Selected third overall in the 2014 NFL Draft out of UCF, Blake Bortles landed in Jacksonville carrying the weight of a franchise desperate for a savior. The 2013 AAC Offensive Player of the Year brought ideal physical tools—a prototype 6-foot-5 frame, a strong arm, and deceptive mobility—and was thrust into the fire earlier than planned during his rookie year. That introductory campaign brought steep growing pains, as he absorbed 55 sacks and threw 17 interceptions while throwing just 11 touchdowns.

His sophomore season in 2015 produced a statistical explosion that teased superstar potential. Operating a high-octane passing game, Bortles set Jaguars single-season franchise records with 4,428 passing yards and 35 touchdown passes. Yet that production came with heavy volatility; he also led the NFL in interceptions (18) and sacks taken (51). He backed up that wild ride by throwing for 3,905 yards in 2016 and 3,687 yards in 2017, demonstrating durability while quietly proving to be an effective weapon on the ground as a scrambler.

The absolute high-water mark of the Bortles era arrived during the magical 2017 campaign. While a dominant, sack-happy defense carried the primary identity of the "Sacksonville" squad, Bortles executed his role as a game manager to near perfection. He steered Jacksonville to a 10–6 record, an AFC South division title, and a memorable postseason run. In the playoffs, he played mistake-free football, defeating Buffalo and outdueling Pittsburgh on the road to push Jacksonville within one quarter of the Super Bowl in the AFC Championship Game against New England.

That playoff run earned Bortles a contract extension, but the momentum evaporated instantly in 2018. Mechanical struggles, turnover issues, and a wave of offensive injuries caused the team to slide, leading to his benching in favor of Cody Kessler. The breakup was finalized in March 2019 when the Jaguars released him shortly after signing Nick Foles. Bortles backed up Jared Goff with the Rams and had brief roster stints in Denver, Green Bay, and New Orleans before officially announcing his retirement in 2022.

In his five seasons in Duval, Bortles threw for 17,649 passing yards, 103 passing touchdowns, 75 interceptions, and 1,766 rushing yards with eight rushing touchdowns.

Fresh off a 1997 national championship season at Michigan, offensive tackle Maurice Williams was selected by Jacksonville in the second round (43rd overall) of the 2001 NFL Draft. Placed right into the fire, the 6-foot-5 lineman claimed the starting right tackle spot in training camp and went on to start all 16 games as a rookie.

Williams became a bedrock piece of Jacksonville's offensive line throughout the 2000s, forming a crushing right side alongside interior guard Vince Manuwai. Though quietly effective away from national media headlines, Williams' mobility and strength were vital in opening lanes for tailback Fred Taylor during peak rushing seasons, including the 2006 team that piled up a franchise-record 2,541 rushing yards. Demonstrated by his willingness to shift to right guard or step in at left tackle when injuries struck the unit, his versatility kept him in the starting lineup across nine seasons in North Florida. Compounding bicep and knee injuries eventually hampered his durability toward the end of his run, but his near-decade of work on the line remains one of the longest tenures by a tackle in franchise history.

He started 100 of his 105 games.

Donovin Darius was chosen in the first round (25th overall) of the 1998 NFL Draft, establishing a reputation as a fierce, impactful enforcer. Coming from Syracuse, where he was named Big East Defensive Player of the Year, the Camden, New Jersey native quickly introduced physical dominance to Jacksonville's secondary. From his first day on the field, Darius earned PFWA All-Rookie Team recognition, leading all Jacksonville defensive backs with 108 tackles as a rookie.

That debut performance established a template for near-decade-long dominance at safety. Operating primarily as an in-the-box strong safety, Darius functioned like an extra linebacker, relentlessly coming downhill to blow up interior running plays while delivering punishing hits to receivers braving the middle of the field. His downhill aggression set the physical tone for Tom Coughlin's playoff-bound rosters in the late 1990s and remained a constant as Jack Del Rio built his defensive unit in the mid-2000s.

While accolades often eluded him on the national voting stage, Darius' value inside the locker room and on the field was unquestioned. His defining hallmark was baseline consistency: if Darius was healthy enough to put on his helmet, he started. In fact, across nine active seasons in Jacksonville, Darius started all 115 regular-season games he appeared in for the franchise, never spending a single contest coming off the bench.

Beyond his crunching tackles, Darius displayed sharp ball instincts, racking up 14 interceptions and six fumble recoveries in a Jaguars uniform. He was an integral piece of Jacksonville’s 1999 squad, which finished an NFL-best 14–2 and reached the AFC Championship Game. Even through coaching shifts, scheme changes, and injuries later in his career, he remained the emotional heartbeat of the secondary.

After nine seasons, Darius' run in Jacksonville ended in June 2007 when the team released him to usher in a younger defensive core. He closed out his NFL career with a brief three-game stint with the Miami Dolphins before retiring.  As a Jaguar, Darius compiled 618 combined tackles (479 solo), 14 interceptions for 189 return yards, 46 passes defended, seven forced fumbles, six fumble recoveries, and 2.0 sacks.

Before securing the biggest contract in Jacksonville franchise history at the time, offensive tackle Leon Searcy established his credentials as a three-time national champion at the University of Miami and a starter for the Pittsburgh Steelers in Super Bowl XXX. Signing with the Jaguars in 1996 as the prized target of their free-agent class, the former first-round pick brought immediate toughness and championship swagger to the right edge of North Florida's offensive line.

Searcy served as an unyielding pass protector and run-blocker, starting all 63 of his regular-season appearances in teal and black. His heavy hands and mobility kept quarterback Mark Brunell upright while carving wide lanes for Fred Taylor, fueling Jacksonville's rise to a premier AFC contender. Searcy's tenure peaked during the legendary 1999 season, anchoring a front five that allowed just 23 sacks all year on the way to a league-best 14–2 record. That stellar campaign earned him Second-Team AP All-Pro honors and a Pro Bowl selection. However, misfortune struck when a severe leg injury during 2000 training camp sidelined him for the entire season. He subsequently signed with the Baltimore Ravens in 2001, but a preseason injury kept him from ever appearing in another regular-season game.

He started all 71 of his games (63 regular season and eight postseason) in Jacksonville.