Ryan Dempster is one of four pitchers to make 300 starts and save over 80 games in the big leagues since 1969.

So, if anyone is qualified to discuss the evolution of a pitcher, Dempster is that guy.

The former Cubs pitcher sat down with Marquee Sports Network’s player development analyst Lance Brozdowski on the Cubs Weekly Podcast to talk about pitch mixes, the evolution of pitching and how pitchers hone their grips in different ways.

Dempster, a 16-year MLB veteran, broke down how a starting pitcher navigates through an opposing lineup and why situational pitching isn’t always just going to one’s best pitch.

“I think sometimes we get so caught up in that data saying, ‘This shape right here will work.’ Yes, it will. But is that the right time to do it?” Dempster said. “It’s like sitting there and saying, ‘An uppercut will knock this guy out.’ Well if you go out in the first round, and all you’re doing is throwing uppercuts … you’re not going to knock the guy out.”

It’s a theme that has come with the modern-day game. Numbers and analytics rule the diamond, but Dempster emphasized that only gets you so far — a pitcher needs to know himself and the situation to execute successfully.

For a fan, pitch grips may seem otherworldly. How does a major league pitcher have the ability to put so much spin, change velocity or add a new pitch in the span of an offseason? Or even in-season?

For Dempster, as it is for many pitchers throughout the league, it took a lot of experimentation to find what works and when to use it.

“I could have written a book on failed changeups,” Dempster said.

Dempster discussed how he and other pitchers used to ask the best in the game about their pitches. Dempster’s splitter — a pitch he didn’t use consistently until later in his career — was inspired by Cubs legend Fergie Jenkins and his own changeup grip.

A similar discussion occurred between Pirates star pitcher Paul Skenes and Cubs ace Shota Imanaga. Famously, in the 2024 season, Skenes and Imanaga discussed Skenes’ fastball grip. The next time Imanaga faced the Pirates, he threw seven no-hit innings to propel the Cubs to a combined no-hitter.

Dempster made clear: It’s not a direct point A to point B process, and another pitcher’s grip doesn’t automatically translate over.

“What might work for me might not work for you,” Dempster shared, “Always continue to tinker with pitches in your hand.”

New pitches and grips pop up seemingly out of the blue – and although pitching and the game of baseball seems overly data-driven, Dempster explains that there are still the methods of old, simple experimentation.

For his full breakdown of his pitch mix, grips, and modern pitching, be sure to check out the Cubs Weekly Podcast.