My All-Time Historical Bears Team: The Gary’s Bears

A few weeks ago, an idea was proposed to our staff to have a fantasy draft, with the draft pool consisting of all current and former Chicago Bears. Being a huge fan of fantasy football, I jumped at the idea. To me, this seemed like the ultimate fantasy lineup-building exercise.

There were a total of 25 rounds, in total we would draft 11 offensive starters, 11 defensive starters, a kicker, a punter and a special team contributor of our choice.

I’m here to explain my drafting strategy, break down my picks,

and make my case as to why my team is the best of the 8 drafted.

So without further ado, I present: The Gary’s Bears.

My Picks

In a snake draft format, I was given the 7th pick, and in my eyes it’s always better to be closer to #1 or #8, as the near back-to-back picks allows you to double up on value, and while being 7th might see a drop off of top end talent, it allows you to tackle needs better with better talent overall across the roster.

My picks were as follows:

• R1, Pick 7: QB, Jay Cutler
• R2, Pick 10: MLB, Mike Singletary
• R3, Pick 23: WR, Alshon Jeffery
• R4, Pick 26: LT, Jimbo Covert
• R5, Pick 39: FB, Rick Casares
• R6, Pick 42: WR, Johnny Morris
• R7, Pick 55: RT, Keith Van Horne
• R8, Pick 58: TE, Greg Olsen
• R9, Pick 71: LG, Mark Bortz
• R10, Pick 74: RG, Ray Bray
• R11, Pick 87: C, Dan Neal
• R12, Pick 90: DE, Ed O’Bradovich
• R13, Pick 103: CB, Bennie McRae
• R14, Pick 106: SS, Shaun Gayle
• R15, Pick 119: DT, Alan Page
• R16, Pick 122: FS, Danieal Manning
• R17, Pick 135: DT, Jim Flanigan
• R18, Pick 138: RB, Jordan Howard
• R19, Pick 151: K, Cairo Santos
• R20, Pick 154: LB, Danny Trevathan
• R21, Pick 167: CB, Terry Schmidt
• R22, Pick 170: DE, Bryan Robinson
• R23, Pick 183: LB, Warrick Holdman
• R24, Pick 186: ST, Brendon Ayanbadejo
• R25, Pick 199: P, Maury Buford

My Drafting Philosophy

The Chicago Bears have a rich history on the defensive side of the ball, perhaps the richest in NFL history. Unfortunately, that rich history never really translated to the other side of the ball, and outside the offensive line and running back positions, the Bears have spent most of their 100+ year history struggling to find talent.

My plan was simple: Focus on the offense, drafting them early and often to soak up as much of the franchise’s talent on that side of the ball as possible, and then fill the roster with strong defensive picks who were productive in their time with the Bears, as per the rules of the fantasy draft, you assume that production carries over to modern day. Then, anchor it with arguably one of the best MLB’s in NFL history. I did just this, as 11 of my first 12 picks all went to the offensive side of the ball.

I drafted my quarterback first round, knowing that I did not want to be stuck with essentially any quarterback outside of maybe three guys in our history, surround him with playmakers, and stack the offensive line, not only protecting my quarterback, but also giving my backfield duo a fantastic line to block for them.

Gary’s Bears Offense

• R1, Pick 7: QB, Jay Cutler
  • I had my eyes on one of two quarterbacks, Caleb Williams or Jay Cutler. And with Caleb going second overall, I was more than happy to find myself with Cutler at pick 7. Depending on how you look at things, Cutler is the franchise’s best quarterback, leading it in completions, yards, touchdowns, 4th quarter comebacks, and game-winning drives. Until Williams was drafted by the Bears in 2024, he possesses the most arm talent of any Bears quarterback to ever lace them up.
• R18, Pick 138: RB, Jordan Howard
  • Most of the higher-end running backs were off the board early, but my logic was to build out the guys in front of your Running Back to make him that much better. Look at the dividends the investment in the line paid for Swift and Monangai just this past year. Howard spent just three years with the Bears, but he was steadily productive in that time averaging 1123 yards and 8 touchdowns a season. He shined in his rookie year, going for 1313 yards, good for second in the league and earning a Pro Bowl trip for it.
• R5, Pick 39: FB, Rick Casares
  • One of the most unheralded Chicago Bears, in my opinion. The 6’2″, 226-pound Casares rushed for over 5,500 yards in his 10 seasons with the Bears, and retired as the Bears’ all-time leading rusher, as a Fullback. In 1956, he led the league in rushing and rushing touchdowns, going for 1,126 yards and 12 scores, earning him a trip to the Pro Bowl (he would make 4 more in his Bears career) and All-Pro considerations. With the offensive line I have assembled, Cesares will have no issue punishing the 2nd and 3rd level defenders.
• R3, Pick 23: WR, Alshon Jeffery
  • Alshon Jeffery was one mildly productive season from being the franchise’s all-time leading receiver, as he finished his Bears career just 510 yards shy of WR Johnny Morris (more on him later). Alshon also finished 9th all-time for receiving touchdowns for a Chicago Bear. He was selected to 1 Pro Bowl as a Chicago Bear, where in his 2013 season he recorded 89 receptions for 1,421 yards, and 7 touchdowns, and could have arguably been elected to a second one in 2014, where he posted 85 receptions, 1,133 yards, and 10 touchdowns. He also owns the franchises record for receiving yards in a game, when he went for 249 yards against the Vikings. The tall, big-bodied receiver with strong hands gives the offense a true X receiver.
• R6, Pick 42: WR, Johnny Morris
  • The franchise’s leading receiver landed in my lap, and I couldn’t resist giving my Quarterback two top receiving threats. Morris claimed to have run a 4.35 40-yard dash and was considered one of the league’s premier serious threats. His 1964 season was one for the ages, where he became one of six players at the time to win the NFL receiving Triple Crown, hauling in a then-NFL record 93 receptions (in 14 games) for 1,200 yards and 10 touchdowns. His season landed him 4th in MVP voting and earned him All-Pro consideration. His speed and versatility make him a perfect Z receiver.
• R8, Pick 58: TE, Greg Olsen
  • Greg Olsen was well on his way to becoming this franchise’s most prolific pass-catching tight end, but 2010 came along, as did Mike Martz with it. Martz famously undervalued the Tight End position as pass catchers, and after coming off a 2009 season where he led the team in targets, was 3rd in yards and lead them in touchdowns with 8, his target share and production saw a sharp 33% decrease and he was shipped off the following year to the Panthers. Olsen was Cutler’s favorite and most reliable target during their shared tenure in Chicago. And with some higher priority Tight Ends off the board already, it made sense to give Jay his ultra-reliable security blanket.
• R4, Pick 26: LT, Jimbo Covert
  • Along with leading the franchise in so many passing categories, Jay Cutler also led the franchise in sacks taken, being sacked 251 times in his years with the Bears, an average of nearly 32 times a year. This is why protecting Cutler’s blindside is so important. In his time in Chicago his best Left Tackle he worked with was a washed Orlando Pace in 2009, who played just 1 season with Cutler. Covert is widely considered the franchise’s best left tackle. He made 2 Pro Bowls and was named All-Pro twice, while, of course, being elected to the Hall of Fame. Famously over his career he faced Hall of Famer Lawrence Taylor three times and did not allow him a single sack. Good luck trying to come off the blind side on Jimbo.
• R9, Pick 71: LG, Mark Bortz
  • Bortzilla rounded out the three linemen I nabbed from the vaunted 80’s era line in round 9. The 6’6″, 282-pound Bortz was a staple of the offensive line for 12 seasons with the Bears, playing with a physical edge, especially in the run game, earning his nickname. He earned two trips to the Pro Bowl and played in 171 games with 155 starts. A perfect fit to clear out the running lanes for my big thumpers behind him, allowing them to get to the 2nd level with ease.
• R11, Pick 87: C, Dan Neal
  • Dan Neal walked so Jay Hilgenberg could run. Neal spent 9 seasons with the Bears, helping Walter Payton rush for career highs in yards and touchdowns in the 1977 season. In 1981, Hilgenberg was a mere undrafted rookie playing behind the veteran Neal, by 1983 Hilgenberg was ready to take the reins, and the tutelage of Neal helped Hilgenberg become one of the best Centers in team history. Neal’s importance of the Bears was represented by being named the Bears’ Offensive MVP in the 1978 and 1980 seasons. One of the more underrated linemen in Bears history, and one I was happy to grab to have as my man in the middle.
• R10, Pick 74: RG, Ray Bray
  • Bray was a key member of the Bears teams of the 1940s that won four NFL Championships, three of which Bray was a part of. He missed the fourth championship because, in the prime of his career, he was focused on winning the World Freedom Championship by kicking Nazi butt after leaving football to serve in the United States Navy from 1943 to 1945. When Bray returned to the Bears, he picked up right where he left off, earning two Pro Bowl selections and two Second-Team All-Pro honors. (He had already made the Pro Bowl twice before enlisting.) An ass kicker on and off the field is the type of guy I want on my offensive line.
• R7, Pick 55: RT, Keith Van Horne
  • Van Horne represents the second lineman I drafted from the era of offensive line that is considered the best in Bears history. Anchoring the right side of the offensive line for 13 seasons Van Horne appeared in 186 games, 169 of those starts. That’s nearly 10 straight seasons of high-level play out of your right tackle, and the 186 games played is the second-highest mark for any Bears offensive lineman all time, second only to Olin Kruetz’s 190. Locking down the edges of the offensive line early for me was important, allowing Cutler all the time he needs to find his targets deep.

Gary’s Bears Defense

• R12, Pick 90: DE, Ed O’Bradovich
  • O’Bradovich had a slow start to his Bears career, recording just 8 sacks in his first 5 seasons. But over the last 5 years of his career with the Bears, he averaged nearly 9 a season, topping 10 twice in back-to-back seasons in 1967 and 1968. The 7th round pick O’Bradovich finished his career 32nd all-time in career approximate value, and 7th in sacks, recording 51.5 in his 10 seasons with the Bears. He also had a nose for the ball, recovering 13 career fumbles. When asked about his teammate, Dick Butkus had this to say about O’Bradovich: “Just to hit people wasn’t good enough. He loved to crush people.” A strong endorsement from one of the games’ best.
• R15, Pick 119: DT, Alan Page
  • The judiciary of the “Purple People Eaters” joined the Chicago Bears in the twilight of his career. After being waived in 1978, he joined the Bears and immediately recorded 11.5 sacks in 10 games with them. In his four seasons to close out his career with the Bears, he netted 40 sacks, 1 interception, 4 fumble recoveries, and 1 safety. It took him just 4 seasons, at the tail end of his career, to finish 13th all-time in sacks for the Bears, getting 10 sacks a season from your DT? I’m more than happy with that. And add in the tenacity with which Page played with, good luck stopping him.
• R17, Pick 135: DT, Jim Flanigan
  • I couldn’t resist picking Flanigan. As a kid, he was one of my favorite players, and I always enjoyed the juxtaposition of him being a Green Bay, Wisconsin native forcing to punish the Green Bay Packers. In his 7 years with the Bears he recorded 40.5 sacks, good for 12th all time, including 11.0 in 1995, 3rd most of any DT that year. He also forced 6 fumbles while recovering 7. I feel like Flanigan doesn’t get much fanfare due to the period he played in, as the 90’s were a pretty miserable time for the Chicago Bears. But Flanigan was dependable (74 consecutive starts between 1995 and 2000) and produced at a good level, especially for an interior lineman, recording nearly 6 sacks a year.
• R22, Pick 170: DE, Bryan Robinson
  • Robinson was an important piece of the 2001 Bears defense. In his 6 years with the team he recorded 16.5 sacks, 5 forced fumbles, 231 tackles, and one of the biggest reasons why I added him to the squad: 27 passes defended. Robinson was well known for his wingspan, and commonly batted thrown balls at the line, this also came in use in place kicking, where he had 1 official block and influenced the middle of the scrum with his vertical wingspan. While not a top end Defensive End, he adds some unique ripples to the defense.
• R20, Pick 154: LB, Danny Trevathan
  • While Trevathan played in a 3-4 defense, there’s no rule saying I can’t slot him into a Linebacker slot and experience any fall off due to it! Trevathan was a big part of the mini-resurgence of the late 2010’s Bears defense, and was captain of the extremely notable 2018 defense. He was solid in coverage, defending 21 passes in his 6 years as a Bear, while also chipping in 3 interceptions. He also forced 4 fumbles, recovered 2 and recorded 459 tackles. Slotting him next to Singletary should only elevate his game, giving us a Lieutenant General to Singletary’s General of the Army.
• R2, Pick 10: MLB, Mike Singletary
  • I had my QB on offense in round 1, I knew I needed to jump at grabbing my QB for the defense. Samurai Mike is be the best person to suit that. A 10x Pro Bowler, 7x All-Pro, 2x AP Defensive Player of the Year, and a Hall of Fame induction. Known for his on-field intensity, he is often labeled as the “heart and soul” of the Bears defense during his time roaming the gridiron, and according to PFR, the second most valuable Chicago Bear of all time, second only to Walter Payton. Simply having Singletary on the field elevates the play of the defense around him.
• R23, Pick 183: LB, Warrick Holdman
  • Holdman may be one of my favorite unheralded Linebackers in Bears history. He played the WILL Linebacker next to Brian Urlacher and was a steady force in pursuit and gap closing, he also excelled in pass coverage (15 passes defended in his 5 years with the Bears.) By slotting him alongside a Linebacker on the same level as Urlacher was in Singletary, I envision Holdman’s game elevating much like it did in 2001, where he recorded 109 tackles, 1 interception, 1.5 sacks, and 9 passes defended.
• R13, Pick 103: CB, Bennie McRae
  • McRae was a former track star and was actually named team captain for the 1968 season, showcasing his speed and leadership. And when he became a Bear, Bennie McRae produced. He recorded at least 1 interception every season of his 9 years with the Bears, averaging three interceptions a season, totaling 27 in his career, four of which he returned for touchdowns, the franchise record when he retired. He was a key piece of the 1963 Chicago Bears championship team, nabbing 6 interceptions and returning one for a score that year. He also earned 2nd Team All-Pro honors in 1965. While not a lockdown corner, he provides good ball hawking ability, and dependable coverage.
• R16, Pick 122: FS, Danieal Manning
  • Manning played 5 seasons with the Bears, grabbing 7 interceptions, forcing 6 fumbles while recovering 2, and recording 345 tackles. A lot like Shaun Gayle, Manning provided versatility by playing both Safety spots, while also being able to play Nickel. He also added the versatility of being a good kick returner, he led the league in kick return average in 2008 with a 29.7 yards per return. He makes a versatile duo with Gayle next to him, allowing some exotic defenses to attack opposing offenses with.
• R14, Pick 106: SS, Shaun Gayle
  • Shaun “Smoke” Gayle was a good Strong Safety for a long time for the Bears. Originally drafted in the 10th round of the 1984 draft, while Gayle’s bulk of his starts came from the Strong Safety position, he could fluidly play any position in the secondary, a Swiss army knife of the third level. He would go on to record 11 interceptions, 6 forced fumbles, 9 fumble recoveries, and 625 tackles in his time as a starter, while earning a Pro Bowl nod in 1991.
• R21, Pick 167: CB, Terry Schmidt
  • Another unheralded Bears defender of yesteryear. Schmidt’s approximate value during his 9-year career with the Bears equaled Eddie Jackson’s (who went to two Pro Bowls and was named All-Pro once). Schmidt spent his first two seasons as a depth Cornerback before getting his chance to start. He responded by collecting three interceptions on average a season for a total of 21 over his time as a starter. He also returned two of those for touchdowns. He was also remarkably durable, starting 73 straight games at Cornerback. Much like McRae, Schmidt provides good ball skills and an elevated ability to create turnovers.

Gary’s Bears Special Teams

• R19, Pick 151: K, Cairo Santos
  • When you’re kicking in Chicago off the lake, the most important thing for kickers is ACCURACY!! We have seen so many kickers come into Chicago, both as opponents and on our own sideline, struggle with the lake effect winds, which often end up swirling inside the stadium. Cairo Santos might not have the biggest leg in the NFL, but he is the most accurate kicker in Bears history (88.3%) and is 4th all time in Chicago Bears scoring, on pace to pass Walter Payton next year. Ensuring our ability to maximize scoring aligns with the identity of my draft.
• R25, Pick 199: P, Maury Buford
  • I needed a punter. Buford is 5th all-time in Bears history in punt yards and 7th all-time in Inside the 20 % (of punters who have attempted 100+ punts in their Bears career) With my offense, the immortal words of Caleb Williams rings true here “You’re not going to punt too much here.” But having a guy who does well in pinning you in your own end helps a lot when you do need to punt.
• R24, Pick 186: ST, Brendon Ayanbadejo
  • When I think of ace special teamers, Brendon Ayanbadejo always comes to mind first. He played three seasons in Chicago, recording 82 special teams tackles in that time frame. His level of play earned him two trips to the Pro Bowl in 2006 and 2007. His lockdown ability on coverage teams will go a long way in helping us better flip field position (on the rare occasions we do have to punt!)

While my defense may run about middle of the road, I feel like the top-end offensive talent I managed throughout the draft is more than enough to make up any slack created. That said, the defense should still be a fairly productive defense. When taking the yearly averages of the players and their time spent with the Bears, we can expect to see 12.1 Interceptions, 29.5 sacks, and 11.9 fumbles forced, with about that many recovered.

A solid defense to round out the elite group of players on offense.

You can check out our full draft here.

Once all eight teams are announced, we’ll hold a tournament and ask you, the WCG readers, to pick the winner.

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Gary Baugher Jr. is a 2nd year contributor to WCG, bringing football insight backed by over 16 years of experience in organized football and more than 30 years as a passionate fan of the game. You can follow him on Twitter at @iamcogs.