True 'underdog' Tim Jennings on his rise, Jay Cutler and what could've been in Chicago

He shattered the odds. The Bears CB is a shining light for all NFL hopefuls. In this Q&A, Jennings also laments the rings that got away, his QB's lack of leadership and what to do with Justin Fields.

Talent’s great. Talent can lead to plenty of notoriety and money and success.

But if anyone in recent Chicago Bears history knows that true hard work is more valuable, it’s cornerback Tim Jennings. He didn’t come from much. Hell, he didn’t even play football until 10th grade and this 5-foot-7 fighter at cornerback had to scratch ‘n claw for the final scholarship at his dream school: the University of Georgia.

The Indianapolis Colts drafted him in the second round of the 2006 draft, he won a Super Bowl as a rookie, played in another in 2009 and Jennings eventually busted out as one of the top playmakers in the NFL with the Bears.

In 2012, he led the NFL with nine interceptions, and he had 20 total in his 10-year career.

Always a threat to take it back to the house, Jennings made two Pro Bowls, too.

This defense was so, so close to ‘85 Bears-like immortality in the Windy City, too. In 2010, Chicago hosted the NFC Championship and lost to Green Bay with its quarterback injured on the sideline. And Jennings knows the 2012 team could’ve been special, too. Those Bears started 7-1, only to finish 10-6 and miss the postseason. One year later, the Bears missed the playoffs with one fourth-and-8 heave to Randall Cobb.

There were good times, and we certainly got into those good times.

But in his quarterback, Jay Cutler, the corner Jennings also saw why talent alone isn’t enough. He’s not shy in explaining why Cutler was a poor leader and a reason those Bears teams couldn’t break through. Thus, Jennings provides a unique perspective on the Bears of today and the latest handpicked savior: rookie Justin Fields.

These days, Jennings is coaching high school football part-time and doing defensive back training three days a week in northern Georgia. If he’s not training kids, you’ll probably find him on the golf course where he’s sure to text Brian Urlacher immediately after a great round.

We’ve welcomed plenty of Packers and Bears fans into our Go Long community this past month so here’s a chat with one cornerback who helped define that rivalry through the 2010’s.


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How long have you been training DB’s down there?

Jennings: I’ve been training in North Georgia since 2015. Just trying to focus on DB training — anywhere from middle school, high school to college — to get guys ready for the next level. I think a lot of kids are losing perspective of what it takes to get ready for the next level. Everybody wants to do it, but do they want to put in the work? When I was growing up, it was a lot different so I’m trying to give these guys those tools of what it takes. Me, being an underdog, I try to give these kids as much as I can. So I’ve been with a lot of guys in the North Gwinnett area — guys like Warren Burrell, who’s in Tennessee right now and Jordan Hancock, who’s signing with Ohio State.

That has to be great to see that work pay off with these two headed to big-time college programs.

Jennings: That’s why you do what you do. To see the development. To be able to develop them with some talent to get to the next level — maybe it’s not Division I, maybe it’s Division II ball — any way you can help a kid get to school somewhere, that’s the goal. That’s where you get your satisfaction: Helping these kids realize hard work does pay off.

You mentioned your own underdog roots. How steep of a climb really was it for you?

Jennings: It all started for me in Orangeburg, S.C. A real small town. But we were known for football in that area. I played at the rec age but didn’t think I had the size to play at the high school level. So I didn’t play my ninth grade year. I thought I was a basketball player — I was quick, I was fast. But I realized I wasn’t growing anymore, at 5-7, 5-8. That was my cap. I had coaches in my high school who helped me realize, “Hey, you’re athletic. I think you need to come out here on this football field and give it a try. You’re not going to be a 6-3 point guard who goes on to the next level and plays basketball in college.” So my 10th grade year, I finally went out and tried football.

We didn’t have all of this performance training in the early 2000’s so I had older guys I followed who were pushing and pulling tires in the backyard. Pushing trucks up the hill. Doing manual labor. So I followed those guys to show me what hard work and dedication was like. I modeled after that my 10th, 11th and 12th grade years and realized I was good. Schools were interested. Nothing major. I got a scholarship offer from South Carolina State right there in Orangeburg, S.C., so I said, “I might as well stay home and get this free education right here.” I decided to commit there but took a visit to the University of Georgia the week before Signing Day. Coach (Mark) Richt told me, “Hey, we don’t have any more scholarships left but if anything opens, you’re our guy.” The night before Signing Day, Channing Crowder de-committed.

So I de-committed from South Carolina State. It was more about having that exposure. Georgia was one of my favorite schools growing up because of Tim Wansley, a 5-8 corner and one of the best athletes I’ve ever seen at that size. So I followed Tim Wansley his whole career and became a huge Georgia fan. When my dream school gave me an offer, I said, “This is a no-brainer.”

I wasn’t afraid of the competition, me being a two-star against all of these four- and five-star athletes. I believed in my athletic ability and my ability to compete with the best. Being the last scholarship offer at Georgia and then being the first one drafted out of my class in 2005 says a lot about hard work.

A 10-year career is something I never dreamed of or believed in. I was just a small kid from a small town. That’s been my motto: Enjoying the moment and taking advantage of any opportunity that comes your way and making the best of it. That’s what I’m doing today, helping these young kids figure out what hard work really does — not just on the football field but it carries over to life itself. If you want it, you have to work for it. I don’t believe anything is given to you. You have to work for what you want.

What was that day-to-day “manual labor” really like?

Jennings: We’d have 18-wheel tires left in the backyard. We’d tie them to a rope and pull that as a sled. Dad’s pick-up truck just sitting there? We’d put that sucker in neutral and push it. That was our push sled. We had to figure out what we had in the backyard because we didn’t have the money to pay for expensive training.

A good childhood, though?

Jennings: Mom did as much as she could. Dad was always on the road. He was a truck driver. We didn’t live the most lavish life but it was never to the point where we couldn’t eat. I grew up in an environment where all I saw was my Mom and Dad work. To this day, my Mom still works. She’s a seamstress in Orangeburg, S.C. I was fortunate enough to let her live a little more comfortable but all she knows is work. I’m like, “Mom, you don’t have to work as hard!” She enjoys what she does and she’s been doing it for over 50 years. She’s been a seamstress for over 50 years so that’s all she knows. So sitting in the house and doing nothing would drive her crazy.

So that’s where I get my morals from. I’ve got to stay busy. Even though I’m retired from football, I’ve got to do something.

Thinking back, it seemed like whenever a play had to be made, you were the one making it. When we think back to the career of Tim Jennings, what do you want people to think?

Jennings: My career, man, it’s been an undersized kid who wasn’t highly recruited but he managed to overcome any obstacles that were there. Making plays that had to be made. My number was called, this was my opportunity.

Me playing in Chicago, I was playing with Charles Tillman, Brian Urlacher, Lance Briggs. So I’m going to get a lot of opportunities. Charles is a future Hall of Famer along with Lance and Urlacher — and then (offenses say), “There’s this undersized corner here we have to take advantage of.” Here’s your opportunity. What are you going to do with it? I rose up to the occasion which I had done my whole life. I had to believe in it — “You’re made for this. You’re here for a reason.” Early in my career, I was timid because I didn’t want to mess up. I didn’t want to get beat deep. I’d know it’s coming but want to just sit right here and just make the tackle. I had to grow up and realize, “No, you’ve got to make plays. There’s your opportunity right there. Believe it and it’s a pick-six.”

Once I believed in my athletic ability and believed in what I saw, there was no thinking then.

You need the guts. You read it in the report. Go for it.

Jennings: That’s it. That’s life. I was fortunate enough to play with Peyton Manning and Marvin Harrison and Reggie Wayne and Brandon Stokley and Dallas Clark. Practice was harder than anything I ever faced in Indy. We made it to the Super Bowl, won that, got to another one in 2009, lost to the Saints so I was blessed to get the feel of winning a Super Bowl and losing a Super Bowl.

I get to Chicago. I’m ready. I accept the challenge. You realize you’re here for a reason. So, let’s go. Let’s play.

That 2012 season comes to mind. I remember talking to you through that 7-1 start. You could do no wrong. Every week, somebody was picking off a pass and taking it to the house. How did everything click for you?

Jennings: I remember 2011 when I was in and out of the starting lineup. Coach Lovie (Smith) challenged me — “You’re there but you’re not making plays. We’ve got to make plays. We need to take the ball away. Getting turnovers on defense is what we pride ourselves off of.” So going into 2012, I knew it was going to be a good year for me. I had a great offseason where I was on the Jugs machine every day. I was ready for anything that’d come at me. Flying around that offseason I was making so many plays. Catching so many picks. And Lance Briggs said it to me in OTAs. He’s like, “You’re going to have a great year.” And I didn’t really believe him.

It was my third year in the defense so I was comfortable with what was going on. So once you get that confidence from your future Hall of Famers, oh man, it’s time to roll now. I’m one of them now. The confidence into that 2012 season, we were playing fast. We were playing lights out. We were out there doing what we do. Everybody was confident, man. And all the hard work I put in, I was ready.

Nine interceptions, led the league. There were some guys on my butt, too, like Richard Sherman and Patrick Peterson. And I finished in the Top 100 which I never thought could happen.

But with Jay Cutler and the offense — as a guy on defense having a season like that — it’s got to be frustrating that it didn’t lead to more. You guys went 10-6 but didn’t make the playoffs. That was a defense that could’ve won a Super Bowl.

Jennings: Yeah, yeah, we always look back. After that season, we lost Lovie. But that was the year we thought we had something special. We started off hot. But toward the end of the year, we got cold. That’s the opposite of what you want. It was disappointing but it says a lot about how the NFL works. It’s not how you start, it’s how you finish.

How do you stay mentally stable when you’re doing everything you can and there’s another interception thrown by your QB?

Jennings: There was definitely frustration there. I know I felt it from the older guys because they put in so much work and so much dedication. For me, personally, I didn’t want to let Lance down and Brian and Peanut down. My thing was, “Welp! Here we go again!” I need to go out and help these guys because I know they’re going to bust their ass. Of course, back then we were the Monsters of the Midway. We were a defensive-minded team. We had what it takes as a defense. My thing was, “Let’s get another takeaway and do what we do.” My thing was, ‘We’ve got to take the ball away but we’ve got to score.” Because obviously we see what’s going on over there (with the offense) but we can’t control that.

We can’t control what y’all do because we’ve got Brandon Marshall here, we’ve got Jay Cutler here, we know what type of guys they are. So, OK, I see what you guys are doing. Brandon was, “I need my catches. I need my yards. Jay, throw me the ball.” Seriously, that’s what they were on. It was always that tension over there. We didn’t have that mindset. We were just, “Let’s do what we do. Let’s run to the ball. Let’s create turnovers. Let’s score on defense.”

It got frustrating. And I could feel the frustration from the older guys as we went on and these games really meant something. The defense was doing what they’re supposed to but the offense couldn’t. We never clicked as a whole team, a whole unit and part of the reason was we had some “me” guys on the offensive side of the ball. To be honest with you, that’s what it was. We had “me” guys. And as a defense, it wasn’t about the individual. It was about, “Do your job that you’re supposed to do and this is the outcome it’ll be because this is how this defense works.”

Then, when you change that up and break up the Monsters of the Midway and this becomes an offensive-minded team? That’s why we never got over that hump.

That juxtaposition is fascinating. Urlacher. Briggs. Tillman. Julius Peppers was on that team. These are very serious dudes who grind. And then — for better or worse — Jay has that “don’t care” personality, where if I’m a serious guy on the other side of the ball, I imagine that’d drive you nuts.

Jennings: It did for some guys. The defense was still the heart and soul of the team so we were able to keep together what we did — that core we had. Some offensive players would hang out with the defensive guys. Jay wouldn’t. He was Jay.

Jay has always been Jay. Following Jay throughout his whole Vanderbilt career, we knew he had the talent. Starting off in Denver, he had the talent. But you have to understand, this is who he is. You can surround him with as much talent as you can. You’ve got a good defense. You’ve got a quarterback who can make all the throws. But if you don’t have that leader? At the quarterback position? It does trickle down a little bit. It’s going to affect what you do on offense.

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It’s the personality of your offense and, for a lot of teams, it is the personality of your team, right?

Jennings: That’s just the way it is. I played with Peyton Manning. There’s no way I’ve ever seen Peyton lose the confidence of his guys. It’s just not in his DNA. I’d see Peyton cuss out OC’s because this is not the way he does it. So, he demands that respect. He demands greatness. This is expected from him so he expects it from everybody around him. So watching Peyton and then seeing how Jay does things was night and day. You realize, “This is just who these guys are.”

How different are they?

Jennings: They are night and day. Peyton comes into work and he’s about his business. The whole day, he’s about his business. The Super Bowl year, he was about his business. There was nothing else. It was, “No, we’re not doing it that way. We’re doing it this way. This is a business trip. Family has their floor but we have our own floor. This is how we’re going to operate.” This is coming from Peyton telling Bill Polian: “No, sir, this is how we’re going to do it. Because we’re going on a business trip.” From that moment on, I knew that this was a whole different league. That was just why Indy had the success they had with Peyton Manning because he was a different type of leader. Like Tom Brady. Changing cultures of teams. It’s the way they carry themselves. It’s the way they lead. It’s not about, “I don’t care.” No. No. You better care.

What are your best war stories from Indy and Chicago? When you’re sitting around the bar with your buddies, what story comes to mind?

Jennings: That is the one. When we’re getting ready to go off to Miami for the Super Bowl and we’re having a team meeting. (GM) Bill Polian is telling us the itinerary of what’s going on. At first, we had a room to where we could have family and players on the same floor to get ready throughout that week because, “we still want you to be with family.” But Peyton was like, “No. We’re going to have a family floor and we’ll have a player floor.” That’s the whole week. “Families will be on this floor so if you want to see your family, go to that floor. But this is the players floor only, and that’s how we’re going to do it.” I looked at Reggie Wayne like, “Did that really just happen?” That’s the general, man. That’s the general speaking. Ever since then, I’ve looked at Peyton as one of the greatest to ever do what he’s done. I see why.

And Chicago was different. Now, it was more the defense getting people to buy in. I just enjoyed that defense so much. We were a family. We’d have gatherings and functions at Brian’s house and Lance’s house. We enjoyed each other and we played hard for one another. It was that chemistry that made you play just as hard for the guy next to you — and also for a guy like Lovie.

On the field — with Urlacher, with Briggs, with Tillman — any plays, any moments that still come to mind?

Jennings: The first one was a Green Bay game in 2010. I missed the tackle and forced (James Jones) back inside. And I see Lance and Brian just busting their ass over there to make the tackle and strip the fumble and I was able to fall back on the ball. (To set up the game-winning field goal.) That just summarized what this defense is about and what these guys are about and “Tim you better bust your behind and make these plays because these are the guys you’re playing with. If you’re going to miss this tackle, you better make sure you’re missing it at the right angle, the right way, because they’re coming.” In my mind, I just f----- up. I missed the tackle. I’ve gotta make up for it. The ball came out and I was in the right place because I didn’t give up on the play.

What is going to happen next with the Bears? They took their swings at Russell Wilson, Deshaun Watson and would’ve even been in on Ben Roethlisberger. Every quarterback. And they ended up what seems like a potentially great one in Justin Fields. Should there be hope in the air or more gloom and doom?

Jennings: I’m one of those guys, you have to show me. Show me your potential, show me who you are and I can make a better assessment. You can look good on paper but it’s a year-to-year league. … Chicago went to the Super Bowl with a great defense and had Rex Grossman as its quarterback. Yeah, the quarterback plays a major part but what’s your identity? What’s your identity as a team and find the right players to buy into that identity. That team. That motto.

Is Fields the guy? We don’t know yet. You know the city of Chicago. They’re going to either love you or hate you. When things get tough, is he the kind of kid that can stay positive and get through those rough moments? Because it’s not an easy city to win over the fanbase. You’ll have to do something and be consistent at it. Show me.

A young kid like Justin Fields, I don’t want the stage to be too big for him. Don’t throw him out there if he’s not ready because the city wants it so bad and now you just ruined another young quarterback’s career. That’s just me personally. I don’t want him to be another guy. Is he a good quarterback? I think he’s a good quarterback. Is he a great one? I don’t know yet. Is he the answer for Chicago? I don’t know. … I’m never going to put too much pressure on any guy, especially as a rookie. It took me four years to come into my own. He doesn’t have that time. People are expecting this now.

Maybe Jay’s personality was great in that city — when you sincerely don’t give a shit what anybody says — but then it’s a bad thing because those vets on defense would like for you to care a little more.

Jennings: What you saw with Jay on the field, that’s how he was in the locker room. That’s not good. That’s not good being a leader. If you’re a leader, you’ve got a leader and you’d know what you have in Justin. You’ve got to win over that locker room and that building first. As you win games, then you’re going to win the fan base. For me, I didn’t think Jay was ever that guy. Watching him at Vanderbilt, I didn’t think he was ever that guy. I never thought he was that leader. I don’t know if the scouts thought differently. They probably saw talent. But I don’t think he was ever a leader. So when Jay got in the locker room, that’s who he was! Now if you’ve got a guy in young J. Fields and he’s been that guy at Ohio State, then OK. That’s what we need right now.

When you’re in the locker room, what does that really look like? Because “leadership” can be a pretty nebulous thing. We throw that around and people don’t really know what that means. So, when you don’t have that at that position, what does it look like?

Jennings: To me, as a defensive player, I’m not in meeting rooms but I hear stories. Even when Brandon Marshall was there, every pass play can’t go to Brandon. It just can’t. He’s just not supposed to do that. It’s not supposed to be that way. And then leadership as far as how I see you at practice. On defense, I can see how you react to guys and how you’re coaching them up. How you’re teaching. Even if you make a bad mistake, trying to correct that. There’s a lot you can see on the practice field — “What went wrong here? How can we get this better?” Even being perfect. I keep going back to when I played with Peyton Manning. I just remember when I practiced against Peyton Manning and all those guys, I rarely saw an incomplete pass. The ball never hit the ground. And there weren’t too many interceptions. And that’s just a true story. If it did, there were corrections being made. Like, “Hey, Marvin, you might want to be here. If he’s there, you need to be here.” So, that’s what it looks like.

And in Chicago, it’s basically f--- it mode?

Jennings: Yeah, it was a little different! It was a little different from going through that and seeing this. I guess you can be leaders in your own way. I’ve heard that before. But some people respond to certain things certain ways, and you have to lead in ways that guys will respond to.

It’s such a lesson for all GMs, right? Here’s a guy with all the talent. He could make every throw. But this other stuff matters because you guys had the team around him to win Super Bowls. And this leadership can get overlooked. I guess we’ll see if Justin Fields has it. That might matter more than anything.

Jennings: We had that defense. We had all the pieces to get to the Super Bowl. I guess we were just missing the quarterback. Now you’re straddling the fence, though. Do you give up that for more talent because you’re going to lose something? But let’s not lose the fact that you got to the Super Bowl with (Grossman). And then you had a running game. That running game is crucial. We had Matt Forte but you’ve got to make sure you have the right leader at quarterback to get us over the hump.

But it was a hell of a career. Small town. Two stars. Overlooked. When you look back, it has to feel good.

Jennings: This is what I’ve been doing my whole life, my whole career. Yeah, it was a great career. I enjoyed every moment of it. But it’s really all I knew. This is how I was raised. I needed to be ready for the opportunity because this is how I was grown to be. My level of expectations were always high because I’ve been that underdog. I knew I had to play at a certain level. My expectations are always at a certain level. Because it’s been instilled in me with my Mom. It was always fun and when it wasn’t fun, I knew I had to find something else.

So there was a time when it wasn’t fun anymore?

Jennings: Yeah, I kind of lost the fun for it. In Chicago, playing with that defense and playing with Lovie, that was a kid’s dream. For me to be there was great. Then, I lost Brian. I lost Lance. I lost Peanut. And you kind of put me in position to be that guy. And having Marc Trestman come in there — “Hey, Tim, you’re the leader for us now.” We’re an offensive-minded team with Brandon Marshall, Jay Cutler, Marc Trestman. So it’s now becoming, “What? This is different.” Now, this game is becoming a business. You’re making “X” amount of dollars so your expectations become higher. The money was good but changing the whole culture — which was successful here and for me — now that’s all gone? And I have to be this guy? The business took the fun out of it.

It was all bad. It was weird. I don’t know what culture they were going to but it wasn’t the Bears Way. He didn’t have the guys to do it. You had to really revamp that whole team to see Trestman’s culture. The good thing is Chicago realized, “We don’t have time for that.”

As someone molding the next generation of DB’s, is there someone in the game today you really admire?

Jennings: I like consistency. There’s talent all over the board now. Patrick Peterson is definitely still one of the best corners in the league. He’s been doing it for a long time on a consistent level. That is very hard to do — very hard to do. You’ve got young corners like (Jason) Verrett in San Fran. I love his game. I grew to be a big Kyle Fuller fan. I played with Kyle. Kyle definitely is a top 10 corner in the league. He just needs to be put in the right system. He can play. He was ahead of the game. In Year 1, Year 2, he was really Year 10. Jalen Ramsey grew on me over the years. I like (Jaire) Alexander in Green Bay a lot.

Once you get in that league, then I like to see flashes. You have to show me. I’m not big on you coming out of college with all this hype. Because for me, personally, I never believed in that. Being two-star, I’m going to beat a five-star player. I like the underdog story. LeBron James, you’re supposed to be all-world. You were No. 1 when you came out of your Mom’s womb. You’re supposed to be all that. I like the guys with the underdog story who had to work a little bit. Overcome some adversities in life. That’s me. You have to show that you can play this game on a consistent basis and be a Patrick Peterson. Being in Year 12 and 13 and playing at a high level? That’s hard.

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