The Cowboys Odyssey: Every challenge standing between Dallas and Super Bowl LXI
Odysseus waited 20 years to return to his home. The Dallas Cowboys have been waiting 30-plus years to be in the Super Bowl again. Let’s dive into what their 2026 journey could look like.
I promise no movie spoilers lie ahead (other than references to Homer’s classic story because, you know, it’s over 3,000 years old) but let me tell you: I loved Christopher Nolan’s The Odyssey and I didn’t even watch it on IMAX (but I’m definitely planning on making a trip to do so).
And one feeling that it left me with that I’ll always remember is “Woah, all that happened in one journey?”
The problem is, the Dallas Cowboys can only escape my mind for so long, so I thought it would be a good idea to talk about their own Odyssey to a a sixth Super Bowl victory. Unlike Odysseus’ journey to Ithaca, the Cowboys aren’t heading home. But they’re aiming toward something they haven’t achieved in three decades. It won’t be easy, as many challenges (and mighty foes) lie ahead.
So while we wait for training camp, let’s look at what stands between the Cowboys and raising the Lombardi Trophy.
Weeks 1-2: Starting the journey
- @ New York Giants
- vs Washington Commanders
Like when you boot up a videogame, these seem like the early levels. In other words, these are very winnable games for the Cowboys and I bet they’ll be favorites entering each.
But while the Giants and the Commanders did poorly last season, they should be significantly improved. Like in Homer’s Odyssey, we won’t have to wait too long for monsters to appear. The Giants’ pass rush is filled with threats, including Abdul Carter, Brian Burns, and Kayvon Thibodeaux. The Giants may have a roster with many flaws, but this could be one of the best units in all of football.
From the start of the season, the Cowboys pass protection, particularly at offensive tackle, will be a major storyline. That’s why I worry about Tyler Guyton’s development in camp and consider him the most important Cowboy to watch in Oxnard, California.
As for the Washington Commanders, the Cowboys will be entering a mysterious island. Jayden Daniels is a powerful foe, the question is if he’ll have enough help beyond WR Terry McLaurin.
Weeks 3-7: Finding out who the Cowboys are
- vs Baltimore Ravens (Rio de Janeiro, Brazil)
- @ Houston Texans
- vs Tampa Bay Buccaneers (on a short week)
- @ Green Bay Packers
- @ Philadelphia Eagles
In The Odyssey, there are many instances where Odysseus and his crew are tested. This stretch of games will be exactly that for the Cowboys. These are quality foes that were all in the playoffs last year, except for Tampa Bay (the one team you get on a short week).
In Lamar Jackson, the Cowboys defense will find its first elite quarterback test. Something to watch will be the linebackers against Jackson’s legs. This feels like the first game that will give us a direct gauge of Christian Parker’s defense.
Then you get the Houston Texans, whose defense carried them to a 12-win record and could be one of the NFL’s best teams if quarterback C.J. Stroud bounces back. Parlay that with a short week against the Bucs being followed by a couple of NFC contenders in the Packers and Eagles.
At Lambeau, the Cowboys are likely to play Micah Parsons in his return from injury and later, the Eagles’ high-powered defense will have home-field advantage against Dallas.
In the classic Odyssey, the most devastating scene comes when the giant Laestrygonians destroy most of Odysseus’ fleet. These five games represent the Laestrygonians to me, with my question being: Will the Cowboys survive the relentless attack? Or will the playoffs be a long shot dream after such a difficult start to the season? By the time Week 7 is over, we’ll know a lot about this football team.
Weeks 8-11: Strengthen up
- vs Arizona Cardinals
- @ Indianapolis Colts
- vs San Francisco 49ers
- vs Tennessee Titans
In the NFL, there’s no such thing as an easy opponent, but this is the most forgiving stretch on the Cowboys schedule. The Cardinals and Titans should both be significantly outmatched in talent by Dallas.
Meanwhile, the Colts and 49ers are very worthy opponents since they have complete rosters but these look like toss-up games for me at most. I give the edge to the Cowboys as of today thanks to them having an elite offense (even if it’s on paper for now).
Weeks 12-16: Monster season
- vs Eagles
- @ Seahawks
- BYE
- @ Rams
- vs Jaguars
You get all sorts of creatures in The Odyssey but perhaps none is scarier than what the Rams are likely to show in Week 15: a two-headed monster in Myles Garrett and Aaron Donald (who is pondering a return to playing).
The Cowboys offensive line will face its major test if that comes to fruition. Prior to that, the Cowboys will take on the Eagles and Super Bowl-champion Seahawks in a 10-day span. To close things out, they’ll get Trevor Lawrence to challenge their secondary at AT&T Stadium.
When it’s all said and done, this may be the stretch of games that officially defines if the Cowboys are headed to the postseason or not.
Weeks 17-18: Closing time
- vs New York Giants
- @ Washington Commanders
Talk about getting cinematic. Right before the postseason, we get a flashback to where it all began! Nolan would love this, actually…
The Cowboys playoffs
There’s one theme that’s followed the Cowboys all offseason long and it’s been the rebuilding of the defense, which was the league’s worst in 2025. I have little doubt the Cowboys can have a winning record in the regular season even without the defense being a standout unit this season.
But in the past, playoff offenses have been the undoing of the Cowboys. Consistently so. In the final stages of their Odyssey, the Cowboys will have to prove they can fend off the efforts of legendary quarterbacks like Matthew Stafford and terrifying armies like the Seahawks’ defense.
Maybe, just maybe, it can be a successful journey after a 30-year wait.
“The trial is not over yet,” says Odysseus near the end of Homer’s classic.
