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Grace Woolwine was a walk-off hero Monday for Shepard.

It wasn’t her first time. That happened last year, when her hit ended a 10-0 win over Argo.

This one, though, was much more dramatic. It came with two outs in the bottom of the seventh inning and lifted the Astros to 6-5 win over Mother McAuley.

“I just thought about what my job was and what I wanted to get done,” Woolwine said. “Honestly, I thought I was going to be out. But then the ball took a hop. I knew then the game was going to be over. It was pretty exciting.”

Woolwine, a junior who plays three sports, is building quite a portfolio as one of Shepard’s toughest and most durable female athletes.

In the fall, she’s the starting quarterback for the flag football team. In the winter, she’s a starting guard in basketball. This spring, she’s the quarterback behind the plate in softball.

Shepard's softball catcher Grace Woolwine during a practice in Palos Heights on Tuesday, March. 31, 2026 (James C. Svehla / for Daily Southtown)
Shepard's Grace Woolwine frames a pitch during indoor batting practice in Palos Heights on Tuesday, March 31, 2026. (James C. Svehla / Daily Southtown)

Shepard coach Bridget McDermott defined Woolwine in two words.

“Major competitor,” McDermott said. “You can tell when she’s angry and wants to win. I think you can love to win but you also have to hate to lose. And I think Grace hates to lose.”

Woolwine wasn’t angry during Tuesday’s indoor batting practice at Shepard. There were a lot of laughs. In fact, talking about softball made her … kind of melancholy.

Of her three sports, it’s clearly No. 1.

Shepard's softball catcher Grace Woolwine at bat during a practice in Palos Heights on Tuesday, March. 31, 2026 (James C. Svehla / for Daily Southtown)
Shepard's Grace Woolwine connects on a pitch during indoor batting practice in Palos Heights on Tuesday, March 31, 2026. (James C. Svehla / Daily Southtown)

“Playing softball means a lot to me,” Woolwine said. “I’ve been playing it my whole life. And I’ve been growing so much more the past few years. I like playing softball with all of my friends. When I’m doing it, I just forget everything else.

“When I’m catching, honestly, it’s exciting. You get to watch how the other teams run. You can try to throw them out. And you’re kind of like the hype person. You can go out there and tell people what they need to do and bring them up when they’re down. You kind of control the game.”

She has been at the controls for senior pitcher Anamarie Solorio since their days in grammar school.

“It so easy to work with Grace,” Solorio said. “She knows how I pitch and I know how she catches. She knows when I need a breather or am struggling in a game. She’ll call time and come out to talk with me.”

Shepard's softball catcher Grace Woolwine puts on her gear during a practice in Palos Heights on Tuesday, March. 31, 2026 (James C. Svehla / for Daily Southtown)
Shepard's Grace Woolwine puts on her catcher's equipment before indoor batting practice in Palos Heights on Tuesday, March 31, 2026. (James C. Svehla / Daily Southtown)

If anyone isn’t surprised that Woolwine also excels in football, it’s junior utility player Izzie Belsky.

“We’ve been friends since preschool,” Belsky said. “I remember when we’d play games in her front yard. We’d always toss around a football, and play with her brother Luke.

“When we heard about flag football starting at Shepard, she asked if I wanted to do it. I was already playing volleyball in the fall, so I really couldn’t. But I’m starting to go back and forth about actually playing football with her next year.”

Woolwine was a force for the Astros in flag football. She threw for 17 touchdowns and rushed for five more. At middle linebacker, she came up with six interceptions, including a pick-six.

Shepard's softball catcher Grace Woolwine during a practice in Palos Heights on Tuesday, March. 31, 2026 (James C. Svehla / for Daily Southtown)
Shepard catcher Grace Woolwine pulls in a pitching during indoor batting practice in Palos Heights on Tuesday, March 31, 2026. (James C. Svehla / Daily Southtown)

Not bad for a kid who wasn’t exactly a football expert growing up.

“I didn’t really know anything about football,” Woolwine said. “When they announced they were going to have it here, I was excited. I wasn’t going to be a quarterback at all, but once I figured out how to throw it, I knew that’s what I was going to do.

“Now, I know pretty much everything about the game.”

There’s one thing Shepard’s toughest kid would like to change.

“Yeah, sometimes I wish we had contact,” Woolwine said, laughing.

Tony Baranek is a freelance reporter for the Daily Southtown.