Hardcore baseball fans probably remember the name Jon Singleton. He was at one point the top prospect in the Astros’ system—ahead of even Jose Altuve. But he struggled at the plate in 114 games in 2014 and ’15 and was released in ’18 after being suspended three times for testing positive for marijuana. Singleton is back with the Astros now, though, and played a key role in their thrilling win over the Orioles last night.

Singleton rose to national prominence when he signed a five-year, $10 million contract extension in 2014, the largest ever to that point for a player who had yet to appear in an MLB game. The contract gave him financial security, but it came with downsides as well.

“I had a lot of anxiety and depression,” Singleton told USA Today earlier this year, “and a lot of that had to do with the contract I signed. I became worried about what people were saying about me. I had such expectations of myself, I didn’t know how to deal with the anxiety, or how to deal with the depression at that age.”

When he made his big league debut in June 2014, he didn’t show the same power that he had in the minor leagues. He batted .171 with a .621 OPS in parts of two seasons, then spent the entire ’16 and ’17 seasons in the minors. Before the start of the ’18 season, Singleton, who said in ’14 that he was addicted to marijuana, was suspended 100 games for a third positive drug test and released by the Astros.

Singleton spent 2018 and ’19 out of baseball, focusing instead on working out and bettering himself. He told the Houston Chronicle this week that he started going to therapy with his wife. In late ’19, he thought a comeback was possible. He signed to play in the Mexican league for the ’20 season, but the pandemic threw a wrench in those plans.

However, Singleton mashed in Mexico in 2021 hitting .321 with an 1.196 OPS and 15 homers in 46 games. That earned him a minor league deal with the Brewers for the following season, where he hit .219 with an .809 OPS and 24 homers in 134 games at Triple A. In June, the Brewers called him up for his first MLB appearance in eight years. When he was designated for assignment after 11 games, he elected free agency instead of going back to Milwaukee’s Triple A affiliate.

That set up a reunion with the Astros, who signed him to a minor league deal and sent him to Triple A Sugar Land. The combination of Singleton’s performance in Sugar Land (.333 batting average, 1.138 OPS and 12 homers, including a 466-foot bomb) and the offensive struggles of first baseman José Abreu led Houston to call Singleton up yesterday.

In the ninth inning of last night’s game against the Astros, 2,867 days after his last appearance with the Astros, Singleton was called on as a pinch hitter. He led off the inning, facing Baltimore’s unhittable closer, Félix Bautista, with Houston trailing 6–3.

Singleton started an Astros rally by working a walk on a full count. Two Houston singles later, the bases were loaded for Kyle Tucker, who hit a grand slam to give the Astros a 7–6 lead. Ryan Pressly closed it out with a one-two-three bottom of the ninth to give Houston a big win in the first game of the series between two of the top teams in the American League.

At this point in his career, Singleton isn’t going to develop into the All-Star many people thought he would be a decade ago. But he’s the only lefty hitter on the Astros’ bench, which gives him an opportunity to take some significant at bats down the stretch for a team with World Series aspirations. Even if he gets sent back down eventually, playing a key role in a dramatic victory for the team that gave up on him eight years ago is a remarkable full-circle moment that he’ll cherish forever.

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Junfu Han/Detroit Free Press / USA TODAY NETWORK

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The top five...

… things I saw last night:

5. The “Free Kevin Brown” chant by Orioles fans in response to the team’s controversial decision to suspend the broadcaster.

4. The chaotic penalty shootout between Nashville SC and Club América in the Leagues Cup. América appeared to have won, but a replay review determined that the goalie was off his line when he made the save, allowing Nashville another chance.

3. Dodgers outfielder David Peralta’s home run robbery.

2. Minnesota United’s beautiful second goal against Toluca.

1. Julio Rodríguez’s home run robbery fake-out. He acted like the ball went over the fence, only to reveal several seconds later that he’d actually caught it.

SIQ

On this day in 1976, Cal Hubbard became the first—and thus far only—person inducted into which two Halls of Fame?

Baseball and Pro Football
Hockey and Basketball
Baseball and Rock and Roll
Basketball and College Football

Yesterday’s SIQ: True or false: Two-time WNBA MVP A’ja Wilson, who turned 27 on Tuesday, was named after a Steely Dan song.

Answer: True. The song title (and album of the same name) doesn’t have the apostrophe, but it is the inspiration for Wilson’s name.

Wilson’s father, Roscoe, explained in a 2018 interview with Women’s Hoops World.

“I went to a Steely Dan concert in either Sweden or France,” he said. “I always liked Steely Dan, and at the concert they had this album Aja, in 1977. I just like the song, ‘Aja.’ And the name, simple—you spell it backwards, forwards, same thing. I said, back then, if I ever have a daughter, I’m going to name her Aja. And I kept my word; when A’ja was born I said, we’re going to name A’ja, A’ja.”

A’ja’s middle name is Riyadh, after the city in Saudi Arabia, because she has an aunt (her mother Eva’s sister) who was stationed there during the Gulf War. Roscoe explained in that same interview that he was in an airport with his wife while she was pregnant with A’ja, and there was a flight to Riyadh leaving from an adjacent gate. Roscoe said he “took it as an epiphany” and decided to give A’ja the middle name Riyadh.

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