunities, but I was able to be there with the big league team, meet some of the guys, and work out with a lot of them.”

Robertson opened the season at Triple-A Norfolk before another setback interrupted his progress.

About two series into the season, he dove headfirst into first base, breaking his hand while also rupturing a ligament in his thumb. “I had to get surgery on both of them,” Robertson said.

The surgery sent him to Arizona before allowing him to return home briefly while doctors restricted nearly all physical activity.

“They wouldn’t let me sweat or do anything because I had a pin in my hand,” he said. “So they let me come home, thankfully, which was nice to be home in May for the first time since COVID.”

Robertson then returned to Florida for approximately eight weeks of rehabilitation, which he described as tedious, particularly because so much of baseball depends upon the thumb. “The rehab process with a thumb is kind of frustrating,” he said. “You’re doing these little exercises and holding one-pound weights and bands, trying to get your thumb to work again. You kind of take it for granted until you don’t have it.”

While swinging the bat returned more quickly than expected, throwing proved more difficult.

“Throwing, just getting the feel because it was my left hand, just having that grip with the thumb and letting it go, that was actually more of a challenge than I thought,” he said. “Hitting-wise, I felt good.”

After being medically cleared, Robertson expected to return to Triple-A.

Instead, another roster crunch altered his plans. “I was ready to come back,” he said. “I was ready to go, and the Orioles said that at their Triple-A level they just had too many guys. They signed some guys for injury and stuff like that, and so they actually released me. So now I’m able to see if any other teams want me.”

Despite the uncertainty, Robertson said he believes he is fully healthy and prepared if another organization calls. “If a team wants to pick me up, I’m ready to roll,” he said. “I’ve got Dad feeding me machine balls in the cage and throwing down at the ballpark, trying to stay as ready as possible.”

His daily routine closely mirrors his offseason training schedule.

Each morning begins with strength training in the family weight room before evenings are spent hitting and throwing with his father, Jon Robertson.

“Other than getting to see live pitching, which is really tough to emulate, I’m pretty much trying to do everything the same,” he said.

While waiting for the next opportunity, Robertson acknowledges there is uncertainty surrounding both his own future and the professional game.

“I wouldn’t say I’m nervous,” he said. “There’s just uncertainty with the sport right now and in my situation, yeah, a lot of uncertainty.”

Still, Robertson said his perspective remains grounded in faith. “I think I’ve echoed this before that it’s God’s plan,” he said. “If no team wants to pick me up and I don’t play baseball professionally again, I’m okay with that, too.”

Like many professional athletes, Robertson admits he has thought about life after baseball but has intentionally resisted making concrete plans.

“As a husband and a father, you’re always trying to plan the next step,” he said. “I haven’t really let myself go there quite yet with what I would like to do post-baseball.”

One thing he does know is that baseball has shaped nearly every aspect of his adult life. “I always joke with Morgan that I feel like I have a Ph.D. in baseball,” he said. “I feel like the last 12 years I’ve been playing this game pretty much every day other than the offseason.”

Whether that experience eventually leads into coaching or another baseball-related career remains to be seen. “I think it would be cool to do something with baseball,” he said. “I don’t know what opportunities would line up with Morgan and I’s lifestyle.”

If baseball eventually comes to an end, Robertson hopes his future remains close to home. “I would love to stay around Osage County if I could,” he said.

That commitment to family is already evident. In 2020, Will and his wife, Morgan, purchased the home just below that of his grandparents, Glenn and Kathy Robertson, allowing them to remain close while raising their daughter, Jonnie.

Morgan also works remotely about 20 hours each week in a flexible position  for Missouri Medicaid’s prior-authorization department, allowing the family to travel together during baseball season.

Robertson joked that if professional baseball doesn’t work out, he may already have a fallback. “I joked around with Robbo,” he said with a laugh, of his uncle, Ryan Robertson. “I told him if you need any help on the turkey farm, you’ve got a hired hand.”

Then, still smiling, he added another possibility. “I guess that’s the good thing about having the family farm there,” he said. “That’s always a nice backup. Ryan and Grandpa might not want me. They might think I’m a waste of space and can’t do anything anymore.”

For now, however, Robertson isn’t ready to think of baseball in the past tense. His agent has advised him that the period immediately following the Major League Baseball draft and the All-Star break could create new opportunities as organizations reassess their rosters.

Until then, Robertson plans to keep training, keep waiting, and keep believing another opportunity will come. “I’m hopeful here in the next couple of weeks that a team picks me up,” he said.