The Stretch

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On today's episode of The Stretch we are joined by ESPN 1000's David Kaplan. We get into how we had gotten started in Chicago media with no prior experience, some of his best stories on being in media during the 90's, how to fix some of the struggling Chicago teams and more.

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Variety talk show encompassing national stories in pop culture, sports, & the internet hosted by Eddie, Chief & White Sox Dave. Harnessing the dynamic of the Barstool Chicago Radio hour, three longtime coworkers and Chicago locals offer their comedic perspective on news for the common man.

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David Kaplan On Ruining Potential Scottie Pippen Trade & Best Media Stories From 90's

On today's episode of The Stretch we recap the Seahawks dominant superbowl win over the New England Patriots. We get into the comparisons of Caleb Williams and Drake Maye and shut them down as we are happy with our guy. We then get into the Bulls finally start their re-build and make a multitude of trades. We then get into Big Cat not being over White Sox Dave's terrible clock management mistake in Barstool After Dark's Flag Football Tournament.

Putting Caleb Williams Comparisons to Rest, The Bulls (Finally) Begin The Re-Build, & White Sox Dave's Unforgettable Mistake

On today's episode of The Stretch, we get into how Chicago Bears staff members Ian Cunningham and Declan Doyle have been poached by the Baltimore Ravens and Atlanta Falcons. Then get into the movement of coaches and GMs around the league. Later, we get into the possibility of Giannis Antetokounmpo being traded to the Chicago Bulls, and the future of the Chicago Blackhawks and White Sox.

The Bears Staff Is Being Poached + How to Make Giannis Antetokounmpo a Chicago Bull

On today's episode of The Stretch, we get into a full recap of the best moments from the 2025 season. The best moments will be drafted in snake draft fashion and broken down. We are later joined by MikeyBets for a recap of "D-Rose Night" where Derrick Rose had the #1 retired by the Chicago Bulls, which leads us into a conversation of Chicago's teams banking off nostalgia.

Ranking Chicago's Best Moments From The 2025 Season + Retiring Derrick Rose's Number | FULL SEASON BREAKDOWN

On today's episode of The Stretch we recap the Chicago Bears playoff loss and season finale to the Los Angeles Rams. We get into the strange place we find ourselves where as Bears fans we never thought we would come this far, and the pain of losing after coming this far. We then discuss where this season ranks in how fun it was to watch and how hopeful we are for the future ahead of us.

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The Bears Season Is Over in Divisional Round, Was This The Most Fun Season of Our Lives? | 2025 Season Finale

Today we are bringing you a bonus episode of The Stretch, due to the first time in Barstool Chicago history that the Chicago Bears have won a playoff game. We get into some key match ups, the weather, and overall predictions for Bears vs Rams playoff game.

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The Stretch

The best Chicago sports podcast in history

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