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In February 2020, Romo renewed his contract with CBS through at least 2022, with the network reportedly paying him $17 million per-year—which would make Romo one of the highest-paid personnel in sports broadcasting and "the highest-paid NFL analyst in television history."

Romo and Nantz received further acclaim for their broadcasting of the 2018 AFC Championship Game between the Kansas City Chiefs and New England Patriots, as "Nantz continually set Romo up to make his predictions and analysis prior to the snap", and some suggested that Chiefs head coach "Andy Reid could have used Romo on his defensive staff, because the former quarterback knew just about every play the Patriots were going to run down the stretch." According to The Guardian, the "beauty of Romo's analysis is that it feels like he's in on the fun with you." Romo and Nantz called Super Bowl LIII in Atlanta.

Although Cowboys owner Jerry Jones initially said Romo would remain the team's starter when he returned, Prescott's success with the team and the length of Romo's injury led to Jones reconsidering his decision. Amid Prescott guiding the team to an eight-game winning streak, Romo conceded his role as starting quarterback to Prescott and began serving as the Cowboys' backup when he returned to the active roster in Week 11. Romo made his season debut in the regular season finale on January 1, 2017, against the Philadelphia Eagles. In what would prove to be the final play of his career, he threw a touchdown pass to Terrance Williams before Mark Sanchez played the rest of the game.

On April 4, 2017, Romo announced his retirement from the NFL. After announcing his retirement, he was released by the Cowboys, per his request. Following his retirement, Dallas Mavericks owner Mark Cuban announced that Romo would be a "Maverick for a day" for the Mavericks' final home game of their 2016–17 season. He warmed up with the team and sat in full uniform on the bench, but did not play in the game and was not considered an official member of the roster.

Once the 2017 NFL season got underway, Romo received critical praise for his work as a recent ex-player, most notably for his ability to predict offensive plays and read defensive formations from the booth, and "adding an enthusiasm that had been lacking with Simms."

Romo was unable to start in the 2016 regular season after suffering a compression fracture to the L1 vertebra in his back during the Cowboys' third preseason game against the Seattle Seahawks. The injury caused him to miss the first 10 games of the season, with the duties of the team's starting quarterback being assumed by rookie Dak Prescott.

Romo led the NFL in completion percentage and passer rating en route to the NFC East title, and he was ranked 34th in the NFL's list of the top 100 players of 2015, the highest undrafted player on the year's list.

Romo started strong in the 2015 season, throwing a game-winning pass to Jason Witten with seven seconds left in the Cowboys' season opener against the New York Giants. He continued to show success in a week 2 victory over the Philadelphia Eagles, but suffered a broken left collarbone in the third quarter after being sacked by linebacker Jordan Hicks. The injury sidelined Romo for eight weeks, during which the Cowboys failed to win a single game with Brandon Weeden and then Matt Cassel starting at quarterback.

On November 29 against the Green Bay Packers, in a game between 10–1 teams, Romo threw four touchdown passes (bringing his season total to 33), breaking Danny White's (29) record from 1983. On December 22 against the Carolina Panthers, Romo became the first Cowboys' quarterback to pass for more than 4,000 yards in a season. Finally on December 30 against the Washington Redskins, Romo broke the Cowboys' season completions record with his 335th completion, a short pass to tight end Jason Witten. The Cowboys finished the season with a 13–3 record.

On September 15, Romo led the Dallas Cowboys to a 41–37 win against the Philadelphia Eagles in the second game of the 2008 season. Romo completed 21 of his 30 passes for a total of 312 yards and three touchdowns. The 54 combined points scored by the Cowboys and Eagles in the first half were the second most points scored in a half during a Monday Night Football game. That same month, Romo signed a 5-year, $10 million endorsement deal with apparel marketer Starter, but was not allowed to wear footwear on the field as the company did not have a contract with the NFL.

Romo and the Cowboys won their third straight before losing to the Washington Redskins, falling to 3–1. Following a win against the Cincinnati Bengals, Romo was injured in a loss to the Arizona Cardinals. The Cowboys, under Brad Johnson, went 1–2 the next three games, falling to the St. Louis Rams, beating the Tampa Bay Buccaneers, and losing to the New York Giants.

In what became a de facto third playoff game for Romo shortly prior to its start, on December 28, Romo and the Cowboys failed to compete against the Philadelphia Eagles in a 44–6 loss. Romo committed three turnovers in the game and went 21/39 for 183 yards and no touchdowns. The loss dropped Romo's combined record in December to 5–8 and again raised questions about his performance in games of consequence.

Romo led the Cowboys to a 34–21 win over the Tampa Bay Buccaneers in their season opener. He completed 16 of his 27 passes for a then-career-high 353 yards along with three touchdowns.

Romo had a 104.9 passer rating in a 34–14 win of the Philadelphia Eagles in the first round of the playoffs, earning the first play-off win in 13 years for the Cowboys, and his own first career post-season win.

However, the following week in the NFC Division Round against the number two seed Minnesota Vikings, Romo had three fumbles (losing two), an interception and was sacked six times in the 34–3 loss.

In Week 5 against the Tennessee Titans, Romo threw for a career-high 406 yards and three touchdowns. However, he also threw two costly interceptions in the fourth quarter, resulting in 34–27 loss at Cowboys Stadium. Romo and the Cowboys were desperate for a win with a record of 1–3 and last in the division. They played against the Minnesota Vikings, who also had a 1–3 record and were in need of a win. Romo threw for over 200 yards and 3 touchdowns but also threw two costly interceptions. The Cowboys lost the game by a score of 24–21.

In Week 16 against the Philadelphia Eagles, Romo suffered a severely bruised hand when he smashed it against an opposing player's helmet. He left the game after attempting just two passes with no completions. The next week, in the season finale at MetLife Stadium against the Giants, the NFC East title and a playoff spot was at stake for whichever team won, with the loser eliminated from playoff contention. Romo started the game despite the hand injury the previous week. He posted 29 out of 37 passing for 289 yards, two touchdowns and one interception for a 106.0 QB rating and a 78% pass completion rate (second highest of the season) as the Cowboys lost the game 31–14, dropped to an 8–8 record and were eliminated from playoff contention.

After trailing the Cincinnati Bengals 19–10 with 6:35 left, Dallas beat Cincinnati 20–19 in Week 14 (December 9). The fourth quarter comeback consisted of a 27-yard touchdown pass from Romo to Bryant and a last-second 40-yard field goal by Bailey. Romo went 25-for-43 for 268 yards, with one touchdown and one interception.

Topping a three-game winning streak and winning its fifth out of six games, Dallas beat the Pittsburgh Steelers 27–24 in overtime in Week 15 (December 16). The win put Dallas in a three-way tie with New York and Washington in the NFC East. Romo surpassed 25,000 career passing yards in this game with 30-for-42 passing for 341 yards and two touchdowns.

The Cowboys signed Romo to a 6-year extension worth $108 million, with 55 million guaranteed and $25 million in bonuses, thus securing him for the rest of his career and relieving the pressure from the salary cap, which was reported to have less than $25,000 space before the deal was struck. In the middle of April 2013, he underwent back surgery to remove a cyst. Although it was characterized as a minor procedure by the team, he would end up missing all of the mini-camp and organized team activities.

In Week 16, against the Washington Redskins, with the Cowboys trailing in the fourth quarter and needing to win to keep its playoff hopes alive, he led the team to a touchdown drive with 1:08 remaining in a 24–23 victory, with what was later diagnosed as a season-ending herniated disk injury. Head coach Jason Garrett would later say: "He might have had his finest hour … We talk about mental toughness, being your best, regardless of circumstances. Somehow, some way, he helped us win that ballgame."

Romo underwent back surgery on December 27, 2013, and was placed on the Cowboys' injured reserve list. Garrett announced that Kyle Orton as the starting quarterback for the Week 17 game against the Philadelphia Eagles, which the team lost 24–22, to miss the playoffs for a fourth straight year.

After a poor performance in the season opening 28–17 loss versus the San Francisco 49ers, Romo and the Cowboys won six consecutive games, including back-to-back road games against the Tennessee Titans and the St. Louis Rams. The Cowboys also defeated the defending champion Seattle Seahawks on the road, becoming only the second team to win a road game against the Seahawks in the three seasons. Through those six wins, Romo had a 13:3 touchdown:interception ratio. In Week 8, a Monday night game against the Washington Redskins, Romo went down with a back injury when linebacker Keenan Robinson sacked him, with his knee going into Romo's back. After the loss to Washington, it was revealed that Romo had two fractures in his transverse process. He missed the next game, a 28–17 loss to the Arizona Cardinals, but came back the next week and went on to lead the Cowboys to a 12–4 record and their first divisional title since 2009.

On December 21, Romo set the Dallas Cowboys team record for highest completion percentage in a game with 90%, completing 18 of his 20 passes in a 42–7 blowout win over the Indianapolis Colts. He also set his personal best quarterback rating in a single game with 151.7.

In the wild card round of the playoffs, Romo led the Cowboys to a 24–20 comeback victory over the Detroit Lions after being down 17–7 at halftime. Romo was 19-of-31 for 293 yards with two touchdowns and no interceptions.

In the divisional round of the playoffs, Romo and the Cowboys were defeated by the Green Bay Packers, 26–21. Romo was 15-of-19 for 191 yards with two touchdowns and no interceptions.

Romo returned to the starting lineup in a week 11 game against the Miami Dolphins. Despite throwing two interceptions, he completed 18 of 28 passes for 227 yards and two touchdowns in a 24–14 victory, ending the Cowboys' seven-game losing streak.

The Cowboys then faced the 10–0 Carolina Panthers in a week 12 Thanksgiving game. Although up against an undefeated team and holding only a 3–7 record, the Romo-led Cowboys were favored to win and still had hopes for the playoffs in a weak NFC East division. However, Romo threw three interceptions in the first half, two of which were returned for touchdowns, helping the Panthers take a 23–3 lead. At the end of the third quarter, Romo was sacked by linebacker Thomas Davis, reinjuring his left shoulder and ending his season. Romo remained on the active roster until December 21 when he was placed on injured reserve after the Cowboys dropped to 4–10, officially ending their playoff hopes.

While there was no controversy of Romo deciding to retire and move on to broadcasting, some critics questioned Romo being immediately hired for the number one position ahead of broadcasting veterans Dan Fouts, Trent Green, or Rich Gannon, all of whom served in the number 2–4 positions respectively for CBS, with Fouts having once been the color commentator on Monday Night Football. While some critics had speculated that Romo was handed the top position so quickly because he wore a star on his helmet, other reports cited CBS having grown tired of Simms in the role, which was a mutual feeling by Simms himself. Nonetheless, none of the ex-players and coaches in a lead position on other networks at the time of Romo's hiring (Troy Aikman, Cris Collinsworth, and Jon Gruden) started their broadcasting career in the lead position. Simms jokingly asked Romo "How does that seat feel?" during Week 1 of The NFL Today.

As of 2013, Romo hosted a youth football camp in Burlington, Wisconsin, annually during the summer, since 2004. In the Dallas area, Romo participated in community activities in collaboration with United Way, the Make-A-Wish Foundation, and the Society for the Prevention of Cruelty to Animals.

Daniel Jeremiah, an NFL.com analyst, ranked Romo as the 9th best quarterback in the league heading into the 2012 season. The controversial 2012 NFL Top 100 ranked Romo as the 12th best quarterback in the league going into the 2012 season.

However, Dallas finished 2012 with an 8–8 record and failed to make the playoffs for the third straight season after losing the last two games. On Week 16 (December 23), despite Romo's four touchdown passes and 416 passing yards (on 26-for-43 passing), Dallas lost to New Orleans Saints, 37–34, in overtime. Following that game, Dallas and the Washington Redskins had a two-way tie of 8–6 records atop the NFC East, and faced each other in Week 17 for the NFC East title, which Dallas lost, 28–18. With overall 20-for-37 passing, Romo threw a total of three interceptions, including on Dallas' first two drives. With 5:50 left and down 21–10, Romo made a touchdown pass to Kevin Ogletree and two-point conversion pass to Dwayne Harris. After Dallas took over with 3:33 left down 21–18, Romo threw an interception to Redskins linebacker Rob Jackson, and Washington clinched the victory with another touchdown.

Romo's 102.5 QB rating in 2011 was fourth best in the league behind Aaron Rodgers, Drew Brees and Tom Brady, and second highest in Cowboys history.

Romo had four fourth-quarter comebacks in 2011 and had a would-be game-winning field goal attempt against the Arizona Cardinals and a would-be game-tying field goal attempt against the New York Giants both blocked (The Cowboys lost both of those games).

Romo accounted for 32 of the 39 total touchdowns the Cowboys scored in the 2011 NFL season (82.1%). No other player in the 2011 regular season contributed a higher percentage of team touchdowns (Cam Newton with 72.9% was second).

On May 28, 2011, Romo married Candice Crawford, the 2008 Miss Missouri USA, a former journalist for Dallas television station KDAF, and the sister of actor Chace Crawford. They had dated since the summer of 2009, and became engaged on December 16, 2010. The couple have three sons together: Hawkins Crawford Romo (born April 9, 2012) Rivers Romo (born March 18, 2014) and Jones McCoy Romo (born August 23, 2017).

During the October 25, 2010, Monday Night Football game against the New York Giants, Romo suffered a broken left clavicle. The injury occurred during the second quarter, when Romo was driven to the turf by Giants linebacker Michael Boley. He was placed on Injured Reserve on December 21, 2010, and replaced by veteran Jon Kitna.

During homecoming weekend on October 17, 2009, Eastern Illinois University retired Romo's No. 17 jersey and inducted him into EIU's Hall of Fame. Romo is the first Eastern Illinois player to have his number retired. He said of the event, "It was such an honor to be inducted into the Hall of Fame here, and with the jersey ceremony, it holds a special place in your heart."

In week 15, Romo led the Cowboys to a win against an undefeated team late in the season for the second time in his career. In 2006, he won against the 10–0 Indianapolis Colts, and on December 19, 2009, he defeated the 13–0 Saints at New Orleans, throwing for 312 yards, one touchdown and no interceptions.

Romo finished the 2009 season as the first quarterback in team history to take every snap for a full season. He also passed his own mark for single season passing yardage, with 4,483 yards, and became the first Cowboys quarterback to throw more than 20 touchdowns and fewer than ten interceptions in a season. His eight 300 yard games was also a team record, surpassing his own record from 2007. His 1.6% interception percentage tied a team record, and his career interception percentage became the lowest in franchise history.

In the Cowboys' January 13, 2008, divisional playoff game against the New York Giants, Romo was unable to lead his team to a come-from-behind victory. On fourth down with less than half a minute and no timeouts left, Romo threw the ball into the end zone, but it was intercepted by Giants cornerback R. W. McQuarters, ensuring that the Cowboys were eliminated from the playoffs with a 21-17 loss to the eventual Super Bowl XLII champions.

On September 7, 2008, Romo led the Cowboys to a 28–10 win over the Cleveland Browns in their season opener. Romo completed 24 of his 32 passes for a total of 320 yards and one touchdown. After the game, Romo required 13 stitches for a large gash on his chin that occurred during the third quarter when linebacker Willie McGinest hit him in the chin with his helmet. The NFL fined McGinest $7,500 for the hit.

The Cowboys played the Seattle Seahawks in the NFC Wild Card playoff round on January 6, 2007. With the Cowboys trailing 21–20 on fourth-and-one with 1:19 left in the game, the Cowboys attempted a 19-yard field goal. Romo, the holder for the kick, fumbled the snap. He recovered the ball and attempted to run it in, but was tackled short of the first down marker, and turned the ball over on the Seattle 2-yard line. The Cowboys went on to lose the game. Romo finished the 2006 season ranked seventh in the NFC in passing yards (2,903) and touchdown passes (19).

Romo played in the 2007 Pro Bowl after Drew Brees went down with an elbow injury as a substitution for Marc Bulger. He threw one touchdown and one interception, and was the NFC's kickoff holder in the game.

Romo began the 2007 season with four touchdown passes and an additional touchdown rush, the first of his career, defeating the New York Giants 45–35 in the Cowboys' first game of the regular season, His 345 passing yards in Week 1 led the NFL. In Week 2, he threw for 186 yards and two touchdowns beating the Miami Dolphins, ranking him seventh in passing yards and tied for second with six touchdown passes. Romo added 329 passing yards and two touchdown passes in the Cowboys' Week 3 34–10 win over the Chicago Bears. The following week, he passed for 339 yards and three touchdowns in a 35–7 win over the St. Louis Rams. He also ran for an additional touchdown. This brought his season totals to 1199 passing yards with 11 passing touchdowns and two rushing touchdowns. In September 2007, Romo's father was diagnosed with prostate cancer. Romo stated that, while upset about the family crisis, he still had to continue to focus on his career.

In November 2007, Romo began dating American singer and actress Jessica Simpson. On December 16, 2007, Simpson attended a Dallas Cowboys–Philadelphia Eagles game at Texas Stadium, in which Romo had a bad performance in the loss to the Eagles. Controversy erupted before the playoff game against the New York Giants—a game the Cowboys would lose—when pictures surfaced of Romo (along with teammates Jason Witten and Bobby Carpenter) at a resort in Cabo San Lucas with Simpson. On July 13, 2009, People reported that Romo and Simpson had broken up on July 9, 2009—the night before her 29th birthday.

Romo holds several Cowboys team records, including passing touchdowns, passing yards, most games with at least 300 passing yards, and games with three or more touchdown passes. He also held a higher passer rating in the fourth quarter than any other NFL quarterback from 2006 to 2013. However, Romo's reputation was affected by a lack of postseason success, having won only two of the six playoff games he appeared in and never advancing beyond the divisional round. His 97.1 passer rating is the fourth highest of all time and the highest among quarterbacks not to reach the Super Bowl, as well as the highest among retired players.

One week later on October 23, 2006, Romo replaced Bledsoe for the start of the second half of a game against the New York Giants. His first pass was tipped and intercepted. His game stats in only his second NFL appearance were 14 completions on 25 attempts for 227 yards, two touchdowns, and three interceptions (one of which was returned for a touchdown). On October 25, Cowboys head coach Bill Parcells announced that Romo would be the Cowboys starting quarterback for the October 29 game against the Carolina Panthers on NBC Sunday Night Football, in Week 8 of the 2006 season. Romo led the Cowboys to victory in his first game as a starter, 35–14. In that game, Romo was Sunday Night Football's "Rock Star of the Game."

On November 19, 2006, Romo led the Cowboys past the Indianapolis Colts, the NFL's last unbeaten team. He completed 19 of 23 passes as the Cowboys won against the Colts 21–14. Four days later he helped the Cowboys win in a Thanksgiving Day game against the Tampa Bay Buccaneers by the score of 38–10. Romo went 22–29 with 306 yards and five touchdown passes and no interceptions. For his performance, he was awarded FOX's Galloping Gobbler award as the Thanksgiving Day MVP.

After several kicks were missed by kicker Nick Folk due to bad holds by punter Mat McBriar, Romo resumed holding duties for the first time since the 2006 in their 13th game of the season, versus the San Diego Chargers.

In Week 10, Romo posted the second highest QB rating of his career with a rating of 148.40 (on November 23, 2006, Romo posted a rating of 148.90).

One of Romo's early career highlights was in 2004, when (as the third-string quarterback) he rushed for the winning touchdown with six seconds left in a preseason game against the Oakland Raiders. Elevated to the Cowboys' second quarterback in 2005, Romo had strong showings in the 2005 and 2006 pre-seasons. In the 2006 off-season, Sean Payton (now head coach of the New Orleans Saints), offered a third-round draft pick for Romo, but Cowboys' owner Jerry Jones refused, asking for no less than a second-round draft pick.

Romo is an avid amateur golfer, and attempted to qualify for the 2004 EDS Byron Nelson Championship and the 2005 U.S. Open, but failed. During the offseason, when not training, he plays golf around Dallas. He failed to make the cut in qualifying for Byron Nelson in 2008. In February 2018, it was announced that he had received a sponsor's exemption to play in the PGA Tour's Corales Puntacana Resort and Club Championship in Punta Cana, Dominican Republic from March 22–25. Romo missed the cut with scores of 77 and 82, dead last in the 132-man field after the second round. In July 2018, he won the American Century Championship, a celebrity tournament.

Romo signed as an undrafted free agent with the Cowboys in 2003. Beginning his career as a holder, Romo became the Cowboys' starting quarterback during the 2006 season. Serving as the team's primary starter from 2006 to 2015, he guided the Cowboys to four postseason appearances and was named to the Pro Bowl four times. Romo retired after the 2016 season, following a preseason back injury that caused him to lose his starting position to Dak Prescott. Upon retiring, he was hired by CBS Sports to become the lead color analyst for their NFL telecasts, teaming with Jim Nantz in the broadcast booth.

Romo did not initially receive an invitation to attend the 2003 NFL Combine, but received a late invitation to attend as an extra quarterback to throw passes to other prospects during drills. Despite intriguing some scouts, he went undrafted by any NFL team during the 2003 NFL Draft. Throughout the draft, Romo was assured by Sean Payton of the Cowboys' interest (Romo was also intensely pursued by Denver Broncos head coach Mike Shanahan), and shortly afterwards was signed as an undrafted rookie free agent by the Cowboys. Romo entered the 2003 training camp third on the Cowboys' depth chart behind Quincy Carter and Chad Hutchinson. In 2004, the Cowboys released Hutchinson and signed veteran quarterback Vinny Testaverde and traded a third-round draft pick to the Houston Texans for quarterback Drew Henson. Romo faced being cut from the roster until Carter was released following allegations of substance abuse. Throughout 2004 and 2005, Romo served as the holder for placekicks. After Vinny Testaverde's tenure in Dallas ended in 2005, the Cowboys signed veteran quarterback Drew Bledsoe, the team's eighth starting quarterback since 2000.

Romo aided the Cowboys in clinching a playoff spot, their second since Parcells became coach in 2003. He concluded the 2006 regular season with 220 completions on 337 pass attempts for 2,903 yards, 19 touchdowns, and 13 interceptions, with a passer rating of 95.1.

Romo earned OVC Player of the Week honors on October 14, 2002, after his eight-yard scramble run on the last play of the game led Eastern Illinois to a 25–24 win over Eastern Kentucky.

On December 19, 2002, Romo became the first player in Eastern Illinois and Ohio Valley Conference history to win the Walter Payton Award, given annually to the top Division I-AA football player. He finished his career holding school and conference records with 85 touchdown passes. He finished second in school and third in conference history with 8,212 passing yards and second in school history with 584 completions and 941 attempts. As a senior, he set school and conference records for completions with 258 in 407 attempts for 3,418 yards. This was second in conference and third in school history for a season. He threw for 34 touchdowns and scored one rushing touchdown. Romo's 3,149 yards in total offense as a senior ranked third in school and conference history. Along with the Walter Payton Award, Romo earned consensus All-America honors. In addition, he was selected All-Ohio Valley Conference and was named OVC Player of the Year for the third straight year.

Romo attended Eastern Illinois University in Charleston, Illinois, where he played for the NCAA Division I-AA Eastern Illinois Panthers football team and was a member of Sigma Pi. As a sophomore in 2000, he ranked second in Division I-AA in passing efficiency, completing 164-of-278 (59%) passes for 2,583 yards and 27 touchdowns. After the season, he was honored as an All-America honorable mention, an All-Ohio Valley Conference member, and the OVC Player of the Year. As a junior, he led Division I-AA in passing efficiency, completing 138-of-207 passes for 2,068 yards and 21 touchdowns.

Romo started as quarterback for the Burlington High School Demons beginning as a junior (1996 season). In the 1997 season, Romo and the Demons finished with a 3–6 record, though he earned several honors, including the All-Racine County football team and Wisconsin Football Coaches Association All-State first team honors. Romo also was a starter on the Burlington High School varsity basketball team and also played golf and tennis. Romo graduated from Burlington High School in 1998.

Antonio Ramiro Romo (born April 21, 1980) is an American football television analyst and former quarterback who played his entire 14-year career with the Dallas Cowboys of the National Football League (NFL). He played college football for Eastern Illinois University, where he won the Walter Payton Award in 2002 and led the Panthers to an Ohio Valley Conference championship in 2001.

Romo opened the season with a win over the New York Giants, passing for 263 yards and two touchdowns. He briefly left the game with a rib injury, but returned after halftime and finished the game. After Week 7, his 100th career start, Romo had thrown for 27,485 yards, the most by a quarterback in his first 100 starts since 1960.