Original plan had to change, but Cardinals’ prospect Masyn Winn is still on a path toward the major leagues

*Note: This is a long-form feature that Rob Rains did on Masyn Winn Nov. 3, 2022 after interviewing him at the Arizona Fall League. For updated article on Masyn Winn being called up to the Cardinals Thurs. Aug. 17, 2023 CLICK HERE.

By Rob Rains

There has always been a plan.

From the time that Masyn Winn was 13 years old, the plan was to make Winn’s dream of playing professional baseball and becoming a major-leaguer a reality.

The plan was the reason Winn’s mom, Tiffany Rawson, had him take “Money Matters” as a freshman in high school, so he wouldn’t one day become a bankrupt professional athlete. It was the reason she told one teacher why Winn wasn’t going to play football in high school – because “he’s got a million-dollar arm.”

It was the reason Andrew Guerrero has known Winn since he was a sophomore in high school in Kingwood, Texas, two years before he officially became Winn’s advisor and agent.

It was the reason why, when Winn’s school guidance counselor told Rawson, “I don’t think you are getting him ready for college,” Winn’s mom agreed with her.

“You are correct,” Rawson told the counselor. “I’m getting him ready to be a professional athlete out of high school … Her and other people thought I was that crazy mom.”

By the time Winn was a junior, the plan seemed to be progressing well. He split time between pitching and playing the infield, going 13-0 with an 0.67 ERA on the mound, striking out 117 hitters in 76 1/3 innings. At the plate he hit .417 with eight homers.

The plan next called for Winn to spend that summer, in 2019, playing for USA Baseball, where he was expected to be the starting shortstop for the national team. A good summer, with success in the showcase events and tournaments, would hopefully set him up for his senior year and a strong chance to become a first-round pick in the 2020 amateur draft.

Winn’s future could not have been any brighter – until the day all of the planning was upended with what Winn says now was “a bad decision.”

“I personally thought my career was over, just being young and naïve,” Winn said.

Kicked off the national team as a result, Winn returned home. “To say he thought his career was over is definitely an understatement,” Rawson said. “He came home and wallowed in it for a while, and I let him, for about six weeks.

“It was tough, it was absolutely heartbreaking. But first of all I have to say I was very proud of the fact that he was honest from the beginning. The kids that he was with were not, and they didn’t get quite as severe a punishment as he did.”

Said Guerrero, “Masyn was honest and owned up to his mistake. He didn’t run away from it. He’s learned from it, and I  think ultimately in the long run it’s made him a better person.”

At the time, naturally, Winn was more concerned with what he had lost, the opportunities that had been taken away from him that he didn’t know if he could get back. The life lessons that would come out of the experience would come later.

“A new plan”

After giving her 18-year-old son what she thought was enough time to be depressed, Rawson told Winn it was time for “a new plan.”

She told Winn, “You’re going to have to work a hell of a lot harder. Now you’re going to have to prove yourself more.

“At first he didn’t want to. The plan he had had was gone. Then he started to have a little success. He found out, ‘I can still run. I can still hit. I still love baseball.’”

With the renewed guidance of his mom, and the help of a close circle of friends, Winn accepted the challenge to not let one teenage mistake derail his years of hopes, dreams and hard work.

“She’s played the mom and dad role my whole life,” Winn said. “She’s had the biggest impact on my life in baseball and everyday life in general. She pushed me as hard as she could in school and whatever sport I was playing at the time. She was always on top of things.”

Rawson knew that if Winn worked hard enough on the field, given another chance, his God-given ability was still there. So too were aspects of his personality that had not been lost, the leadership skills and outgoingness that Winn had displayed all of his life.

The youngest of her five children, Rawson saw early on that Winn “was different” than his older siblings.

“All of my kids were athletes,” Rawson said. “My daughter played basketball in college but she did just exactly what she had to do. My oldest son had the heart and the drive but didn’t have the body. He’s had three knee surgeries and two shoulder surgeries. My second son had awesome athleticism and the body but not the heart or the drive.

“It was pretty clear when Masyn was eight or nine years old that he was different. You could just tell. He was built differently. He was wired differently. You could just kind of tell he might be the one who has it all.”

Rawson remembers taking Winn to a doctor’s appointment on his first birthday. Waiting in the room, the two were playing catch with a small, squishy basketball when the pediatrician walked in and saw them.

“She goes, ‘You know that’s not normal right (for his age)?” Rawson said. “She said, ‘He should not be able to throw and catch like that at 12 months old.’ I said, ‘Yeah, we’ve been doing this for two months.’”

It took a few more years before Rawson began to encourage the development of Winn’s other skills.

“I have challenged all of my children,” she said. “We’re all outgoing. We all talk. We all have great personalities. I tried to make them understand what a gift that is, how difficult it is for shy people. I walk into any room and find the one person who isn’t talking to anybody and pull that person into a conversation. Any new kid that joined any team my kids were on, it was their responsibility to bring them in and make them part of the group.

“I pushed Masyn. Masyn was so popular at 4. He was popular at daycare. He’s bright. He’s funny.  I’ve always made him do things. They used to play a football game with shirts and skins before the season started and kids would only throw the ball to kids they knew. After practice one day I told him, ‘See that little kid over there? Tomorrow, throw him the football please.’

“He threw it to him twice and the other parent was crying. I told Masyn, ‘You will never remember that kid’s name but he will never forget you. Those little things you can do because you’re popular, because everybody follows you or listens to you, can be a huge difference.’ He was really good at it.”

Because of that personal history, Rawson – and Guerrero – believed that when Winn got back on the field his ability would take over. Getting to talk to scouts, and explain what had happened truthfully without making excuses, would be an important aspect of his recovery path as well.

“It was not a representation of who he was or what his character was,” Guerrero said. “I told him to go work his tail off and prove to everybody this is not going to define you.”

The first part of that process was to find a place for Winn to play.

“The best leader I’ve ever been around”

Winn’s former summer team had disbanded. Committed to Stanford at one point, keeping his college options open, Winn had changed his choice to Arkansas. One summer travel team, the Arkansas Sticks, had a roster that included several other future Razorbacks.

The coach of the Sticks, Chase Brewster, met with Winn and his mom. It didn’t take long before Winn joined the team.

It also didn’t take long for Brewster to learn, as others had, what Winn brought to his team above and beyond his ability to hit, run and throw.

“He was the best leader I’ve ever been around,” Brewster said. “Masyn’s motives were always Kobe Bryant-ish. You hear stories and they are hard to believe, but that’s who Masyn was. He was going to win everybody over either by working hard or his character. He left an impression on everybody he was around.

“He was one of the greatest kids I’ve ever been around. I wish I had a hundred of him … He knew what he wanted to do. He was well-educated, he was talented. He loved to play baseball, he loved to compete at the core, and he loved to see other people who were not as talented as him do well.”

The first chance for Winn to show a large group of scouts he had not lost any of his  talents since leaving the USA team came in October 2019, at a Perfect Game tournament in Jupiter, Fla.

“It was a big tournament for me, especially with everything that had happened,” Winn said. “I had something to prove there.”

Brewster still has a video he took on his cell phone one morning of Winn, in full uniform, taking dry swings at 6:50 a.m., hours before the team’s game was scheduled to begin. Winn was determined to make the most of this opportunity.

“He was embarrassed and used that as fuel,” Guerrero said. “I think that’s a good lesson for a lot of kids coming up in this day and age. He went out and put on a show that scouts to this day call the best performance they’ve ever seen.”

On the mound Winn threw a fastball that registered 98 miles per hour on the radar gun. One of his three hits in the game was a home run. All three of his hits had an exit velocity greater than 100 miles per hour.

While that performance was a boost to Winn’s confidence, he soon found out the repercussions of his mistake were going to linger a while longer.

Word about what had happened had reached his high school, and when officials asked for an explanation, Winn again told the truth. He was suspended for the first 12 games of his senior season, an important time for him to try to make an impression on scouts getting a final look at players before the draft.

“They said if I had lied I actually wouldn’t have been suspended,” Winn said, “but I told them what happened and we just kind of went from there.”

“I like to talk a lot”

Winn’s strong junior season and earlier success already had made him well known to Jabari Barnett, then the Cardinals’ area scout in Texas and now their Midwest crosschecker.

“Coming into the spring we knew that Masyn would have to serve a suspension but he would be allowed to play in scrimmages,” Barnett said. “Our plan was to get to more scrimmage and practice looks than we would normally get.

“Masyn is one of those players where you hear about him before you actually meet him, and there was no shortage of opinions. The more we got to know him we realized that some perceptions were harsher than our perceptions of his makeup. He was highly charismatic, had a great sense of humor and confidence in himself on and off the field.”

Barnett remembers one of those pre-season scrimmages in particular in part because it was cold, at least by Texas standards, about 40 degrees.

“It was a 13-inning scrimmage,” Barnett said. “I remember the competition wasn’t great and the game was a bit slow but Masyn was locked in the whole game, all 13 innings. I know because I heard him the whole time. He didn’t stop talking; on the field, on the edge of the dugout, for 13 innings.

“That night stands out because it gives some insight into who he is. In a meaningless scrimmage, in cold conditions, in a non-competitive environment, he provided the energy, found a way to compete and encourage those around him.”

Winn remembers that night, and he’s not surprised that what stood out to Barnett was how much he talked during the scrimmage.

“I’m real energetic,” Winn said. “I like to talk a lot. I’m a real positive guy and I would say I talk more than most people. I like being the vocal leader out there, always keeping everybody on their toes, always trying to be positive when I can. I think it feeds to the other guys. I’ve always loved talking. It’s just natural.”

Winn remained positive during his suspension, using his time to encourage his teammates. What nobody had any way of knowing, however, was the challenge that was about to affect the country and the world.

Winn was able to play one game after his suspension ended before the rest of his team’s season was canceled because of the pandemic. Every team pulled their scouts off the road. There were no games to watch, no chance to evaluate players in the critical final weeks before the draft.

“The biggest challenge was not being able to watch workouts, game, etc.,” Barnett said. “There were months between the last time we saw him in person and the draft.”

What neither Barnett, Winn or anybody else knew at the time, however, was that the shutdown probably worked to the benefit of the Cardinals. Relying on what they knew, aided in part by the evaluation of another scout, Dirk Kinney, who doubles as a coach for the Sticks, the Cardinals were able to draft Winn with their second round pick, the 54th overall selection.

“In my honest opinion, if there had been a normal season, Masyn might not be a Cardinal right now,” Barnett said. “I was concerned if he would get to our second pick. If there was a normal season I think there is no way he gets there. I’m not sure how other teams evaluated him but with a full schedule I assume it would have given more time for teams to buy in.”

As he has learned on other occasions in his life, Winn still believes it was another reminder of a lesson his mom taught him years ago – that everything happens for a reason.

“Personally, I think if I wouldn’t have gotten in trouble I would have gone closer to the first round,” he said. “That’s not something I can really control now. It could have changed everything. I doubt if I would be a Cardinal. All that doesn’t even matter at this point. Now it’s all about playing ball and trying to get to the big leagues.”

“You can’t take your eyes off him”

As Winn sat in the dugout before a recent Fall League game at the Peoria Sports Complex, he preferred to look ahead, not behind. After spending the summer of 2020 at the Cardinals’ alternate site training camp, two good seasons in the minors have put Winn on the doorstep of the major leagues.

“I knew there were for sure going to be some character questions coming in (to pro ball),” Winn said. “I wanted to, and I’m still trying every day, to prove to them that I’m the guy they drafted and the guy they want to lead their team in the future.”

Rawson has seen a change in her son over the last two years.

“He is incredibly focused on the end game,” she said. “It is interesting to talk to what is a 20-year-old child whose goal is to get to the big leagues. Nothing is getting between him and that goal. He knows exactly what he has to do to get to the show. That’s his goal.

“It’s quite fascinating, his singular focus on this. There are so many temptations. There’s so many things that can derail you  … I’m not as worried about him as I used to be. He knows what the goal is and he knows what the boundaries are now.”

Kinney spent a lot of time with Winn during the summer of 2019, including staying in the same house along with some of the other players on the Sticks. The two reconnected this summer.

“We had lunch in Springfield,” Kinney said. “I was able to witness the growth he has made.”

Guerrero remembers a conversation with Winn when his pro career was just getting started.

“He said he was in the clubhouse looking around at grown men,” Guerrero said. “He was like everyone who has the questions of, ‘Do I belong here? Am I good enough to compete with these guys?’ He said, ‘You know what? I thought to myself, they’ve still got to pitch me the ball. It’s still baseball. They’ve got to bring it to me and I can show them what I can do.’ I thought that was the perfect attitude to have.

“Baseball is a game of failure. It’s an individual game within the context of a team sport. There’s a guy on the mound and a guy at the plate. It’s one-on-one. You have to be able to put the outcome of your last at-bat behind you and still say, ‘I’m the man, I’ve got this’ and find a way to succeed.”

Guerrero believes Winn already is doing that – and will continue to do so.

“He’s going to be able to impact a ball club in numerous ways,” Guerrero said, “with his bat, his glove, his speed, with his five-tool approach. He’s someone who if you are on the other team, you have to game plan around him.

“You can’t take your eyes off him when he is on the field because he can impact the game in so many different ways.”

Barnett has paid close attention to Winn’s journey since his high school days.

“I know that whenever Masyn steps on a field that he believes he’s the best player out there,” Barnett said.

That’s been the case this fall, just as it was the last two years. Splitting this season between Peoria and Springfield, Winn hit .283 with 36 doubles, 12 homers, 63 RBIs and 43 stolen bases in 119 games. In his first 16 games in Arizona, he hit .320, drawing 12 walks while striking out only nine times in 50 at-bats.

“Masyn has a ton of energy and plays the game at a really high rate,” said Tyger Pederson, Winn’s hitting coach at Springfield and also with the Salt River Rafters this fall. “He cares. That’s the biggest takeaway for me; when you get a player who really plays hard and cares, that’s what you want.”

The Cardinals drafted Winn as a two-way player, interested in seeing how he would develop as both a hitter and a pitcher. He has played so well at shortstop that the idea of also pitching –   he has thrown only one inning as a professional – has at least for now become an afterthought.

“It’s in my back pocket right now and probably will end up staying there,” Winn said.

When the Fall League ends soon, he is going to go home and rest over the holidays.Then he and fellow top prospect Jordan Walker, now one of Winn’s closest friends, already have plans to arrive in Florida in January to begin preparing for next season.

“Masyn will have other goals,” his mom said. “Getting to the big leagues is the first goal. He’s already planning.”

Follow Rob Rains on Twitter @RobRains

Photos courtesy of Arizona Fall League and MLB and Arkansas Sticks

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For the latest news and features in St. Louis Sports check out STLSportsPage.com. Rob Rains, Editor.