I woke up this Sunday morning having dreamt that I was fired from my job with no explanation at all. This is a job that I’ve had for the past 17+ years so it came as a shock.

Luckily it was just a dream, but I still have this sense of worry in my gut for no legitimate reason except the lingering feeling of loss.

This is also how I feel every year the Dallas Cowboys get bounced from the playoffs way earlier than any of us expected. That’s happened a little too often over the years.

I saw a question on Twitter/X posed by Cowboys fan and Inside The Star alumni Jess Haynie. Jess posed a good question that got me thinking.

Jess says, “In terms of talent and not where they finished, which (Dallas Cowboys) roster over the last 10 seasons (2014-2023) do you feel was closest to winning the Super Bowl?”

Wow, Jess what a great question. Instead of analyzing every season since 2014, I decided to just rank the top three teams in that span with Super Bowl aspirations.

Let’s be real here. It’s the Dallas Cowboys. There are Super Bowl aspirations every season but today we are really going to focus on the teams who had a legitimate shot at the big game.

3. Green Bay Strikes Again

I want to start with the most recent season at number three. The 2023 NFL season was a rollercoaster ride for Cowboys fans.

Dallas finished the season as the #2 seed, tied with the San Francisco 49ers and Detroit Lions with 12-5 records. The Cowboys lost the head-to-head tiebreaker with San Francisco but won the same tiebreaker versus the Lions.

QB Dak Prescott finished 2nd in MVP voting and arguably should have won the award but that’s the price you pay when you wear The Star.

The Cowboys entered the season with depth concerns at linebacker and running back, and at least one of those could have cost them their season.

Dallas dominated opponents at home, going undefeated in Arlington and averaging a shade over 37 points per game. Every home game except versus Detroit (20-19) and Seattle (41-35) resulted in a blowout.

When it came time to show up in the playoffs, however, Dallas disappointed yet again with a flat and uninspired performance.

Not only did they lose to the Packers AGAIN, but they were absolutely embarrassed. At one point in the 4th quarter, they trailed by the score of 48-16.

There’s no telling whether the Cowboys could have made it past the 49ers to advance further, but we will never know thanks to that lackluster performance.

2. Rookie Tandem Leads the Way

The 2016 season was another magical season for the Cowboys and their fans that ended in heartbreak.

This season was unique because the top performers on offense at the skill positions were both rookies. 2016 was the year QB Dak Prescott and RB Ezekiel Elliott were drafted and they took the league by storm.

No one knew it at the time, but when Tony Romo went down in that preseason game at Seattle, it marked the start of a new era at quarterback for the Cowboys.

Backup Kellen Moore was also injured, and it opened the door for a rookie Prescott to take first-team reps. He never looked back.

Prescott lost his first NFL game due to a bone-headed play by WR Terrance Williams. With Dallas nearly in position for a game-winning field goal attempt by Dan “Mr. Automatic” Bailey, Williams caught a pass and turned upfield instead of out of bounds.

Dallas had no timeouts and the clock ran out. After that loss and powered by a powerful running game behind the league’s best offensive line opening lanes for Elliott, Prescott led the Cowboys to 11 consecutive wins.

They finished the season atop the NFC, but after a 1st round bye, the Boogeyman Aaron Rodgers and the Packers would send the young Cowboys packing after a 53-yard Mason Crosby field goal made its way through the uprights.

Green Bay would move on to the NFC Championship Game in Seattle. Dallas had already defeated the Seahawks in Seattle during the regular season.

The 3rd & 20 completion from Rodgers to TE Jared Cook right on the sideline to set up Crosby for the winning field goal will always haunt me.

1. Dez Caught It

Do I even need to write anything in this section? I know Dez caught it. You know Dez caught it. Dean Blandino knows Dez caught it. I believe if the game was in Arlington, the call would have gone the other way.

Nobody knew at the time but the 2014 season would be Tony Romo’s last full season as a starter. He was injured and lost for the season in 2015 before the last fateful injury in the 2016 preseason.

Dallas ran through the league in 2014 behind the best offensive line in football leading the way for the league’s leading rusher, DeMarco Murray.

Murray finished the year with a franchise record 1,845 yards rushing and 13 touchdowns. The elite rushing attack can be attributed to the Cowboys drafting the last link, Zack Martin, to play right guard.

It solidified the line and a rushing attack that would lead the Cowboys into the playoffs, where they would once again fall to Aaron Rodgers and the Packers.

This Cowboys team was the best-built team that I had seen since the 2007 squad, and it also finished atop the NFC after the regular season.

Romo played the best season of his career in 2014 and he should have been rewarded with a Super Bowl appearance against the immortal Tom Brady and the Patriots.