Ryan Dempster

speaker

1,598 appearances 12 recordings 5 series first heard Dec 2025 last heard 19 Jul

Ryan Dempster’s voice in public audio — every appearance, attributed to the second.

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recordings per month · last 12 months

Recordings per month over the last 12 months — 12 in all, peaking in May 2026 with 3.

Appearances

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Rahimi & Grote Show · Ryan Dempster talks Tom Ricketts' high expectations for Cubs · 17 Feb 2026 podcast

Finances changed.

People left.

Other players got traded away.

All kinds of stuff.

And then you start to miss the playoffs, right?

as a player, as a front office, as an organization, as an ownership.

And then you get it again, and you're like, wait, wait, wait, I really love this.

This is fun.

I want to do this all the time.

I want us to win a World Series again.

And that should be the standard, and I'm glad that Tom talked about that because I know how much he wants to win, and he wants to do it year in, year out.

Like, listen, not everybody's going to be the Dodgers and good for them.

Like, they spend the money, and they're setting the standard standards,

getting players and developing a winning culture.

People are like, the big bad Dodgers, the big bad Dodgers.

2012 Major League Baseball was paying their payroll in April.

Yeah, it wasn't that long ago.

It's not like this has been going on for 25 years.

We see ebbs and flows of different teams doing this, where they're kind of the powerhouse for a little bit.

I think it's time that the Cubs got back to being in that conversation.

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