Romo worth $108M? Best, worst moments of Cowboys QB's career

If you haven't heard, the Cowboys have added six-years and $108 million to Tony Romo's contract. Is Romo worth it or did Jerry Jones just sign the Cowboys up for six more years of mediocrity?

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Let's take a look at our list of the three best moments and three worst moments of Tony Romo's star-crossed career.

Top 3 worst moments

1. 2006 playoffs: Besides Dan Marino's ill-fated 'laces out' hold for kicker Ray Finkle in the movie Ace Ventura, there may be no bigger botched hold in football history than Romo's in the Wild Card playoffs following the 2006 season. Cowboy fans know the situation by heart, but for everyone else, lets rehash: with 1:19 left in the fourth quarter and the Cowboys trailing the Seahawks 21-20, Dallas lined up for a 19-yard field attempt that would have given the Cowboys the lead. However, kicker Martin Gramatica never got to try the kick because Romo didn't get the hold down. Romo bobbled the snap and was forced to try and run it in for a score, but he didn't make it to the end zone and the Cowboys were sent packing. 

2. The Jessica Simpson playoff game: After the botched hold against Seattle, Romo's next chance to get a playoff win came after the 2007 season against the Giants. The Cowboys had swept the Giants in the regular season and earned the NFC's No. 1 overall seed, so Dallas got a bye week before meeting New York in the Divisional round. How Romo spent that bye week became a sensitive topic in Dallas. While the Giants spent Wild Card weekend beating the Buccaneers, Romo decided to jet off to Los Cabos, Mexico with then-girlfriend Jessica Simpson. This didn't turn out good for anyone. The Cowboys lost to the Giants. Tony and Jessica eventually broke up and Los Cabos was hit by a hurricane nine months later. 

3. Redskins-Cowboys 2012 regular season finale: This may not be the third worst moment in Romo's career, but it's on the list because its the most recent and it does a good job of epitomizing Romo's almost innate ability to struggle in big games. In the final game of the 2012 season, all the Cowboys had to do to make the playoffs was beat Washington. Long story short: Dallas lost and Romo threw three interceptions. The loss to the Redskins came on the heels of similar situations in 2011 and 2008 when the Cowboys missed the playoffs after losing their final regular season game. 

Top 3 best moments

1. Romo finally gets a playoff win: They say the third time's a charm and that was the case for Romo. In his third career playoff game, Romo finally got the postseason monkey off his back with a 34-14 win over the Eagles in the Wild Card playoffs following the 2009 season. Romo threw for 244 yards and two touchdowns and at one point led the Cowboys on five straight scoring drives. 

2. Romo leads comeback over 49ers after fracturing rib: In a fourth quarter comeback win over the 49ers, Romo proved that he can play injured and be clutch while he plays injured. With the Cowboys trailing San Francisco 24-14 on the road, Romo led Dallas to 10-points in the final 6:55 to send the game to overtime. On the Cowboys first offensive play of overtime, Romo threw a 77-yard pass to Jesse Holley that setup a Dan Bailey game-winning 19-yard field goal. Romo threw for 345 yards and two touchdowns against a 49er defense that would finish the season ranked fourth in the league. Romo actually left the game in the third quarter after fracturing his rib, but returned to lead the comeback. 

3. Romo throws for 416 yards and four touchdowns: One of the problems for Dallas during Romo's career has been that Romo's best moments aren't always the Cowboys moments. Take for instance Week 15 in 2012. Romo threw for 416 yards and four touchdowns along with no interceptions, only to watch the Cowboys lose 34-31 to the Saints. Romo has thrown for over 370 yards six times in his career, the Cowboys are 0-6 in those games. 

Keep your eye on everything NFL by following John Breech on Twitter: @JohnBreech.

CBS Sports Writer

John Breech has been at CBS Sports since July 2011 and currently spends most of his time writing about the NFL. He's believed to be one of only three people in the world who thinks that Andy Dalton will... Full Bio

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