Singleton travels arduous path for second chance at The Show

Former top prospect 'very confident' entering Brewers camp

March 7th, 2022

PHOENIX -- When Jon Singleton took the field with Brewers Minor Leaguers on Sunday, it had been four years since he stepped foot in a Spring Training camp. And it had been eight years since the spring he looked a reporter from the Associated Press in the eye and said, “At this point, it's pretty evident to me that I'm a drug addict.”

Then, Singleton was one of the best prospects in baseball. So good that the Astros handed him a five-year, $10 million contract before he played a single big league game.

Now, he is 30 years old with a checkered Major League record, but also the spark of a comeback. He signed a Minor League contract with Milwaukee in December and is back in affiliated ball with prospects nearly half his age, determined to make the most of what Singleton calls “a second chance, a fresh start, a reset.”

“It started with what I guess you can call a candlelight,” he said, “and it turned into a bonfire at some point.”


“I just ran into him for the first time,” said Brewers special assistant Quinton McCracken, who was once Singleton’s farm director in Houston. “It's easy to run into him. You can't miss him.”

That was always the case. Singleton is a mountainous first baseman who stands 6-foot-2 and was listed at 230 pounds in the Astros' media guide when he was perched atop prospect charts. Houston had acquired Singleton from the Phillies in the Hunter Pence trade in 2011, and he went on to become the organization’s top prospect and a Top 50 prospect in baseball.

At 22 years old in June 2014, having already raked at Triple-A, Singleton became the first player to sign a multiyear, multimillion-dollar extension before playing a Major League game. He made his debut the following night and homered in a win over the Angels in Houston. Options and bonuses in his contract could push the total value to $35 million over eight years. It had the potential to be a bargain.

But it did not turn out to be a bargain. Singleton hit 13 home runs in 95 games for the Astros that year but batted .168 and struck out at a 37 percent clip. Called up again in 2015, he hit .191 with one home run in 19 games and was demoted back to the Minor Leagues, where he spent the rest of that season and all of ’16 and ’17.

Meanwhile, Singleton was running into trouble off the field. Before signing his big contract, he had twice run afoul of Minor League Baseball’s drug testing policy for marijuana use and had served a 50-game suspension in 2013. He told the AP he had gone to an inpatient treatment facility for addiction. In January 2018, MLB announced that Singleton failed another drug test, and this time the league slapped him with a 100-game ban. The Astros released Singleton that May.

“I really wasn't thinking too deeply about any choice, any situation I was in,” Singleton said. “I was doing what was right in front of me.”

Today, he has a different perspective.

“I had to get away from baseball in order for things to slow down and for me to personally hit that reset button,” Singleton said. “I made some changes in my personal life with my friends and family and stuff like that, and ultimately, that led me to better habits.

“It gave me new opportunities as well, you know? I opened a gym last year. That was a big starter for me to come into this organization. I’ve been working so hard. And also it shows these little kids that it doesn't matter what you did -- if you put forth the work, you can make things happen.”

Singleton said the gym, which opened in December 2020 in Buena Park, Calif., has helped him get back into shape after he ballooned beyond 300 pounds. It also has served to keep him honest and busy. Its members, Singleton said, are mostly young ballplayers, but also includes a mix of college players and pros. He is open with them about the ups and downs of his baseball career.

“Definitely. They know all about it,” Singleton said. “And they see that I'm there and the amount of work that I put in on a daily basis.”

Over the course of the past several years, Singleton says he dropped 75 pounds and felt ready to try a comeback. So Singleton signed last summer with Diablos Rojos del México, a Mexico City-based club that included fellow former Major Leaguers Yangervis Solarte, Jorge Cantu and Gorkys Hernández. The league is generally hitter-friendly, but features legitimate talent; Singleton immediately became one of its best hitters. He posted a .321/.503/.693 slash line with 15 home runs in 46 games.

Milwaukee took note. Brewers president of baseball operations David Stearns was Houston’s assistant GM when Singleton signed his contract, and McCracken, who joined Milwaukee’s organization in 2021, was Singleton’s farm director with the Astros. The two have remained close via a group text thread on which McCracken shares Christian scripture and motivational messages.

“He's definitely been a big part of my life the last three, four years,” Singleton said. “He's great about checking on me about my life. I really appreciate that.”

Said McCracken: “Things aren't always linear. Things went kind of sideways for Jon. He addressed it, he's been open with his struggles. As teachers and educators in this game, I know we've always stressed the fact that you've got to take care of the man first, and then player will emerge from there. He knows that.”

Singleton was asked whether it’s been difficult staying on the right path.

“I mean, once you get to a certain point, it just becomes routine,” he said. “But getting to that point is difficult. You definitely have to remind yourself why you're doing it.”

He’s doing it to get back to the big leagues.

“Based on the work we’ve done, we believe he deserves a chance here,” Stearns said late last year, after the deal was finalized. “Certainly, [the suspensions] are a part of his story for as long as he’s in the game, and we’re cognizant of that. He’s cognizant of that. But we believe he deserves a chance and we’re going to give it.”

Singleton, who is eligible for the start of the 2022 season (whether that’s in the Minors or the Majors), is one of a number of former top prospects getting a shot with the Brewers. Coincidentally, also among them is Tyler White, who happened to be called up by the Astros the last time Singleton was sent down. Milwaukee also has former Rockies outfielder and National League All-Star David Dahl back on a Minor League deal after acquiring him last year, plus former Rays Top 10 prospect Garrett Whitley.

“These are guys who were top talents,” McCracken said. “They can come in and maybe, you know, surprise some people. Open some doors. Kick some doors in.”

That’s the goal for Singleton.

“I'm very confident,” he said. “You know, there are days -- I wouldn't say I'm worried, but you still kind of have a little doubt, you know? If you don't have a little doubt, then why would you work so hard? That little doubt allows me to stay on the right path. I still have more work to do to get to where I want to get to.”