On this episode of Deals and Deadlines, Matt and Hadley sit down with Bobby Heck, Assistant to the President of the Tampa Bay Rays, to dive into the fast-paced, high-stakes world of MLB free agency. Bobby shares insider perspectives on what it takes to navigate one of baseball's most chaotic times of year.

The trio also tackles the buzz surrounding Juan Soto’s blockbuster deal—breaking it down from every angle. What does it mean for the Padres, the league, and the future of mega contracts in baseball? Expect sharp insights, behind-the-scenes anecdotes, and a few laughs as Matt and Hadley ask the questions every baseball fan is dying to know.

Tune in for an episode packed with exclusive baseball intel and a front-row seat to the big leagues! ⚾

On this episode of Deals and Deadlines, Matt and Hadley sit down with Bobby Heck, Assistant to the President of the Tampa Bay Rays, to dive into the fast-paced, high-stakes world of MLB free agency. Bobby shares insider perspectives on what it takes to navigate one of baseball's most chaotic times of year.
The trio also tackles the buzz surrounding Juan Soto&rsquo;s blockbuster deal&mdash;breaking it down from every angle. What does it mean for the Padres, the league, and the future of mega contracts in baseball? Expect sharp insights, behind-the-scenes anecdotes, and a few laughs as Matt and Hadley ask the questions every baseball fan is dying to know.
Tune in for an episode packed with exclusive baseball intel and a front-row seat to the big leagues! ⚾

"Chuck and Chernoff" with Chuck Oliver and Matt Chernoff airs weekdays from 2-6pm on 680 The Fan, WCNN-AM and the 680 The Fan App. 

"Chuck and Chernoff" with Chuck Oliver and Matt Chernoff airs weekdays from 2-6pm on 680 The Fan, WCNN-AM and the 680 The Fan App.

Chuck and Chernoff

"Chuck and Chernoff" with Chuck Oliver and Matt Chernoff airs weekdays from 3pm to 7pm on 680 The Fan, WCNN-AM.