There wasn't a Dallas Cowboys fan alive who wasn't hoping that Derrick Henry would have a star on the side of his helmet in the 2024 season. Unfortunately, Jerry Jones didn't quite see it that way. Instead of even a marginal effort to get the workhorse running back, he signed the walking dead crew of Ezekiel Elliott and Dalvin Cook to occupy the Cowboys backfield. Henry eventually landed with the Baltimore Ravens, and that's where he'll stay even longer after they signed him to a two-year extension on Wednesday.
It would've been one thing for Jones and the Cowboys to reach out to Henry and begin negotiations and not be able to align on a contract to close a deal. But the Dallas owner and the front office didn't even attempt it. Henry admitted as much, twisting the knife for fans as he said the Cowboys would've been a "perfect" match for him, but noted that they "never reached out".
Even in the immediate aftermath, that looked like a critical failure on Jones' part to not be aggressive in getting the best available player not named Saquon Barkley to fill a then-vacant backfield. It looked worse when the Cowboys landed their eventual options, which resulted in an entirely underwhelming performance on the field.
Now, after last season and enough faith from the Ravens to extend him with $25 million guaranteed and $15 million in average annual value on his new deal, the failure to pursue Henry looks even worse and only makes Cowboys fans even sicker to their stomach.
Derrick Henry extension is a painful reminder to Cowboys fans of Jerry Jones' biggest failure
While Dallas was mired trying to make it 2019 again with Zeke and Cook before eventually realizing Rico Dowdle was the only functional back on the roster, Henry was dominant alongside Lamar Jackson. Despite being 30 years old, he still rushed for 1,921 yards on 325 carries with an NFL-high 16 rushing touchdowns, not to mention his two receiving touchdowns as well.
That's why the Ravens felt comfortable giving Henry the extension. Make no mistake, there's risk involved. ESPN's Adam Schefter noted its the longest contract given out to a running back over 30 years old in NFL history, which makes sense given how players at the position normally age. Henry, however, is a different animal — if anyone's going to buck that trend, he's proven its him.
Coming into the NFL from Alabama, there were already concerns about his workload and him wearing down. He then went on to log more than 2,000 carries with the Titans and only missed more than two games once over eight seasons while also never averaging fewer than 4.3 yards per carry as the full-time starter.
Meanwhile, the Cowboys have continued to scramble to try and fix their running back issue. Bringing in Javonte Williams and Miles Sanders in free agency is better than Elliott and Cook, but still uninspiring. There's some buzz around fifth-round rookie Jaydon Blue as the potential next Tony Pollard but, even then, the upside probably isn't what Henry has continued to prove he's capable of.
So often, the refrain among Dallas fans is that this team has succeded in spit of Jerry Jones. There's no better recent example of this than missing out on Henry. Fans are optimistic about the 2025 season with the return of Dak Prescott and the arrival of George Pickens. At the same time, imagine how much more hopeful they'd be if Henry was involved. Jones failed to even get out of his chair to make that a possibility, which is a painful reality check that this franchise will continue to fight uphill battles as long as the current owner is manning the controls.