Jay Cutler

At 40 years old, Jay Cutler has this physical status:

Jay Christopher Cutler (born April 29, 1983) is a former American football quarterback who played in the National Football League for 12 seasons, primarily with the Chicago Bears.

He played college football at Vanderbilt and was drafted by the Denver Broncos in the first round of the 2006 NFL Draft, for whom he played for three seasons.

In 2009, he was traded to the Bears, where he played for eight seasons.

After being released by Chicago in 2017, Cutler initially retired to become a sportscaster for NFL on Fox's television broadcasts, but returned for one more season with the Miami Dolphins when quarterback Ryan Tannehill suffered a season-ending injury.

He retired a second time following the 2017 season.

Early years

Cutler was born in Santa Claus, Indiana in 1983. Cutler attended Heritage Hills High School in Lincoln City, Indiana. He started three years at quarterback for the Patriots football team, amassing a combined 26–1 record in his junior and senior years, including a perfect 15–0 during his senior year. Cutler and his team outscored opponents 746–85, including a 90–0 shutout at Pike Central. During his senior year, Cutler connected on 122 of 202 passes (60.4%) for 2,252 yards with 31 touchdowns, while rushing 65 times for 493 yards with 11 touchdowns. He also started at safety for three years, intercepting nine passes as a senior, 12th overall in the state. His team's perfect record during his senior year included the school's first 3A state championship, where Heritage Hills beat Zionsville in overtime, 27–24. The most notable play of the game occurred when Cutler lateraled the ball to the halfback, Cole Seifrig, who then passed it to Cutler who ran it into the end zone. Cutler also played strong safety in the state championship and made 19 tackles.

Cutler was named a first-team All-State selection by the Associated Press as a senior. In addition to playing football in high school, he was a first-team all-state selection in basketball, scoring 1,131 points; he co-holds the school record for FGs made (16) in a game and garnered honorable mention all-state accolades as a shortstop in baseball.

Cutler grew up as a Chicago Bears fan during his youth in Indiana.

Personal life

Cutler began dating Kristin Cavallari in September 2010 and became engaged to her in April 2011. They called off the engagement in July 2011, but subsequently confirmed their reconciliation that November. Cutler and Cavallari married on June 7, 2013, in Nashville, Tennessee. They have two sons and one daughter. Despite the birth of his first son coming the day before the Bears played their preseason opener against the Denver Broncos, Cutler dressed for the game, though he did not play.

In April 2020, the couple announced that they are getting a divorce, with Cavallari saying the split came as a result of the two simply "growing apart." As of May 2021, the couple had not finalized their divorce due to financial issues. In June 2022, it was reported that their settlement had been finalized and the couple were officially divorced.

Cutler does volunteer work for young people with developmental disabilities through Vanderbilt's "Best Buddies" program.

During the 2007 offseason, Cutler started the Jay Cutler Foundation, which partnered with Mile High United Way's Youth Success Initiative to help at-risk youth overcome obstacles and graduate from high school.

On May 1, 2008, Cutler announced that he was diagnosed with type 1 diabetes and needs daily insulin shots. He is responding well with the insulin treatments.

Cutler works with Dedicated to Diabetes, which is a Denver-based organization that aims to improve public knowledge about diabetes.

For the 2009 season, Cutler teamed up with Eli Lilly and Company in a campaign called "Touchdowns For Diabetes". For every touchdown pass Cutler threw during the 2009 season, Lilly sent a child to diabetes camp by donating $1,000 to the ADA's "Camp Scholarship" fund—roughly the cost of providing tuition for one child to attend a week of diabetes camp. For every pass Cutler completed in 2009, Lilly donated $100 to the ADA Camp Scholarship fund to allow even more kids the chance to attend camp the following summer.

In 2012, Cutler visited Perspectives Charter School in Chicago, and talked about diabetes awareness.

Source

College career

Cutler attended Vanderbilt University in Nashville, Tennessee. He redshirted in his 2001 freshman year and then started all 45 games for the Vanderbilt Commodores football team, the most ever played by a quarterback in college. Due to injury, he did not miss a game in college. During his tenure, the Commodores were 11–35, with one of them going 5–27 against the SEC. Cutler set the school record for touchdowns and rushing yards as a freshman and rushed for more yards than any other Southeastern Conference quarterback this year. He was named in the Associated Press as a first-team freshman All-SEC pick. Cutler's highest completion rate in 2004 was 61.0 percent, a school record, when he was throwing for 1,844 yards with 10 touchdowns and a career-low five interceptions.

Cutler's last year of play at Vanderbilt in 2005 was his most fruitful. He went for 373 of 462 passes (59.1%) for 3,073 yards, 21 touchdowns, and nine interceptions as the first Commodore to win the SEC Offensive Player of the Year (coaches and media) since 1967. Cutler became the second Commodore to throw for more than 3,000 yards in a season, with his 273 completions and 21 touchdowns ranked second on the school's single-season list. He led the Commodores to victories over Wake Forest, Arkansas, Ole Miss, Richmond, and Tennessee. The Commodores also scored their second most points ever (42) on the Florida Gators at their new home field in Ben Hill Griffin Stadium. Vanderbilt nearly shocked the 13th-ranked Gators before falling 49-42 in the second overtime after a contentious extra celebration called off the Commodores from going for 2 at the end of regulation. "If this guy can take a slew of future doctors and attorneys and have them competing against the Florida Gators, this guy is a stud," Broncos safety John Lynch said, based on Cutler's college career.

Cutler's career began when he led Vanderbilt past Tennessee 28–24, their first over the Volunteers since 1982 (the year before Cutler was born), and the first in Knoxville since 1975. Cutler finished with three touchdowns and 315 yards, becoming the first quarterback in school history to record four straight 300-yard passing performances. Earl Bennett's last game in college was the game-winning (and streak-ending) touchdown pass over Tennessee to teammate Earl Bennett. Cutler, a finalist for the Johnny Unitas Golden Arm Award (nation's top senior quarterback), was a first-team All-SEC pick chosen by the league's administrators and led the league with a school record of 3,288 yards of total offense.

Cutler, a three-year captain and four-year starter, set school records for total offense (9,953), passing yards (8,697), pass attempts (1,242), and combined touchdowns (76).

Cutler earned a bachelor's degree in human and organizational growth in 2005 from Vanderbilt.

Vanderbilt University's school careers: The school's record:

Professional career

Several experts had ranked Cutler as the third best quarterback prospect in the 2006 NFL Draft, after Matt Leinart of USC and Vince Young of Texas. Chris Mortensen and Ron Jaworski rated him as the best quarterback in the draft, and several scouts thought he had better arm strength than Young and Leinart, even though he was compared to Brett Favre for his gunlinger attitude. Cutler made a 225-pound bench press run in 4.77 seconds at the 2006 NFL Scouting Combine (more than some linemen).

The Denver Broncos' 1st and 3rd round picks were selected, giving the 11th pick of the draft from the 11th pick of the first round. Many believed Cutler was chosen by the Broncos due to his lackluster results in Jake Plummer's AFC Championship Game last season. "We had no warning," Cutler said after being picked by Denver. I think I knew about 15 seconds before everyone else did." Cutler, as most predicted, was the third quarterback chosen after Young (3rd overall) and Leinart (10th). He is Vanderbilt's third first-round pick, followed by Will Wolford and Bill Wade. Cutler agreed to a six-year $48 million contract, which included $11 million in bonuses, on July 27, 2006.

Cutler was promoted from third to second on the Broncos' quarterback depth chart after a solid training camp in 2006, ahead of Bradlee Van Pelt. In the preseason, he had more yards passing than any other rookie.

Despite a 7–4 record, head coach Mike Shanahan officially announced Cutler will replace Jake Plummer as the starting quarterback on November 27, because, "I think he gives us the best chance to win right now." The controversial decision brought weeks of rumors and rumors about Cutler's impending promotion to a starting position.

Cutler completed his first snap in the second quarter on December 3 (Week 13), and after some initial jitters (0-3 with sack and fumble), he scored his first touchdown to tight end Stephen Alexander in the second quarter. He threw a spectacular 71-yard touchdown to fellow rookie Brandon Marshall in the fourth quarter to tie the game 20-20. It was one of the longest touchdown passes for a rookie in NFL history, as well as the second-longest pass play between two rookies in Broncos history. In the loss, he had two interceptions and three sacks.

Cutler tied tight end Tony Scheffler for two touchdowns in 48 seconds on December 10, the first time in league history that two rookies had two scoring passes.

Cutler's first victory came in his third appearance against the Arizona Cardinals on December 17, which was a 37-20 road victory. He ended the game 21-of-31 with 261 yards, two touchdowns, an interceptor, and a QB rating of 102. On the Broncos' third play of the season, one touchdown passed 65 yards in the air and was recorded as a 54-yard touchdown to Javon Walker. "You saw what he could do today," Shanahan told the world. It doesn't take a genius out of a genius to discover that this guy is calm, can make all the throws, and has a lot of confidence."

In his fourth season as coach, Cutler led the Broncos to a victory over the Cincinnati Bengals on Christmas Eve. He went 12-of-23 for 179 yards, two touchdowns, and one interception. In the third quarter, he led the Broncos on a 99-yard touchdown run that culminated in a Mike Bell two-yard touchdown pass. Cutler became the first rookie QB in NFL history to throw for at least two touchdowns in each of his first four games played, as a result of the two passing touchdowns in the game against the Bengals. In each of his first four starts, he became the second rookie in league history (fifth player overall) to have at least two touchdown passes.

In the last game of the season, the Broncos' hopes to clinch a playoff spot fell short when they fell 26–23 in overtime to the San Francisco 49ers. The Broncos' loss took them to a 9-7 overall record and a 4–4 at home. Despite suffering a concussion in the first half, Cutler finished 21 of 32 for 230 yards and a touchdown, and led Denver on a game-tying touchdown drive in the closing minutes of regulation to force overtime.

Cutler finished 2–3 for 1,001 yards, nine touchdowns, and five interceptions, his highest passer rating of 88.5 in five games played on the season. With at least 125 passing attempts, he had the second-highest touchdown percentage (6.6) and third-highest TD-to-INT ratio (1.8%) among NFL rookies since 1970.

Cutler's first full season as the Denver Broncos' starting quarterback. Cutler led Denver to a comeback victory over the Buffalo Bills in the first game of the season, culminating in a Jason Elam 42-yard field goal as time expired. Cutler's pass attempts (39), completions (23), and yards (304) for the game were all record-breaking highs at the time. In the home opener against the Oakland Raiders, he led Denver to their second straight victory in the home opener. Cutler completed the game 78 yards in 15 plays for the game-tying field goal with 2:18 remaining, despite being late in regulation. Elam's game went into overtime, where he engineered a 52-yard drive that resulted in another game-winning field goal. Cutler had a touchdown pass during the game, making him the first Broncos passer to start his Broncos career with at least one touchdown pass in his first seven appearances. The streak spanned nine games through losses to Jacksonville and Indianapolis (which featured his first career rushing touchdown), but the San Diego Chargers' 41–3 home loss in the fourth game of the season.

The 2-3 Broncos defeated the Pittsburgh Steelers 4–28 on last-second Elam field goals after the bye week in Week 6. Cutler's QB rating was 106.7 percent and career highs of 759 passes completed, three touchdowns, 41 passing yards, and a long run of 31 yards, earning NBC Sunday Night Football's Horse Trailer Player of the Game (with Elam). Cutler's 12th game against the Green Bay Packers, in which he drove 89-yards for a game-tying field goal in the last 2:27 of regulation, before losing in overtime, 19–13 on Green Bay's first game from scrimmage. Cutler had only four attempts against the Detroit Lions in week 8 before going home due to a leg injury; backup Patrick Ramsey floundered in a 44-7 loss. Cutler won by 27–11 at Kansas City last week, and he returned the next week.

In Week 10, the 4-5 Broncos faced the Tennessee Titans (and fellow 2006 draftee Vince Young for the first time) in a MNF game. In a 34–20 victory, Cutler posted his career-second-best 137.0 passer rating. He was the first Broncos quarterback to throw two 40+ yards in a game (of the team's franchise-record four 40+ yard touchdowns on the night), and the 5–5 Broncos tied San Diego in a tie in the AFC West, with Elway throwing two 40+ yards in a game. The Broncos won just one of the next five games, defeating the Chiefs 41–7. Cutler had four touchdowns and a then-career-best rating of 141.0 in the game. But the Broncos lost 23-3 to San Diego, despite a good spot in between two sets of losses; in the four games, Cutler had five interceptions, had 12 sacks, twice had a rating under 50.0, and twice lost the Broncos from the playoffs. With a 22-19 overtime victory over Minnesota, Cutler tied a 7–9 record, eliminating them as well.

Denver missed the playoffs for the second year in a row. Cutler played in all 16 games, totaling 297-of-467 passes (63.6%) for 3,497 yards, 20 touchdowns, and 14 interceptions. He was the NFL's 12th-ranked passer (88.1) and had the tenth-most passing yards (3,497). In addition, Cutler was the league's ninth-best third-down passer, with a 92.1 passer rating (93-of-125 for 901 yards, eight touchdowns, and three interceptions). It was the seventh most passing yards in Broncos history and the third highest completion percentage. Cutler, as his predecessor Plummer, demonstrated flexibility by running 44 rushes for 205 yards (4.7 yards per carry) and a touchdown on the season.

Several analysts believed Cutler would be the young quarterback with the most promise to succeed in late 2007, along the lines of Peyton Manning and Tom Brady. For the 2008 season, Cutler, Brandon Marshall, and Tony Scheffler met in Atlanta together to train and work on timing.

Cutler and tight end Daniel Graham were voted offensive captains by Broncos teammates before the 2008 regular season began.

With a 41-14 victory over Oakland on Monday Night Football, Cutler began the season. Cutler and the Broncos beat the San Diego Chargers 39-38 in Denver, 16-of-24 passes for 300 yards and two touchdowns. Cutler went 36-of-50, with 350 yards passing and a career-best-tying four touchdowns, including one to Eddie Royal on 4th and Goal with 0:24 left, and a game-winning two-point conversion to Royal followed. This happened on a play after Cutler's fumbled, but the Broncos returned the ball back after an inadvertent whistle by referee Ed Hochuli before the Chargers recovered. Cutler won 34-32 over New Orleans in Week 3, who had 264 yards and two touchdowns. For the first time in the Broncos' first loss, 33-19 at Kansas City, Cutler threw two interceptions for the first time. Despite this, he came in second in completions (102), passing yards (1,275), and attempts (157), and fifth in overall percentage (65.0%), placing second in AFC Offensive Player of the Month (96.06) for the first time in his career (96.06), and fifth in finishing percentage (65.0%).

With 227 yards, one touchdown, and no interceptions, the Broncos edged Tampa Bay 16-13. The Broncos were 4–1 and the best AFC West in AFC West. Cutler passed for 192 yards, two touchdowns, and one interception after a 24-17 loss to the Jacksonville Jaguars. Cutler's index finger was stabbed in the first play of a 41-7 loss at New England, and he finished the game with 168 yards and two interceptions. The Broncos lost their third straight defeat to Miami, 26-17, behind Cutler's 24-of-46 passing for 307 yards, two touchdowns, and season-high three interceptions. Cutler had all seven of the Broncos touchdowns on the 1-4 skid.

The Broncos were defeated 23-20 at Cleveland in game 9, but in the 4th quarter, Cutler threw a career-long 93-yard touchdown to Eddie Royal, and Brandon Marshall led to a touchdown stop, but the game-winners were down to Brandon Marshall with 1:14 remaining. Cutler's game was 24-of-42, with four47 yards (career-high), three touchdowns, and one interception, and he was named AFC Offensive Player of the Week for the first time in his career. For a 24-20 victory over Atlanta, Cutler threw another late 4th quarter touchdown to Daniel Graham in the fourth quarter.

In a 31-10 loss to Oakland, Cutler's streak of games with a touchdown ended at 11 after he went 16-of-37 for 204 yards and an interception. He did, however, reach 3,000 yards on the season, tying John Elway for the first time in 11 games. Cutler went 27-of-43 with 357 yards, two touchdowns, and one interception in a windy game 12 at the New York Jets. With four games remaining, the 7-5 Broncos had a 3-game road win streak, 3 game home loss streak, and a three-game lead on San Diego.

In a 24–17 victory over the Chiefs, Cutler began with a season high 80% of his 40 passes for 286 yards, two touchdowns, and one interception. For Cutler's fourth rally of the season, the win came thanks to a 95-yard field push and a go-ahead touchdown pass to Brandon Marshall. In a 20-30 loss at Carolina, Cutler was just 21-of-33 with 172 yards, one touchdown, and one interception, and there were no passing touchdowns and one interceptor in a 30–23 loss to Buffalo, despite 359 yards and two interceptions. The San Diego Chargers defeated the San Diego Chargers in a season finale that was decided on who takes the game. Cutler went 33-of-49 for 316 yards, one touchdown, and two interceptions, but it wasn't enough to stop the Chargers' seven touchdowns, and Denver lost 52-21, failing to make the playoffs for the third straight season.

Cutler finished the season with career-bests in passing completions (384), passing yards (616), passing yards (426), touchdowns (376), passing attempts (18), and running touchdowns (2). His passing yards, completions, and attempts were all single-season franchise records for the Broncos at the time. He also played the most 300-yard passing games (8 in team history). Cutler finished third in completions (first in the AFC), second in passing attempts (first in the AFC), third in passing yards (first in the AFC), and seventh in passing touchdowns (third in the AFC). He was named as the FedEx Air Player of the Week for his week of Weeks 10, 13, and 14. In the 2009 Pro Bowl, he came in third place in fan voting for AFC quarterbacks, and he was officially selected as a reserve. Peyton Manning, Nick Mangold, and Kris Dielman threw him into a pool before the game in Hawaii, ruining his blood sugar monitor. Cutler was unhurried in the case, and a replacement one was discovered in a drug store.

In the 2009 NFL Draft pick for quarterback Kyle Orton, the Bears' first- and third-round picks in 2009, he was traded with the Broncos' fifth-round pick in the Chicago Bears' fifth-round pick and first-round pick in the 2010 NFL Draft, along with the Bears' first-round pick and first-round pick in the 2010 NFL Draft. Cutler and the Bears came to an agreement on a two-year contract extension, worth $30 million, running through 2013.

During the Chicago Bears' mercurial season, Cutler was the object of most praise and critique. He started the season with 4 INTs in a loss to Green Bay, followed by seven touchdowns to one interception in three straight victories with a 100+ QB Rating. Cutler's 11 touchdowns versus NFL-leading 20 interceptions were missing eight of the next ten games. This included a Game 9 loss to San Francisco, where Cutler threw a career-high five interceptions and no touchdowns, as well as a Game 14 loss in Baltimore, where Cutler had career-worsts of 94 yards and a passer rating of 7.9. In Game 15 against Brett Favre's division rival Vikings, Cutler changed direction, throwing four touchdowns, including a go-ahead late in the 4th quarter and a 31-yard game-winner in overtime. For his play against the Vikings, he was named Offensive Player of the Week. He then won by over Detroit with another four-touchdown outing and another victory. Cutler ended the season with 27 touchdowns, championship-leading 26 interceptions, 3,666 yards passing, and a career-best passer rating of 76.8.

Mike Martz (known for assisting with the production of the St. Louis Rams' "Greatest Show on Turf") as offensive coordinator. Although Martz was critical of Cutler as an analyst, both analyst and analyst alike expressed apprehension about working together.

Cutler led the Bears to a 3–0 start, throwing six touchdowns and just two interceptions. However, Cutler was sacked nine times in the first half against the New York Giants in week 4, leaving him out for the remainder of the game and another with a concussion. In a loss to Washington that left the Bears 4–3 bye week, he returned to six sacks in a loss to Seattle and four interceptions.

Martz retooled the offensive line and demonstrated more dedication to the running game, allowing Cutler to finish the next three games with only six sacks total. In a victory over the 7–3 Eagles (winning NFC Player of the Week) and an 80 percent completion rate in a victory over Detroit, he won three touchdowns followed by then-career-bests of four touchdowns and an 86.2 rating. Cutler won back-to-back games with three touchdowns, one interception, and 100+ ratings in each, after losing to Green Bay in the season finale. The Bears earned an 11–5 record, an NFC North championship, and a first-round bye. Despite being fired in the league's highest 52 sacks, Cutler finished the season with 3,274 passing yards, 23 interceptions, 232 rushing yards, and four comeback victories.

In Cutler's playoff debut against the Seattle Seahawks, he had 274 passing yards, two passing touchdowns, 43 yards, and two rushing touchdowns, making him the second quarterback in NFL history since Otto Graham in 1954 and 1955 to pass two touchdown passes and two touchdown runs in a playoff game.

Cutler completed 6-of-14 passes for 80 yards and an interceptor before being sidelined early in the third quarter of a 21–14 loss to Green Bay due to a knee injury. The Bears did not announce Cutler's illness right away, allowing speculation to flourish. Cutler was being chastised seconds after the crash by Maurice Jones-Drew, Darnell Dockett, Deion Sanders, and Mark Schlereth, in possibly the NFL's first player-on-player social media assault. Lovie Smith, the Bears' coach, later admitted that he, not Cutler, made the decision after consulting the medical and training staff. Cutler's MCL had sprained his MCL the next day, according to an MRI. Troy Aikman, a Hall of Fame quarterback, said that the widespread reaction displayed hostility against Cutler's long-term polarizing attitude. Cutler was defended by Bears teammates, and his critics became the object of abuse from other players, including Packers Aaron Rodgers ("disrespective"), LeRoy Butler ("stupid"), and B. J. Raji ("pretty wrong and a lot of it has to do with envy").

Throughout 2011, offensive coordinator Mike Martz was often chastised for aggressive play-calling in a pass-good offense, resulting in unnecessary wear on a quarterback returning from injury. Cutler started the season off with 312 passing yards, two touchdowns, and one interception in the 30–12 victory. Cutler was sacked 6 times and kicked in the throat during Week 2 against the New Orleans Saints. Cutler was caught on camera asking a player to play on the sidelines and then "tell him I said fuck him!" during week 6. Despite all of these incidents, Cutler had a QB rating of 85.7 (11th in the league) by Week 10, and the Bears were 6–3. Cutler, on the other hand, thrashed San Diego's Antoine Cason after an interception on November 20. He was on the winning streak on the final drive, but the injury required season-ending surgery. The Bears lost six of their remaining seven games, including backups Caleb Hanie and Josh McCown, and missed the playoffs. Cutler had 2,319 passing yards, 13 touchdowns, and seven interceptions in his short 2011 season.

Before the season, the Bears cut Martz with Mike Tice, hired Cutler's former coach Jeremy Bates from the Broncos, and signed wide receiver Brandon Marshall from the Miami Dolphins. Unlike Martz, Tice allowed Cutler to call audibles at a time of scrimmage.

Cutler began his season by throwing an interceptions return for a touchdown by Colts' Jerrell Freeman. He improved from a passer rating of 4.9 on the first quarter. In a 41-21 victory, the game was 21-of-35 for 333 yards, two touchdowns, and a 98.9 passer rating. Cutler was shot seven times and threw four interceptions against Green Bay in Week 2, yelling at his porous offensive line and bumping left tackle J'Marcus Webb to his 28.2 passer rating in a 23-10 loss. In the next three games, the line responded by surrendering just five sacks, two touchdowns, no interceptions, and the second-best passer rating of his career (140.1). Cutler had three touchdowns and no interceptions in a 53-20 victory over Tennessee, bringing the Bears to 7–1 on the season, and Cutler's personal record in games with a 100+ QB rating to 25-0.

Cutler was the third NFL quarterback out with a concussion against the Houston Texans in Week 10. Jason Campbell, his replacement, was forced to miss the game and the following one. Cutler was back for a Week 12 victory over the Minnesota Vikings. Despite a 119.6 passer rating against the Seattle Seahawks in week 13, the Bears lost in overtime, followed by two close losses to Minnesota and Green Bay. Cutler closed the season with two good results against the Cardinals and Lions in straight victories. Despite a 10–6 record, the Bears missed the playoffs.

Cutler ended the season in the top 5 for times sacked, but he did place first in fourth-quarter passer rating with 114.7. He was also the Bears all-time team leader in passer rating (81.9) and completions (1,034), second in yards (12,292), touchdowns (82), and completion percentage (56%), in just four seasons (81.9) and completion (4,034). Brandon Marshall's reunion produced franchise records of 118 receptions for 1,508 yards, as well as the 7th-year receiver's first All-Pro pick.

Marc Trestman's new head coach created a winning tactic to shield his quarterback, but Cutler was suspended just nine times in the first six games compared to 23, 19, and 19 in the previous three seasons. Cutler's first game since 2009 was a 90+ passer rating in three games in a row. In each of those victories, he threw touchdowns in the 4th quarter, including game-winners against Cincinnati and Minnesota's week 2 in week 1. In a week 4 loss to Detroit, he threw three interceptions. Cutler was fired three times and fumbled in the first 16 minutes of the game, but he recovered for 358 yards, two touchdowns, and a season-high 128.1 passer rating in defeat in week five. In a Week 6 victory over the New York Giants, he threw 2 touchdowns. He had a career-best 95.2 passer rating, five multiple touchdown games, and a franchise-record 1,630 passing yards in the first six games.

Cutler tore a groin muscle against the Washington Redskins the next week, his 100th appearance on the team, beating Jim Harbaugh's franchise record for most times fired. Josh McCown was solid in recovery, barely missing the Redskins game in a 45–41 shootout, and after losing bye-week tossing two touchdowns in a 27–21 victory at Green Bay, he was a hero. Cutler was able to return early in the week ten games against Detroit, where he had 250 yards, one touchdown, and one interceptor before being kicked out of the game by Stephen Tulloch in the second quarter. McCown rushed for a touchdown in 90 seconds, but the Bears lost 21–19.

Cutler missed the next four games due to his injury, and McCown played well in his absence, contributing to some controversies when Cutler was reinstated as the starting QB in Week 15. In the first half against the Cleveland Browns, Cutler threw two interceptions, one returned for a touchdown but the other ended with a 102.2 passer rating and three touchdowns. Cutler had 14,687 career passing yards for the Bears, one more than Sid Luckman's franchise record. At home against Green Bay, the season finale was a winner-takes-the-division matchup. Despite Cutler's 15-of-24 passing for 226 yards, two touchdowns, and one interception for a 103.8 passer rating, the Bears lost 33–28 on a last-minute Hail Mary, missing the playoffs with an 8–8 record. Cutler finished the season with 224 of 355 passes for 2,621 yards, 19 touchdowns, 12 interceptions, and a career-best 89.2 passer rating.

Cutler agreed to a seven-year contract on January 2, 2014, extending his contract with the Bears through the 2020 NFL season.

In Trestman's second year as head coach, Cutler and the Bears struggled to a 5-11 record. In which Cutler threw two touchdowns and interceptions for 349 yards, the Bears opened the season on an overtime loss to the Buffalo Bills. To beat the San Francisco 49ers, the team overcame a 17-point deficit behind Cutler's four touchdown passes. He led the Bears to a 27–19 victory over the New York Jets next week, totaling 225 passing yards, two touchdowns, and no interceptions.

In two weeks, Cutler threw two touchdowns and two interceptions, as well as two interceptions. Cutler defeated Atlanta 27-13 in week 6 for a career-high 381 passing yards. In a loss to Miami, Cutler scored only 190 yards before throwing three touchdowns before losing by 51–23 to the New England Patriots and throwing two interceptions in an even worse 55–14 loss to the Packers. Former Bears linebacker Brian Urlacher said Phil Emery shouldn't have fired Cutler because he shouldn't have resigned him. "He is one of the top guys in the NFL in terms of financial terms..." He hasn't delivered like an elite quarterback, so he hasn't developed like an elite quarterback."

Cutler and the Bears won two straight games. Against the Vikings, he threw three touchdowns, two interceptions, and 330 yards, as well as one passing touchdown against Tampa Bay. That will be the season's last victory. Cutler led off two scoring touchdowns in a Thanksgiving Day game against Detroit, but the Bears struggled for the remainder of the game en route to 34-17 defeat. He had two touchdowns, two interceptions, and 280 yards in the game. The Bears suffered their eighth loss of the season to the Dallas Cowboys, in which Cutler threw 341 yards, two touchdowns, and one interception, effectively excluding the Bears from the playoffs. In a press conference, offensive coordinator Aaron Kromer partially blamed Cutler's audibles and impromptu play for the poor results, but later apologized to Cutler and the Bears organization. In a loss to the Saints this week, Cutler threw two touchdowns, three interceptions, and 194 yards for a season-low 58.0 passer rating. In the loss to Detroit, Trestman demoted Cutler in favour of Jimmy Clausen, but Cutler returned when Clausen sustained a concussion. Cutler completed 23 of 36 passes for 172 yards and a 63 passer rating in the Bears' season-opening season against the Vikings. He had 3,812 passing yards, a career-high 28 touchdowns, but led the NFL with 18 interceptions.

On January 19, the Bears recruited John Fox as their next head coach. Both Fox and GM Ryan Pace were initially lukewarm on Cutler, but they later agreed to keep Cutler as the starter. Martellus Bennett, the tight end, said his coworkers were unimpressive.

Cutler started the season off with a poor 225 yards in a loss to Green Bay, before he was sacking Bennett in last minute to bring his overall rating up to 67.5. He started Week 2 with 8 straight completions, but then threw an interception and pulled his hamstring, blocking safety Tony Jefferson from returning it for a touchdown. The Bears lost 48–23 to the Cardinals and were shut out 26–0 in Week 3 at Seattle, without Cutler. Cutler returned to Oakland after throwing two first half touchdowns and driving 48 yards in the last 2:05 to set up a game-winning field goal. In Week 5, Cutler threw two touchdowns in the final 3:05 for a dramatic 18–17 victory over the Chiefs and a tie for the most titles in team history. Despite a season-best 353 yards, a 4-point conversion, and a 69-yard drive in 17 seconds for a game-tying field goal in Week 6, Cutler fell short of his third straight appearance in Week 6. Cutler scored a go-ahead touchdown late in the 4th quarter after the bye, but the Vikings exploded for two late scores and a 23-20 victory. Cutler threw another late 4th quarter touchdown against San Diego in Week 9, beating the Bears for the first time in history (139). Cutler's 33-33 victory St. Louis was a tremendous effort, with three touchdowns (two of whom were for 80+ yards for the first time in franchise history) and no interceptions; his 151.0 passer rating was a career-best.

Both the 4–5 Bears and Cutler will be at their high point of the season. The Bears went 2-5 in the spring, with four of them losing by less than 7 points. Cutler won by a slim margin in three games, including narrow losses to Denver and San Francisco, as well as a narrow victory over Green Bay. Cutler led a 65-yard game-tying drive in the Broncos, but Bears running back Jeremy Langford was suspended on the two point conversion attempt, and the Bears lost 17-15. Cutler threw for 315 yards and two touchdowns against Washington, including a 50-yard completion with two minutes remaining, but Robbie Gould missed the game-tying field goal for a 24–21 loss. In a 38-17 loss to Minnesota that cost them 38–17, Cutler was fired five times and throw an interception, then had 156 yards but a 102 passer rating in a win over Tampa Bay, but had a 100.2 passer rating. Cutler scored two touchdowns in the season's finale against Detroit, but three interceptions, one deep in Lions territory at the 2nd warning, resulting in a 24-20 loss.

Despite his receiving unit being plagued by injuries, Cutler had one of his best seasons in 2015, with 3,629 passing yards, 21 touchdowns, 11 interceptions, and career highs in passer rating (94.3%) and completion percentage (64.4). The 11 interceptions were the lowest in his career and resulted in an interceptions percentage of 2.3, the lowest in a season when he has played at least 12 games, while 21 touchdowns were his second-most since 2011, with 3,629 yards being his third-most in his career. After completing 91 of 141 passes for 1,242 yards, seven touchdowns, and two interceptions, Cutler had a 103.2 passer rating (fourth in the NFL) on third down.

Dowell Loggains became the Bears' offensive coordinator after Adam Gase's resignation to become the head coach of the Miami Dolphins. In Cutler's first two games, he was sacked eight times and had two interceptions (where he suffered his right thumb but finished the game) and the Philadelphia Eagles (where he regained his injury and was replaced by Brian Hoyer). He skipped the next five games before returning to the Vikings, where he finished 20 of 31 passes for 252 yards, a touchdown, and a 100.5 passer rating en route to a 20-ten victory. Zach Miller lauded Cutler's return to work as well as mentioning that he delivered a half-time address to inspire his coworkers. In a loss to Tampa Bay, Cutler fumbled and threw two interceptions (including a pick-6). Cutler sustained a labrum injury in his throwing arm on November 20, 2016, a blow to the Giants that extended the remainder of the season. Cutler's five games in 2016 saw 1,059 passing yards, four touchdowns, five interceptions, and a 78.1 passer rating.

After the agreed years in his seven-year contract had come to an end, Cutler was released by the Bears under a $2 million buyout clause on March 9, 2017. The Bears decided to give Mike Glennon a $45 million contract despite Cutler's lackluster results and injuries. Cutler resigned from professional football in May 2017 and Fox Sports recruited him to be a commentator.

Ryan Tannehill, the Miami Dolphins' quarterback, sustained a season-ending injury on August 3, 2017, and the team reached out to the former Cutler. Cutler's one-year, $10 million deal with the Dolphins reuniting him with former Bears offensive coordinator Adam Gase, who was hired as Miami's head coach in 2016.

The Dolphins won their first game against the Los Angeles Chargers in Week 19–17. In the road win, Cutler was 24-of-33 for 230 yards with a touchdown to wide receiver Kenny Stills. Cutler sustained multiple cracked ribs during a Week 7 match against the New York Jets. Matt Moore was activated during the game and was ruled out of the Baltimore Ravens' game next week. In Week 9, he returned to face the Oakland Raiders. He was extremely effective in his 27-24 loss, going 34-of-42 for 311 yards and a touchdown. Cutler sustained a concussion in Week 11, which required him to miss the team's next game. In a Monday Night Football game against New England, Cutler outplayed Tom Brady and the Dolphins upset the Patriots, giving him his best showing of the year. In the victory, Cutler threw three touchdowns.

He said on December 27 that he would most likely resume his NFL career if he could be a starter, but "I wouldn't want to move or go somewhere just to back up." In the 2017 season, he played in 14 games and finished with 2,666 passing yards, 19 touchdowns, and 14 interceptions for the Dolphins. Cutler went 6-8 as a starter, and the Dolphins did not make the playoffs, and Cutler went 6-8 as a starter. During the season, several players, including receiver Kenny Stills, praised Cutler; Stills, referred to him as a "good guy." People in other countries have really abused him. I got to know him as a man and as a player, and I love him. I like him. I'm thankful for the opportunity of playing with him, and for him to get some balls."

NFL career statistics

Jay Cutler held at least 14 Bears franchise records as of 2022, including: the following:

Other franchise records (as of 2022)

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