"Being a Bear would have been fantastic," Kittle shared on ESPN Chicago's Waddle & Silvy show. "I'm pretty happy with where I ended up. Doing pretty well for myself out here in San Francisco. But the Bears are always dear to my heart, and the Cubs. I've got to get back to Wrigley.
"But, hey, you know what it is? That's the draft. All these guys, they say they have a chip on their shoulder. All these teams looked past me. I got drafted in the fifth round. All 32 teams looked past me for five rounds. It is what it is.
"I'm just happy to have the opportunity to be playing football at a high level, and that's just been my mindset since my career started. And hopefully, more guys take that mindset as opposed to a chip on their shoulder."
The 49ers made Kittle a fifth-round draft pick in 2017, so he has always played for head coach Kyle Shanahan. The tight end believes it was a great situation to be thrown into.
"I mean, it's really fun," Kittle said of playing within Shanahan's offense. "First off, the great thing about tight end [in this offense] is that you get to do everything. I get a run block. I get a pass [protection]. I get to run routes for touchdowns. I get to run the ball in reverses and stuff like that; jet sweeps. So just his creativity and the way he attacks defenses, it's like, different every single week. And it's really fun to be a part of something that kind of changes week to week, and you're not just running your head into a wall, running the same plays over and over and over.
"So the creativity is awesome. The way he uses motions, how he sets it up. We run outside zone like three plays in a row, and even though it's not a good run, he's just setting it up to run a play-action or a bootleg—like a naked bootleg—off of it. It's just fun to be a part of that stuff because if you can do everything in his offense, then the pass game just opens up. If you dominate in the run game, the pass game opens up."
It's tough for Kittle to imagine playing in any other system. He loves Shanahan's creative play designs. Even before the ball is snapped, the motion makes it difficult to determine where the football might end up.
"There's just so much to this offense," Kittle added. "It's just really fun to be a part of it and see how it's evolved over the course of my career. ... Like, one time [WR] Brandon Aiyuk is going to fake down block, and the next play he might actually down block and I'm out and around. And the more you can do that to defenses, man, it's really fun to be a part of."
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