Honestly, if you look at the Chicago Bears draft picks history, it’s basically a wild ride through a hall of mirrors. One minute you’re looking at arguably the greatest football player to ever lace up cleats—looking at you, Sweetness—and the next, you’re staring at a first-round quarterback who couldn't read a simple Cover 2 defense if his life depended on it. It’s a franchise that has drafted more Hall of Famers than any other team in the NFL, yet they spent decades wandering the desert trying to find one decent guy to play under center.
They've been at this since 1936. That year, they took Joe Stydahar with their very first pick. He ended up in Canton. Talk about setting a high bar. But for every Stydahar, there’s a cautionary tale. It’s a history built on ferocious linebackers, legendary "Monsters of the Midway" defenses, and a persistent, almost cursed struggle to figure out the quarterback position.
The Gold Standard: When the Bears Actually Nailed It
When the Bears hit, they hit like a freight train. You can't talk about the history of this team without mentioning 1965. It’s arguably the greatest single-round performance by any team, ever. They had the No. 3 and No. 4 picks. They took Dick Butkus and Gale Sayers.
Think about that.
In about ten minutes, they landed the most terrifying linebacker in history and the most electric running back to ever grace the grass. Both went to the Hall of Fame. Most teams hope to get one guy like that in a decade. Chicago got two in one afternoon.
Then there’s 1975. The fourth overall pick. Walter Payton. He wasn't just a draft pick; he became the soul of the city. But the savvy moves didn't stop in the first round. In 1983, the Bears used an eighth-round flyer on a skinny kid from Tennessee State named Richard Dent. All he did was become the MVP of Super Bowl XX and record 124.5 sacks. That’s the beauty of their better years—finding the cornerstone in the first and the legend in the eighth.
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The Modern Era and the QB Carousel
For a long time, the Chicago Bears draft picks history at quarterback was just depressing. It’s the elephant in the room. They traded a mountain of picks to move up one spot for Mitchell Trubisky in 2017, passing on Patrick Mahomes. You’ve heard that one a thousand times, and yeah, it still stings.
But things shifted recently.
The 2024 draft felt like a fever dream for Bears fans. After years of "good enough" or "maybe he'll develop," they finally pulled the trigger on Caleb Williams at No. 1. It was the first time since 1947 (Bob Fenimore) that they actually held the top pick and used it on a backfield star (they also had the No. 1 in 1941 but Tom Harmon didn't sign). Pairing Williams with Rome Odunze at No. 9 was the kind of aggressive, forward-thinking move fans haven't seen since the Ditka era.
The 2025 class kept that momentum going. Taking Colston Loveland, the tight end out of Michigan, at No. 10 overall showed a clear shift. They’re finally drafting for an explosive offense rather than just hoping the defense can win games 10-7.
Why the 80s Built the Legend
If you want to know why your uncle still wears a Mike Singletary jersey, look at the early 80s drafts.
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- 1981: They grabbed Singletary in the second round.
- 1982: Jim McMahon arrives at No. 5.
- 1983: Jimbo Covert at No. 6 and Richard Dent in the 8th.
That’s how you build a championship. It wasn't just luck; it was a specific identity. They wanted guys who were mean, durable, and slightly crazy. It worked. But then the well ran dry for a while.
The Busts That Still Haunt Halas Hall
We have to be honest: there have been some disasters. Cade McNown in 1999 was a mess from day one—bad attitude, weak arm. Curtis Enis at No. 5 in 1998 was supposed to be the next great back but never averaged more than 3.4 yards per carry.
And then there's David Terrell. Taken 8th overall in 2001. He was supposed to be the WR1 of the future. Instead, he became a symbol of the Jerry Angelo era's struggle to identify receiving talent. These picks didn't just hurt the roster; they set the franchise back years because they forced the team to overpay in free agency to fix their mistakes.
Finding Value in the Dirt
The Bears have a weird knack for finding Pro Bowlers in the middle rounds when they aren't overthinking it.
- Charles Tillman (2nd round, 2003): The "Peanut Punch" guy.
- Lance Briggs (3rd round, 2003): The perfect Robin to Brian Urlacher’s Batman.
- Mike Brown (2nd round, 2000): One of the most instinctive safeties to ever play.
- Devin Hester (2nd round, 2006): The greatest return man of all time.
When you look at the Chicago Bears draft picks history, these are the guys who actually sustained the "Bears Way." It wasn't always the flashy first-rounders. It was the grinders they found on Friday night of the draft.
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What Most People Get Wrong About Bears Drafts
People think the Bears just "can't draft offense." That’s not quite true. They drafted Sid Luckman in 1939 and he basically invented the modern T-formation quarterback. They drafted Johnny Lujack, who was a star before he retired early.
The problem hasn't been a lack of talent; it's been a lack of stability. They change GMs and coaches so often that a player drafted for a 3-4 defense suddenly finds himself in a 4-3, or a pocket passer is told to run a bootleg scheme. Look at Roquan Smith. Absolute stud, drafted 8th in 2018. He was great for Chicago, but they traded him away right as he was hitting his prime because of a "scheme fit" and contract philosophy. That’s the kind of move that keeps a team stuck in neutral.
Actionable Insights for the Future
If you're tracking where this team is going based on their history, keep an eye on these three things:
- The "Second Contract" Metric: The Bears have struggled to keep their own draft picks. Success in the next five years depends on whether Caleb Williams and Rome Odunze are still here in 2030.
- O-Line Continuity: In the 80s, they drafted Jimbo Covert and Keith Van Horne and left them there for a decade. They finally seem to be doing that again with guys like Darnell Wright.
- The Michigan/Big Ten Pipeline: Recently, there’s been a heavy lean toward Big Ten talent (Loveland, Zinter, etc.). This suggests a return to a "blue-collar" scouting identity.
The Chicago Bears draft picks history is a map of the city’s heart—full of grit, some legendary wins, and a fair share of "what if" moments. As they move into this new era with a legitimate franchise QB prospect, the ghosts of Cade McNown and Rex Grossman might finally be laid to rest.
The strategy is clear now: protect the investment. No more trading away three years of first-rounders for one veteran. The focus has returned to the draft, which is exactly where the Monsters of the Midway were born in the first place. You can see it in the 2024 and 2025 classes—they're finally building a house with a foundation, not just trying to paint a crumbling wall.