How Iowa Cubs pitcher Caleb Kilian became the Chicago Cubs' most prized pitching prospect

Caleb Kilian chowed down on enchiladas at a popular Arizona restaurant called Dick’s Hideaway during a lunch with his agent Bobby Witt Sr. last fall when the topic of the next season came up.

Witt Sr., who had come to town to watch Kilian throw in the prestigious Arizona Fall League, made a somewhat surprising prediction for his client.

“I said, ‘There’s a pretty good chance you’re going to be in the big leagues in 2022,’” Witt Sr. recalled.

Kilian was still a relatively new member of the Chicago Cubs organization after getting traded by the San Francisco Giants as part of a deal for Kris Bryant. The right-hander, who had yet to pitch above Double-A yet, stopped eating for a brief second and looked up at Witt Sr., a former big-league pitcher himself, in amazement.

“He goes, ‘You really think so,’” Witt Sr. said.

It may have seemed hard to believe for Kilian back then since Kilian hadn't even pitched past Double-A at the time.

But not anymore.

The 24-year-old, ranked the top-pitching prospect in the organization by MLB Pipeline, is inching closer to the big leagues. After a dominant start to the season in Triple-A with the Iowa Cubs, Kilian could be on the verge of his Major League debut this year, just as Witt Sr. predicted.

“It makes me just want to put it all out there, work as hard as I can and give it all I got,” Kilian said. “Because it’s getting close.”

But it has taken time for Kilian to not only get his shot but also develop into the Minor League Baseball star he is today.

Caleb Kilian flies under the radar

Witt Sr. saw pro potential in Kilian right away.

Kilian, who pitched at Flower Mound High School in Texas, was overshadowed early on by other arms on the staff. It included Sean Wymer, a fourth-round pick by the Toronto Blue Jays, and Kyle Johnston, a sixth-round selection by the Washington Nationals, and B.J. Myers, a 35th-round pick by the Tampa Bay Rays. Parker Scott, who went on to pitch at Oklahoma State, and Seth Jordan, who played at West Virginia, were also on the staff at one point.

Then there was Kilian, who pitched sparingly as a sophomore but dominated in intrasquad games.

"We knew how good Caleb was," Flower Mound baseball coach Danny Wallace said.

So did Witt Sr., who discovered Kilian in the summer following his sophomore season. Witt Sr., who pitched 16 seasons in the big leagues, had transitioned into an agent and was living in Texas when he heard about Kilian. He watched one of Kilian's outings and was instantly impressed. Kilian did haven't the velocity of many flame throwing high school stars who garner most of the attention of colleges and scouts. But he did have command of the strike zone with his fastball, curveball and changeup.

Witt Sr. was impressed with Kilian's arm action and figured there was even more there when the pitcher got older and added more weight.

PREVIOUSLY: Caleb Kilian wants to be known as more than a guy from the Kris Bryant trade 

"You're sitting there trying to project and think about what he's going to look like after he puts on 20, 25 pounds and really starts to add some strength and get his man strength, where he can be," Witt Sr. said.

While there was still plenty of potential in Kilian, that's just what it was early on — potential. Kilian said big-league scouts visited him in high school but he went undrafted. Just one college offered him a scholarship: Texas Tech. Kilian, who committed the summer before his junior season of high school, believes other colleges would have recruited him had he not made his decision so early.

But there's no denying the potential that Kilian possessed. He showed some of it in high school and in college when he was a star at Texas Tech. Kilian went 23-6 with a 3.61 ERA and 187 strikeouts over 206.2 innings in his college career. But, even then, he had barely tapped into that potential.

Kilian, who relied heavily on simple stuff, also had trouble difficulties putting on weight. He arrived at Texas Tech at 175 pounds and tacked on 10 pounds over the course of three seasons.

"He was getting a little bit frustrated but he just kept after it," Witt Sr. said.

The Baltimore Orioles selected him in the 20th round of the 2018 draft but couldn't sign him. A year later, the San Francisco Giants took him in the eighth round and signed him for $400,000 more than double the allotted amount for the pick.

That's when his career really took off.

Kilian's career takes off

Kilian's career took off when he joined the Giants' organization.

The Giants helped him with his pitch selection and his mechanics. In college, Kilian threw an arm-side sinker that got a lot of groundballs and a four-seam fastball up in the zone and a curveball. He also occasionally threw a changeup. The Giants gave him a cutter and introduced a glove-side sinker so he was able to command both sides of the plate. The cutter helped his sinker and his four-seam fastball.

"It helped a lot," Kilian said.

The results were electric. Kilian didn't give up an earned run in 16 innings in Rookie Ball and short-season. The 2020 Minor League season was canceled due to the COVID-19 pandemic. But during the off-season that year, Kilian tacked on 10 pounds to his frame by eating Braum's milkshakes every night. It helped him during the 2021 season when he went 3-2 with a 2.43 ERA and 64 strikeouts in 63 innings with San Francisco's Double-A affiliate.

His stuff had gotten so good that Kilian became a sought-after player at the trade deadline. Cubs general manager Carter Hawkins, who was working with the Cleveland Indians at the time, said he wanted Kilian. Instead, it was the Cubs that landed Kilian, along with outfielder Alexander Canario, in the deal for Bryant, a World Series hero in Chicago.

The deal worked out well for the Cubs who got a young bat in Canario and Kilian, a guy they thought could unlock even more potential. So, shortly after picking him up, they started tinkering with some of his pitches. The Cubs changed his curveball and changeup grips. Witt Sr., also provided some important advice and urged Kilian to finish through his changeup.

The moves led to massive success as well. Kilian, whose stock had been taking off, watched it soar in the prestigious AFL. Th league, which includes baseball's biggest prospects, was a stage Kilian shined on. He tossed six perfect innings in the championship game and led his team to a title.

During the successful summer, Witt Sr., could see that Kilian, despite never having reached Triple-A, was on the fastback to the big leagues. He explained to Kilian if he kept pitching well and kept developing like he hoped, he could make it to the majors as early as 2022.

"It's reassuring whenever you have an agent, especially Bobby Witt, whose played a lot of years in the bigs, tell you that," Kilian said.

Witt Sr., may have been right.

Kilian knocking on the door of the majors

After the performance in the AFL, expectations took off for Kilian. He entered the season as the top pitching prospect in the system and fourth-overall in the organization by MLB Pipeline. But Kilian, mostly known as one of the players acquired in the Bryant deal, wanted to carve out his own legacy though.

He's been successful in doing that so far. Kilian began the season in Triple-A for the first time in his career and has had little trouble adjustment.  During his first eight starts with Iowa, Kilian went 2-0 with a 2.06 ERA. Kilian also tallied 41 strikeouts in 39.1 innings, clearly passing his first tests at Triple-A.

“The most impressive thing about Caleb is, even on days when he hasn't had his best stuff or his best command, he's always competed well and limited the damage and I think that's part of the learning process as a pitcher," said Jared Banner, Chicago's vice president of player development.

PREVIOUSLY: Caleb Kilian to start 2022 season in Triple-A with Iowa Cubs

Just like Witt Sr. projected, Kilian grew into a dominating pitcher. Now that he has the strength and size to go along with his command, his stuff is even better. Kilian is throwing in the high 90s and using his changeup, which is getting outs.

And he's now on the verge of a potential Major League callup. Even Banner admitted Kilian is  "not far away."

But Kilian, who enjoys hiking and fishing when he isn't at the park, hasn't let the talk of a possible promotion overwhelm him. There are still things he can improve on. Kilian said holding baserunners is one of them and becoming more efficient in games, after the Cubs took their time with Kilian early in the season, is another.

But's little things at this point after all the massive moves that Kilian has made over the years to put himself in this position. Wallace said there's one other area that most people don't talk about that Kilian has improved at as well.

"I just think that his confidence and from what I've seen is just that, 'Yes, I am this good and I can get this done,'" Wallace said.

The Cubs may soon find out if he has what it takes to get it done at the big-league level. But Witt Sr. has no doubts.

"I think he's going to have a lot of success," Witt Sr., said. "I just think with the stuff that he has and the mentality he has, to me, it's a winning combination.

Tommy Birch, the Register's sports enterprise and features reporter, has been working at the newspaper since 2008. He's the 2018 and 2020 Iowa Sportswriter of the Year. Reach him at tbirch@dmreg.com or 515-284-8468. Follow him on Twitter @TommyBirch.

This article originally appeared on Des Moines Register: Iowa Cubs' Caleb Kilian is Chicago Cubs' top pitching prospect