Rich Eisen’s Choice Exposes Shocking Parallels Between Chargers and Cowboys

It is that time of the NFL calendar year when teams are catching their last breath between OTAs and the start of training camp. The Chargers will return for training camp in late July with rookies reporting on July 23rd and veterans reporting five days later on the 28th.

This time of year makes stories and content hard to come by for national sports media unless there is a very public dispute or wild legal trouble hitting the breaking news wire. Several shows and hosts have built-in downtime killers in their regular programming.

The Rich Eisen Show hosted by Rich Eisen is a long-running daily national sports show airing on television and radio. The show has a segment called "What's more likely." Eisen was given a question during this segment that has roots deeper than originally thought.

Eisen was presented the question over which "much maligned" quarterback would reach a Super Bowl first in 2026, Justin Herbert and the Chargers or Dak Prescott and the Dallas Cowboys. He picks Herbert and jokingly says "Harbaugh over the Cowboys any day of the week."

Rich Eisen picks Justin Herbert over Dak Prescott to reach a superbowl first. pic.twitter.com/4AuD68Ufdl
— Thomas Martinez (@BoltsDraftTalk) June 29, 2026

The argument for Herbert over Prescott this season makes sense given the makeup of both teams, the arrival of Mike McDaniel and the excitement associated with the Chargers. The Cowboys, with a beefed up defense could make a case for Dak. Obviously, this is just a hypothetical question framed as which would be more likely and in theory, both Herbert and Prescott could reach the Super Bowl and face each other at the end of this season.

A bigger question can be raised from the question of Herbert versus Prescott. Should the Cowboys and Chargers be compared to each other more often?

The NFL is a "What have you done for me lately" league but both franchises have had similar successes and issues over the past 30 years or so. Comparatively, the two teams are mirror images of each other in opposite conferences.

Chargers and Cowboys team success comparison since last Super Bowl appearance. | Thomas Martinez

The Chargers and Cowboys have both been off-season darlings many times over. The Chargers and Cowboys have had franchise quarterbacks for years in Philip Rivers and Tony Romo before Herbert and Prescott. Both franchises have suffered terrible luck in key moments in the playoffs whether it was the Chargers with the Marlon McCree fumble in the 2006 divisional round or the Cowboys with Dez Bryant's non-catch in 2014 divisional round.

Which one of these two teams will finally get over the hump that seems to be haunting both franchises since their last Super Bowl appearance? Both have franchise quarterbacks in their prime and are pushing from opposite sides of the ball to clear the hurdle.

The Chargers have revamped their offense this off-season with the hiring of new offensive coordinator Mike McDaniel and the installation of a new wide-zone rushing attack that is perfectly suited for running back Omarion Hampton. The passing game is being revamped to directly counter the Chargers' shortcomings the past two years in the playoffs.

The focus in the passing game is shifting for Justin Herbert to get rid of the ball quickly with anticipation to give receivers more opportunities for yards after the catch and explosive gains. The quick game is also going to help limit the opposing pass rush, something that has plagued the Chargers offensive line in January.

The changes the Chargers have made give hope to make Rich Eisen's prediction and choice of Herbert and the Chargers reaching a Super Bowl. The Cowboys have made changes to their defense and could help Dak Prescott finally get there as well.

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