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The Bears went 8–8 in 2019 and missed the playoffs. On January 16, 2020, Nagy hired John DeFilippo as quarterbacks coach and Ragone was promoted to pass game coordinator.

During the 2017 NFL Draft, the Bears selected quarterback Mitchell Trubisky with the 2nd overall pick. They also signed former Tampa Bay Buccaneers starting quarterback Mike Glennon in free agency. The Bears went 5–11 and missed the playoffs for the fourth consecutive season.

When Fox was fired after the 2017 season, Ragone was retained by new coach Matt Nagy; he was the lone offensive assistant from the Fox regime to stay with the Bears. The Bears went 12–4 in 2018, earning a winning season for the first time since 2012, and making the playoffs and winning the NFC North for the first time since 2010. They would go on to lose to the Philadelphia Eagles in the wild card round 16–15 with Trubisky setting numerous franchise passing records. Under his coaching, Trubisky would be selected to the Pro Bowl.

On January 22, 2016, he was named quarterbacks coach of the Chicago Bears under head coach John Fox. The Bears went 3–13 and missed the playoffs, the worst record for the franchise since the NFL moved to 16-game seasons in 1978. Although Ragone was tasked with coaching quarterback Jay Cutler, Cutler and the team struggled with injuries, forcing backups Brian Hoyer and Matt Barkley into action. The Bears also went 0–8 on the road for the first time in franchise history.

On February 27, 2015, he was hired as the offensive quality control coach for the Washington Redskins.

Ragone attended St. Ignatius High School and was a student and a letterman in football and basketball. In football, as a senior quarterback, he was an All-State first team honoree and led his team to the State Semi-Final game, losing 20–19 against Canton McKinley. Also as a senior, he was a starter on the basketball team that went on to be the State Runner-Up.

During his college career at the University of Louisville, he went 27–11 as a starting quarterback, including an 11–1 mark in 2001. Ragone finished his college years as Louisville's second all-time leading passer. He was a three-time All-American honorable mention and three-time Conference USA Offensive Player of the Year.

On January 18, 2013, Ragone was reassigned from wide receiver to quarterbacks coach, replacing Dowell Loggains who was promoted to offensive coordinator after the Titans fired Chris Palmer on November 26, 2012. The Titans went 7-9 and missed the playoffs for the fifth straight year. At the end of the season, head coach Mike Munchak was fired, leaving Ragone without a job.

During the 2012 NFL draft, the Titans selected wide receiver Kendall Wright with the 20th pick. Wright would go on to lead all NFL rookies with 64 receptions. The Titans went 6-10 in 2012, and missed the playoffs for the fourth straight year.

He was named wide receivers coach of the Tennessee Titans on February 22, 2011, following his head coach Chris Palmer who was named offensive coordinator on the 15th. During the 2011 season, the Titans went 9–7 and missed the playoffs for the third consecutive season. Under his coaching, wide receiver Nate Washington eclipsed 1,000 yards and recorded seven touchdowns.

On March 19, 2010, Ragone was named the wide receiver/quarterback coach for the Hartford Colonials of the United Football League. Under his coaching, quarterback Josh McCown was named Offensive Player of the Week on September 20, 2010. He would also lead the league in passer rating & touchdown passes.

In the fall of 2009, Ragone was inducted into the Saint Ignatius Athletic Hall of Fame.

Ragone was released by the Rams during training camp prior to the 2006 season. He then began a sports talk show on Louisville, Kentucky radio station WQKC.

He was selected in the third round of the 2003 NFL draft by the Houston Texans and started in two games behind David Carr. In 2005, Ragone was named NFL Europe's Offensive MVP, leading the Berlin Thunder to World Bowl XIII. Ragone was waived by the Texans and claimed by the Cincinnati Bengals in May 2006. In June 2006, the Bengals traded Ragone to the St. Louis Rams.

David Patrick Ragone (born October 3, 1979) is an American football coach and former player who is the pass game coordinator for the Chicago Bears of the National Football League (NFL). He played in the NFL and NFL Europe for four seasons. He played college football for the University of Louisville.