The Best Second-Round Gems in Chicago Bears History (And How They Were Found)

The NFL Draft is quite the crap shoot. While each draft varies, teams usually hit on roughly 50% of their first round picks. That percentage drops to roughly 30-33% for players selected in the second round.

While second-round selections often come into the league with a ton of potential, only a fraction of the players make good on their team's investment in them. Conversely, each draft tends to feature a handful of players who fall through the cracks only to massively outperform expectations.

The Bears' second-round picks in recent years have produced a mixed bag. They've found some solid starters in Kyler Gordon and Luther Burden III, but have also had some misses in Teven Jenkins and Tyrique Stevenson (although his career has been a solid example of the ebbs and flows experienced by an average second-round pick).

Their overall history in the second round is a lot better, though. In fact, some of the most influential players in franchise history heard their names called in the second round.

Which players stand out among their peers as the best of the best? And how did the Bears land on them?

Bill George, 23rd pick in the 1951 NFL Draft

Bill George was the first linebacker to make a name for himself in Chicago. In fact, he was one of the first true "middle linebackers" across the entire league. The Wake Forest product caught the Bears' eye after making plays on all levels of their defense, as he also played along the defensive line. They thought highly enough of him to use a second-round pick on him, even though he had one year of college eligibility remaining (which was something they could do before the Super Bowl era. He wound up being well worth the wait.

George began his career in '52 and wasted no time in becoming one of the top 'backers in the league. He made eight consecutive Pro Bowls (back when it reallymeant something) from 1954 to 1961 and was named to the 1950s All-Decade Team. He became enshrined in the Pro Football Hall of Fame in 1974, and Chicago retired his jersey number (61) shortly thereafter.

Richie Petitbon, 21st pick in the 1959 NFL Draft

The Bears' decision to draft Richie Petitbon late in the second round of the 1959 NFL Draft wound up being a stroke of genius. He actually played quarterback at Tulane, but they thought his athleticism would allow him to seamlessly transition to defense. Petitbon played cornerback as a rookie before George Halas decided to move him to safety the following year.

He was selected to four Pro Bowls and achieved three All-Pro nods throughout his nine years in Chicago. Petitbon was a key defensive leader throughout the 60s and has the second-most interceptions (37) in franchise history.

Mike Singletary, 38th pick in the 1981 NFL Draft

Bears LB Mike Singletary on the sidelines at Soldier Field during the 1992 season. Photo by Imagn Images | RVR Photos-Imagn Images

The Bears' defense was solid in 1980, but they were still searching for their defensive identity. It didn't take them long to find it after selecting Baylor linebacker Mike Singletary in the second round of the 1981 NFL Draft. The back-to-back All-American was only on the board at that point due to being considered small for a linebacker, as he was one of the most productive linebackers in college football history to that point.

Singletary went on to have similar success in the pros, as he's one of the greatest linebackers in NFL history. He took the reins from Dick Butkus (and Bill George before him) and became a force in the middle of Chicago's (now utterly dominant with him as the shot-caller) defense. The '85 Chicago Bears wouldn't have nearly as much lore if Singletary hadn't gotten selected in '81. Singletary was named the NFL's Defensive Player of the Year twice, made ten Pro Bowls, and became enshrined in the Pro Football Hall of Fame in 1998.

Mike Brown, 39th pick in the 2000 NFL Draft

The Bears' 2001 season was one of the most miraculous seasons in recent memory (before 2025, anyway). Basically, they walked so last year's squad could run. The early returns for their 2000 draft class, which notably featured Mike Brown and Brian Urlacher, were a major reason for their success. Brown famously sealed back-to-back matchups over the 49ers and Browns with pick-sixes in overtime.

While no one was surprised to see Urlacher have immediate success, Brown's playmaking ability did turn some heads. Many thought he was too undersized to thrive at safety, which is a major reason why he was still available in the second round. Brown proved those doubters completely wrong, as he received two All-Pro nods during his time in Chicago. Injuries later took their toll and effectively shortened his prime, but he was one of their most impactful defenders early in his career.

Charles Tillman, 35th pick in the 2003 NFL Draft

Bengals RB Giovani Bernard rushes again Bears CB Charles Tillman at Soldier Field. Mike DiNovo-Imagn Images | Mike DiNovo-Imagn Images

Charles Tillman was a small-school standout ahead of the 2003 NFL Draft. He is the highest-drafted player in NFL history from the University of Louisiana-Lafayette. The Bears were looking to fortify their secondary and add a bit of toughness to their cornerback room, and they found the perfect man to do just that.

Tillman flew well under the radar throughout his career. He was rarely mentioned among the elite players at the position. However, that's a recognition that he certainly deserved in retrospect. He was an absolute turnover maven who got his hands on the football whenever possible. He has more than twice as many forced fumbles in franchise history (42) as the player in second-place all-time, Lance Briggs (19). He also sits third in franchise history in interceptions (36). I don't know if he'll ever make the Hall of Fame, but he's certainly deserving of the honor.

Devin Hester, 57th pick in the 2006 NFL Draft

Devin Hester was a positionless player coming out of Miami in 2006. He played both cornerback and receiver for the Hurricanes and, unsurprisingly, also displayed game-changing ability in the return game. He was still just scratching the surface as to what he could become there, though. No one had any idea that he'd be the greatest return specialist in NFL history in the pros, and he safely would've been off the board a lot early if they had.

Hester began his career as a cornerback before moving to the offensive side of the ball in his second season. While he never developed into a real weapon on offense, he did show promise there throughout his career. Still, Hester didn't make this list as a result of his pass-catching chops. He had an invaluable impact as a return specialist. He legitimately changed the game.

Matt Forte, 44th pick in the 2008 NFL Draft

Bears RB Matt Forte celebrates after scoring a touchdown at Soldier Field. Kamil Krzaczynski-Imagn Images | Kamil Krzaczynski-Imagn Images

Former general manager Jerry Angelo was on an absolute heater with his second-round selections from 2003 through 2008. Matt Forte was somewhat buried in one of the deepest running back classes of the 21st century. He may have been the sixth running back off the board, but you could make a strong case that he had the best career among all backs selected that year.

Forte was the engine that made the Bears' offense go throughout his seven-year tenure in Chicago. He is one of the most underrated running backs in NFL history, as his pass-catching chops were truly rare. Forte is one of only seven backs in NFL history to have both 9000 career rushing yards and 4500 receiving yards.

Jaylon Johnson, 50th pick in the 2020 NFL Draft

I had to include Jaylon Johnson on this list. He's easily their best second-round pick in recent memory, and will be remembered similarly to many of the players on this list if he can stay healthy and string together a few more solid seasons for Chicago. Johnson was considered one of the more pro-ready corners in the 2020 NFL Draft, and lingering concerns surrounding his shoulder injuries in college were the only reason he was still available for the Bears with the 50th pick.

Much like Tillman had done before him, Johnson has also flown under the radar throughout his career. However, he's been one of the league's best cover men whenever healthy since 2022.

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