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Moments that shaped Tony Romo's career in Dallas

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Time on sideline helped Romo walk away (1:53)

Herm Edwards believes Tony Romo's time on the sideline played a major role in his decision to pursue broadcasting. (1:53)

Editor's note: This post has been updated to reflect Tuesday's news that Tony Romo is leaving football to pursue a job in broadcasting.

FRISCO, Texas -- Tony Romo, who arrived as an undrafted free agent from Eastern Illinois in 2003, has been among the NFL’s best quarterbacks for a decade.

News broke Tuesday that Romo is leaving football to pursue a career in broadcasting, so here are the 10 moments that shaped his career with the Cowboys:

1. The Speech

The moment: With the Cowboys in the midst of a eight-game winning streak last season, Tony Romo delivered the eulogy for his Cowboys’ career.

Why it mattered: Romo, who wrote the speech that lasted 5 minutes and 59 seconds, didn’t share it with anyone in the organization before delivering it from a lectern two days after Dak Prescott rallied the Cowboys twice in the final two minutes to beat the Pittsburgh Steelers. Romo said Prescott had earned the right to start for the Cowboys.

It was the ultimate team-first move because Romo, a starter since 2006, eliminated all of the controversy surrounding who should be the Cowboys’ quarterback.

Romo made it clear he wanted to play football again, but indicated he would accept the backup role and support Prescott.

2. The Botched Hold

The moment: Trailing 21-20 with 1:19 left, the Cowboys lined up for a 21-yard field goal attempt that would’ve given Dallas the lead in a 2006 NFC wild-card game against Seattle. Romo, the holder, bobbled the snap and was tackled short of the end zone trying to run for a touchdown.

Why it mattered: The botched field goal started the narrative of how Romo tends to make his biggest gaffes at the worst times.

The botched hold is why we don’t remember Romo driving the Cowboys from the Dallas 28 to the Seattle 2 in 2:59.

He completed 17 of 29 passes for 189 yards and a touchdown, but what we remember is Romo robbing the Cowboys of a chance to win a playoff game with an easy field goal.

More than a decade later, Romo remains synonymous with this play.

3. A Crazy Play

The moment: With 56 seconds left in the first half of a 2007 game against the St. Louis Rams, center Andre Gurode snapped the ball over Romo’s head. Romo finally scooped it up the Dallas 17 -- 33 yards from the line of scrimmage -- and ran 37 yards to the St. Louis 46 to get a first down.

Why it mattered: That play, four games into the season, epitomized Romo’s athleticism and ability to make big plays out of chaos.

It’s a trait he demonstrated countless times during his decade as a starter with the Cowboys. So many times, he looked like he was about to get sacked and he’d escape and throw a touchdown pass.

Those are the same traits that led to Romo making game-changing mistakes.

4. Mr. Tough Guy

The Moment: On the third play of a 27-24 overtime win over the San Francisco 49ers in 2011, linebacker Ahmad Brooks hit Romo, breaking two ribs and puncturing his lung. He missed virtually all of the third quarter, so the painkiller could kick in. He returned in the fourth quarter to rally Dallas from a 10-point deficit to win.

Why it mattered: Football is about toughness, and playing through pain and injury is revered.

For any player or fan who ever questioned his toughness, it was no longer an issue after that performance. It was the kind of performance that builds credibility in the locker room.

Romo passed for 345 yards, including a 77-yard OT completion that set up the game-winning field goal.

5. A Playoff Win

The moment: Trailing 14-0 in the first quarter of a 2014 NFC wild-card game, Romo rallied the Cowboys to just their second playoff win since 1996 with a touchdown pass to Terrance Williams with 2:32 left.

Why it mattered: Quarterbacks have always been judged by their playoff wins, whether it’s fair or not. The Cowboys had a team capable of advancing to the Super Bowl and to lose a home playoff game after a 12-win season and an NFC East title would’ve been devastating.

Instead, Romo found a way to win in the fourth quarter, notching just his second playoff win.

6. A Duel with Peyton

The moment: Romo passed for 500 yards and five touchdowns, but an interception late in the fourth quarter of this 2013 loss to the Denver Broncos ruined his performance.

Why it mattered: You could certainly argue this was the greatest game Romo ever played. And you also could argue this game is the epitome of his career.

After a flawless performance - he passed for 504 yards - in which he outdueled Peyton Manning, Romo needed one more scoring drive to claim a win.

Instead, his interception set up Denver’s game-winning field goal as time expired.

The narrative about end-of-the-game blunders continues.

7. A Trip to Cabo

The moment: The Cowboys finished 13-3 in 2007, winning the NFC East and earning a first-round bye. Romo, tight end Jason Witten and linebacker Bobby Carpenter spent a couple of days soaking up the sun in Cabo San Lucas, Mexico.

Why it mattered: The New York Giants, a playoff opponent the Cowboys had already beaten twice by 10 points, viewed the trip as a sign of disrespect.

Romo completed 18 of 36 passes for 201 yards with a touchdown and interception in the 21-17 loss.

Stacked on top of the botched hold in 2006, Romo was getting a reputation as a player who couldn’t handle the pressure of the playoffs. The trip to Cabo made some wonder if he cared enough about winning.

8. A Thanksgiving to Remember

The moment: Romo, an undrafted free agent, made his fourth career NFL start against the Tampa Bay Buccaneers in 2006 after replacing former No. 1 overall pick Drew Bledsoe. Most of the country never had heard of Romo. All they knew is that he was the guy former coach Bill Parcells chose to replace Bledsoe.

Why it mattered: This national TV game introduced Romo to America. He completed 22 of 29 passes for 306 yards with five touchdowns and a near-perfect passer rating of 148.9.

He showed every facet of his game - athleticism, accuracy and charisma - and just like that, Romo became a star as he won for the fourth time in five starts.

The comparisons to Roger Staubach and Troy Aikman started. That performance launched his career and earned him a trip to the 2006 Pro Bowl despite only starting 11 games.

9. Intestinal Fortitude

The Moment: Romo threw a career-high five interceptions and struggled in front of a national TV audience in this 2007 game on Monday Night Football against Buffalo. But he led the Cowboys to 10 points in the final 20 seconds and they rallied to beat the Bills.

Why it mattered: It’s not hard to find a quarterback who thrives when everything is going well. It’s a lot more difficult to find a quarterback with the temperament to forget three awful quarters of football and play his best in the fourth quarter.

Romo showed he could do that against Buffalo, and it served him well over the years.

10. A victory over undefeated New Orleans

The moment: The New Orleans Saints won their first 13 games in 2009, and the Cowboys were in the midst a two-game losing streak and their usual December swoon when the teams met in the Superdome.

Why it mattered: Romo played one of his best games passing for 312 yards a touchdown and outplaying Drew Brees. The Cowboys grabbed a 14-0 first quarter lead and won 24-17.

The victory started a three-game winning streak to end the season, propelling the Cowboys into the playoffs. The end-of-the-season momentum resulted in a 34-14 first-round playoff win over Philadelphia, the first of Romo’s career.