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In October 2019, Bryant stated that he was going to rehabilitate and train during the 2019 season. He said he did not plan on retiring and wanted to return to play football in 2019, but did not sign with a team.

The Cowboys released Bryant on April 13, 2018, after eight seasons with the team.

On November 7, 2018, nine weeks into the 2018 season, Bryant agreed to a one-year, $1.25 million deal with the New Orleans Saints.

Bryant started the 2017 season with two receptions for 43 yards in the 19–3 victory over the New York Giants on NBC Sunday Night Football. During a Week 9 28–17 victory over the Kansas City Chiefs, Bryant sprained his ankle, and was sidelined for the rest of the game.

On November 30, against the Washington Redskins, Bryant passed Bob Hayes for the Cowboys franchise record for receiving touchdowns. Overall, he played in all 16 games in the 2017 season and recorded 69 receptions for 838 yards and six touchdowns as the Cowboys finished with a 9–7 record and missed the playoffs.

Bryant started the 2016 season with a new starting quarterback in Dak Prescott as Tony Romo suffered a back injury in the preseason. After recording a single reception for eight yards in the season opening loss to the New York Giants, he had seven receptions for 102 yards in a Week 2 27–23 victory over the Washington Redskins. Bryant suffered a hairline fracture in his knee in Week 3 against the Chicago Bears, forcing him to miss extended time. He returned in Week 8 against the Philadelphia Eagles to finish the second half of the season, tallying 50 receptions for 796 yards and a team-high eight touchdowns in 13 games played. Bryant's best performance of the year came in the postseason against the Green Bay Packers in the Divisional Round, where he recorded nine receptions for 132 yards and two touchdowns in a 34–31 defeat. Bryant was named to the Pro Bowl for the third time in his career, replacing Julio Jones, who could not participate due to the Atlanta Falcons advancing to Super Bowl LI. He was ranked 60th by his fellow players on the NFL Top 100 Players of 2017.

On March 3, 2015, the Cowboys placed the nonexclusive franchise tag, worth $12.823 million, on Bryant. On July 15, 2015, Bryant and the Cowboys reached an agreement on a five-year, $70 million contract that included $45 million of guaranteed money and a $20 million signing bonus.

During Sunday Night Football against the New York Giants on September 13, 2015, Bryant left the game with a foot injury. An x-ray revealed a fracture in the foot that required surgery. Recovery time for Bryant's injury required 4–6 weeks. He returned in Week 8 against the Seattle Seahawks and struggled, recording two receptions for 12 yards in a 13–12 loss to the Seahawks in AT&T Stadium. Week 9 against the Philadelphia Eagles, Bryant caught his first touchdown of the season on a day where he totaled five catches for 104 yards in the 33–27 loss. Limited to nine games in the 2015 season, Bryant had 31 receptions for 401 receiving yards and three touchdowns. He was ranked 51st by his fellow players on the NFL Top 100 Players of 2016. On January 6, 2016, he underwent foot and ankle surgeries.

Bryant started all 16 games and finished the season with 93 catches and 13 touchdowns, both career highs, and 1,233 receiving yards. These ranked eighth in catches, 13th in yards, and third in touchdowns, respectively, among all receivers. Bryant went to his first Pro Bowl. He was ranked 25th by his fellow players on the NFL Top 100 Players of 2014.

Bryant was born on Galveston Island at The University of Texas Medical Branch, but eventually moved to Lufkin, Texas, where he attended Lufkin High School. While at Lufkin High School, he played high school football for the Panthers football team. As a junior, he caught 48 passes for 1,025 yards and 16 touchdowns. Bryant led Lufkin to a 14–1 record, including an appearance in the 5A Division II state semifinals, where they lost 46–28 to Todd Dodge's Southlake Carroll. In his senior year, Bryant had 53 receptions for 1,207 yards with 21 touchdowns, and was an All-State selection. Lufkin finished the season with an 11–1 record, after losing 38–25 to Round Rock in the area round of the playoffs. After the season, Bryant participated in the Offense-Defense All-American Bowl. He was named an All-American by Parade and SuperPrep.

On September 1, Bryant made his collegiate debut against Georgia and had one reception for seven yards in the 35–14 loss. On September 22, against Texas Tech, he had five receptions for 51 receiving yards and his first collegiate receiving touchdown, a five-yard reception from Zac Robinson, in the 49–45 victory. On October 20 against Kansas State, he had three receptions for 37 receiving yards and two receiving touchdowns in the 41–39 victory. On November 10, against Kansas, he set a school record for receiving yards in a game by a freshman with 155 in the 43–28 loss. In the 2007 Insight Bowl, he recorded nine receptions for 117 receiving yards and two receiving touchdowns in a 49–33 win against the Indiana Hoosiers. As a freshman in 2007, he finished second on the team with 43 receptions for 622 receiving yards and six receiving touchdowns in 12 games.

On September 6, against Houston, he had nine receptions for 236 receiving yards and three receiving touchdowns to go along with a punt return touchdown in the 56–37 victory. On September 27, against Troy, he had six receptions for 118 yards and three receiving touchdowns in the 55–24 victory. In the next game, against Texas A&M, he had 106 receiving yards, three receiving touchdowns, and a punt return touchdown in the 56–28 victory. On October 18, against Baylor, he had 11 receptions for 212 receiving yards and two receiving touchdowns in the 34–6 victory. On November 1, against Iowa State, he had nine receptions for 171 yards and four receiving touchdowns in the 59–17 victory. On November 29, against Oklahoma, he had six receptions for 91 receiving yards and two receiving touchdowns in the 61–41 loss. On December 30, against Oregon in the 2008 Holiday Bowl, he had 13 receptions for 167 yards and a receiving touchdown in the 42–31 loss. He finished the 2008 season with 87 receptions for 1,480 receiving yards and 19 receiving touchdowns, including two punt returns for touchdowns.

Bryant had four receptions for 85 yards in a 24–17 win against the New York Giants in the season opener. The next two games were average performances, totaling only 79 receiving yards on nine receptions and no touchdowns. Dallas lost the game in Week 2 against the Seattle Seahawks by a score of 27–7 and won in Week 3 against the Tampa Bay Buccaneers by a score of 16-10. In the Week 4, 34–18 loss to the Chicago Bears, Bryant had eight receptions for 105 yards. This marked the fourth straight game of the season without a touchdown, and no touchdowns on 21 catches for the season that point. After the Week 5 bye, Bryant caught his first two touchdowns of the season, while setting his career-high 13 receptions in a Week 6 loss to the Baltimore Ravens by a score of 31-29. With 32 seconds remaining in the game, Bryant caught a touchdown pass from quarterback Tony Romo to bring the score to 31–29. Following a failed two-point conversion, Dallas recovered an onside kick to give the offense one last opportunity to win the game. Kicker Dan Bailey attempted a 51-yard field goal, but it sailed wide left to end the game 31–29. Throughout September and October, Bryant was being criticized in the media for dropping balls, fumbles and running poor routes, but he started to live up to his potential in a Week 8 game against the New York Giants, when he registered 110 yards on only five catches, and almost came up with a last-minute hail mary touchdown, but it was reversed because his hand was ruled out of bounds. Against the Eagles, he amassed 87 yards on three catches, with one touchdown. This brought his Week 9 and 10 performances to 102 yards on four receptions and one touchdown. That Week 10 performance was the start of a breakout season, worthy of Pro Bowl consideration. In Week 11 against the Cleveland Browns, Bryant had 12 catches for a then-career-high 145 yards, breaking his previous personal best of 110 yards during Week 8 against the Giants. In Week 12, against the Washington Redskins, he head eight receptions for 145 receiving yards and two receiving touchdowns in the 38–31 loss. Against the New Orleans Saints in a Week 16 loss, he had the best game of his career to that point, with nine receptions for a career-high 224 yards, two touchdowns, and tying the franchise record for most consecutive games, with seven, with at least a touchdown reception, which is shared with Franklin Clarke (1961–1962), Bob Hayes (1965–1966), and Terrell Owens (2007). Dez's 224 receiving yards were the fourth most in franchise history at the time. In the last game of the season, Bryant had four receptions for 71 yards in the Week 17 loss to rival and eventual division champions, the Redskins. Since week 10 and the midway point of the 2012 season, Bryant accumulated 879 yards and 10 touchdowns on 50 receptions (17.6 yards/catch average).

Bryant started the 2013 season with four receptions for 22 yards in a Week 1 36–31 victory over the New York Giants. He had nine receptions for 141 receiving yards and a touchdown in a Week 2 loss to the Kansas City Chiefs. Over the course of the next two weeks, Bryant had ten receptions for 119 yards with three touchdowns, in a 31–7 win over the St. Louis Rams and a 30–21 loss to the San Diego Chargers. In a Week 5, 51–48 shootout loss to the Denver Broncos, Bryant had six receptions for 141 yards and two touchdowns. On October 20, he had eight receptions for 110 yards in a 17–3 win over the Philadelphia Eagles. In the next game, a 31–30 loss to the Detroit Lions, he had 72 receiving yards and two touchdowns. In a narrow Week 15 37–36 loss to the Green Bay Packers, Bryant finished with a season-high 11 catches for 153 receiving yards and one receiving touchdown.

Bryant caught five passes for 55 yards while the Cowboys were beaten at home in Week 1 by the San Francisco 49ers by a score of 28–17. However, over the next six weeks, the offense improved as they won six straight games and Bryant was dominant over the stretch, catching 41 passes for 535 yards and four touchdowns.

During Week 8 against the Washington Redskins, Tony Romo was injured and forced to miss a good portion of the game (he later returned to finish the game). As a result, the Cowboys' offense, with Brandon Weeden under center, struggled and Bryant's production decreased as a direct result. Romo missed the following week with an injured transverse process, and the Cowboys were beaten by the Arizona Cardinals by a score of 28–17. Bryant had five catches for 45 yards and two touchdowns during this stretch. Romo returned the following week against the Jacksonville Jaguars, and Bryant's production increased when he caught six passes for 158 yards and two touchdowns in the second quarter alone, making this the most productive quarter of his career. With Romo back for the remaining six games, Dallas began to dominate as Bryant compiled 32 catches for 527 yards and eight touchdowns. He was named NFC Offensive Player of the Week for Week 15. During this stretch, Dallas was 5–1 and finished with a record of 12–4, which tied for most wins in the NFL during the 2014 season. Bryant finished with 88 receptions for 1,320 yards and 16 touchdowns. It was his third consecutive season with double-digit touchdowns.

In the Divisional Round, the Cowboys lost to the Green Bay Packers 26–21. The game is noted for a controversial call that reversed a complete 31-yard pass to Bryant on fourth-and-2 from the Packers' 32. Although Bryant, covered by Sam Shields, caught the ball with both feet coming down in bounds, Bryant bobbled the ball as he stretched towards the 1-yard line. Referees initially ruled Bryant down at the 1-yard line, but overturned this call as an incomplete pass following a challenge from Packers' coach Mike McCarthy. Referee Gene Steratore explained the decision: "Although the receiver is possessing the football, he must maintain possession of that football throughout the entire process of the catch. In our judgment, he maintained possession, but continued to fall and never had another act common to the game. We deemed that by our judgment to be the full process of the catch, and at the time he lands and the ball hits the ground, it comes loose as it hits the ground, which would make that incomplete; although he repossesses it, it does contact the ground when he reaches, so the repossession is irrelevant because it was ruled an incomplete pass when we had the ball hit the ground." Bryant said after the game that he believed it was a catch without a doubt, and wanted to know why his catch was overturned. Dean Blandino, NFL vice president of officiating, also confirmed that the play was correctly reversed by tweeting "Bryant going to the ground. By rule he must hold onto it throughout entire process of contacting the ground. He didn't so it is incomplete." Later, during the following offseason, according to The Fort Worth Star-Telegram, Blandino met with the Cowboys stating "The message to the coaches and players – because we've gone out and visited with every staff – is if you're falling to the ground to make the catch, then you have to maintain the control when you land," Blandino said. "And if you reach or do anything with the football, that's not going to trump that requirement to maintain control." In the offseason, he was ranked 15th by his fellow players on the NFL Top 100 Players of 2015.

Bryant finished the 2012 season with 92 receptions for 1,382 yards and 12 touchdowns; these ranked 10th, sixth, and third, respectively, among all receivers. He suffered from several injuries throughout the second half of the season. He injured his finger in early December, opting to play through the injury for the duration of the season, saying that opponents would "have to break my leg to keep me out." He left in the fourth quarter of the final game of the season against the Redskins with a back injury. Head coach Jason Garrett stated after the game that Bryant "could barely walk", with the injury. He was ranked 35th by his fellow players on the NFL Top 100 Players of 2013.

On July 16, 2012, Bryant was arrested on a class A misdemeanor domestic violence charge for allegedly striking his biological mother, Angela Bryant. In March 2013, Bryant spoke at an event for Dallas Men Against Abuse. At the event, he stated, "I'm done with domestic abuse." On August 28, 2014, Bryant launched his official brand and apparel line, ThrowUpTheX. On June 22, 2016, Bryant was sued by Texas state senator Royce West for damaging a rented house in DeSoto, Texas. Damage to the rental house totaled over $60,000.

Bryant started the first game of the 2011 season against the New York Jets where he had three receptions for 71 yards and a touchdown in a 27–24 loss. Bryant missed the next game against the San Francisco 49ers due to injury, as the Cowboys won the game by a score of 27–24 in overtime. Bryant started his second game of the season against the division rival and previously undefeated Washington Redskins on a Monday Night Football game. Playing injured, Bryant managed four receptions for 63 yards in the 18–16 victory. In the fourth game of the season against the undefeated Detroit Lions, Bryant had three receptions for 37 yards, one rush for five yards, and two receiving touchdowns in his team's 34–30 loss. His two-touchdown game marked just the second time in his career with multiple touchdowns in one game. In Week 7, the Dallas Cowboys went up against the St. Louis Rams at Cowboys Stadium. In the contest, Bryant had the most productive game of his season thus far, hauling in five receptions for 90 yards and a touchdown, helping his team to a 34–7 win. His receptions that game ranked fourth-most receptions in a game and his 90 yards were his second-most yards in a game for his career. His yardage output of the game also ranked as the most yards in a single game for his 2011 season. Bryant was not officially given the start for the game. Bryant's best game of the season was overshadowed by rookie teammate DeMarco Murray's record-breaking day. The following week, in a 23–13 victory over the Seattle Seahawks, Bryant recorded four receptions for 76 yards on nine targets. Bryant fumbled and lost the fumble, both for the first time in his career, as he was tackled near the opponent's 1-yard line. From Week 13 to Week 15, he scored a receiving touchdown in all three games. Bryant finished the season with 63 receptions for 928 yards and nine touchdowns.

Bryant had a troubled upbringing, born to a 15-year-old mother who was arrested for dealing crack cocaine when Bryant was eight years old. He went on to live in eight different homes while attending Lufkin High School. Bryant has two sons, Zayne and Dez Jr. Bryant was sued in March 2011 for $861,350 for legal fees and the cost of jewelry, which he acquired on credit while a student athlete. The case was settled before court proceedings for between $400,000 and $500,000.

Bryant was signed by the Cowboys to a contract very similar to that of Vikings' wide receiver Percy Harvin (five years, $12.05 million, roughly $8.4 million guaranteed) on July 22, 2010. On July 23, 2010, it was announced that Bryant would wear the #88 jersey, the same as Hall of Famer Michael Irvin, and Cowboys legend Drew Pearson.

On September 12, Bryant made his NFL debut against the Washington Redskins and had eight receptions for 56 yards. In the next game, he had a punt return touchdown in the 27–20 loss to the Chicago Bears. On October 17, Bryant caught his first NFL touchdown catch, on a 31-yard pass from Tony Romo. The Cowboys ended up losing that game 24–21. In a Monday Night Football game against the New York Giants, at Cowboys Stadium on October 25, 2010, Bryant caught four passes for 54 yards, two of them for touchdowns, and also returned a punt 93 yards for a touchdown, making the longest Cowboys' punt return since Dennis Morgan's 98-yard return during the 1974 NFL season. On November 15, 2010, Bryant caught three passes for 104 yards and one touchdown, to become the first Cowboys rookie with a 100+ yard game since Antonio Bryant. During the fourth quarter of the Cowboys' 38–35 victory over the Indianapolis Colts, Bryant went down with a fractured ankle. Indianapolis' Kavell Conner held onto Bryant's leg while tackling him on a kickoff return, and the Cowboys immediately took Bryant to the locker room. He was placed on the injured reserve list and had surgery on the fractured ankle. He left the game with one catch for 14 yards and a 35.7-yard average on three kickoff returns.

Bryant finished his rookie season with 45 receptions for 561 yards and six touchdowns. He was named to the NFL All-Rookie Team for the 2010 season.

Bryant was ruled ineligible for the rest of the 2009 season on October 7 for violating an NCAA bylaw. He failed to fully disclose his interaction with Deion Sanders, a former NFL player, to the NCAA. He was considered the best wide receiver in 2009 and a possible Heisman Trophy contender before the suspension. In three games, he finished with 323 receiving yards, four receiving touchdowns, and a punt return touchdown.

On November 5, 2009, Bryant announced his intentions to enter the 2010 NFL Draft. He was widely believed to be the best wide receiver available and to be targeted by the Denver Broncos, who traded their Pro Bowl receiver Brandon Marshall to the Miami Dolphins prior to the draft, with the 11th overall pick. If he slipped by the Broncos, Bryant was projected to fall no lower than the 27th pick to the Dallas Cowboys. After dropping because of character concerns, the Cowboys traded up with the New England Patriots, moving from the 27th to the 24th position to select Bryant. For the move, the team sent a third-round draft choice, which was the 90th overall pick, while receiving the Patriots' fourth-round draft choice, which was the 119th overall pick.

The Cowboys made the playoffs for the first time since 2009 and Bryant played in his first playoff game, against the Detroit Lions. In a defensive struggle, Bryant saw double coverage for most of the night and was largely unproductive. However, after some second-half adjustments by the Cowboys, the Dallas offense took advantage of the added attention to Bryant and began to move the ball frequently through the air, targeting Bryant's counterparts in the receiving corps and the Cowboys won 24–20 after being down 20–7 late in the third quarter. The game was not without controversy; as the Lions were ahead on the scoreboard, 20–17, facing a third-and-1, quarterback Matthew Stafford threw a pass to tight end Brandon Pettigrew, who was seemingly interfered with by Cowboys linebacker Anthony Hitchens, and the referees threw a flag and announced a pass interference. After about a minute, the referees gathered their flags and declared no foul on the play, which resulted in a fourth-and-1. After an attempt to draw Dallas offsides, Detroit punted the ball back to the Cowboys and Dallas drove 59 yards and scored the game-winning touchdown.

Regarded as a four-star recruit by Rivals.com, Bryant was listed as the no. 9 wide receiver prospect in the class of 2007, and the second from Texas behind only Terrence Toliver. Recruited by numerous major programs, including most Big 12 schools, Bryant took official visits to Texas A&M, Oklahoma State, and Texas Tech, before committing to the Cowboys. He was just the fourth Parade All-American to sign with Oklahoma State since 1985.

Bryant attended Oklahoma State University from 2007 to 2009 and was a member of the Oklahoma State Cowboys football team coached by Mike Gundy.

Desmond Demond Bryant (born November 4, 1988) is a former American football wide receiver. He played college football at Oklahoma State, where he earned All-American honors in 2008. He was drafted by the Dallas Cowboys in the first round of the 2010 NFL Draft, earned three Pro Bowl berths, and was a First-team All-Pro player in 2014.