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Base Paths to Drag Strips, a Tale of Risk & Reward


Bob Wilber
Bob Wilber, former pro baseball player and author of "How Far?"

The World Series is now over and for baseball fans, we’re in that never-never land where all we can hope for is a bit of news from our favorite team while we’re sitting out the long offseason until spring training begins in February.

But I’ve got an idea about something that can help you pass the time. Pick up a new book by today’s Lean to the Left podcast guest, Bob Wilber. It’s called “How Far,” and it explores the incredible friendship between a baseball player from Southern California and a hockey play from Minnesota.


It's an inspiring story for sports fans, yes, but really for anyone who wants to be motivated to achieve their goals despite the curve balls and sinkers that inevitably are thrown in their path.


As the son of a major league baseball player and a former pro baseball player himself, Bob

Bob Wilber

Wilber has lived the athlete’s life. How Far? weaves the compelling story of two disparate athletes who meet and form an unlikely bond.


His creative use of first-person writing, having his fictional protagonists appear to write the book themselves in their distinct voices, immerses readers in every thought and word of the two characters.

Brooks Bennett is a gifted baseball player (and the son of artist hippies) from Southern California, and Eric Olson is an undersized hockey player from Roseau, Minnesota — where hockey is king. The two men come from vastly different worlds and couldn’t be more dissimilar. And in one spontaneous moment, their paths cross, and their lives change forever.

It's a fun and interesting story, especially if you enjoy sports and an inside look at what it's like trying to pursue a Major League Baseball career, and then adapting to life after baseball.


Here are some questions we asked Wilber:


Q. You’re the son of a Major Leaguer, your mom was a radio personality and then a PR person. You played college and professional baseball and then went into high level sports marketing while also running three different professional indoor soccer franchises as an executive.


Then, you launched a 22-year career as a manager and PR rep for a couple of highly successful and popular Nitro Funny Car teams on the National Hot Rod Association tour.


After all that, you walked away to become an author! You’ve just published your second book and it sounds like it’s getting rave reviews. Tell us about how you adapted so much throughout your career…


Q. I get that you had baseball in your DNA thanks to your dad, and after your professional playing days were over you even were a regional scouting supervisor for the Toronto Blue Jays. But how in the world did you make the shift to NHRA drag racing?


Q. After all of that, why walk away to write books? What in your mind told you to go for it and start writing books? That’s a bold leap!


Q. So your autobiography, “Bats, Balls & Burnouts" was a hit, and you decided to write another book. Tell us how you settled on the premise and style for “How Far?”


Q. How much of "How Far?" is totally real and how much is fiction?


Q. And that begs the question: If your two main characters in “How Far?" are fictional, who are they based on?


Q. How did you even pick those guys, those sports, and their personalities?


Q. Is it a sports book? Would it appeal anyone other than sports fans?


Q. Let’s talk some baseball. Are you still connected to the game in any way?


Q. What did you think of the World Series, the upstart Phillies against the incredible Houston Astros and Dusty Baker?


Q. What are your thoughts about the influence of money on the game today? For example, the LA Angels’ ownership say they won’t trade Shohei Ohtani, the incredible two-way player who’s contract expires at the end of the 2023 season, for which he will earn $30 million guaranteed. But what will he command going forward?


Q. And how about the Yankees’ Aaron Judge, who shattered the American League home run record in 2022 and is now ready to enter free agency?


Q. Do you think these kinds of mega contracts are good for baseball?


Q. What’s next for you?


Listen to the podcast:






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