They say you always want what you can’t have—and Jim Harbaugh just proved that on national TV. Sitting across from Rich Eisen, the Chargers head coach cracked a smile, let out a heavy sigh of regret that seemed to fill SoFi Stadium, and then lowered his head. The topic? Colston Loveland. The star he raised in Michigan. The tight end he wanted badly. Real bad. The one who slipped through his fingers like a $100 bill on a windy L.A. day.

Yeah, Jim Harbaugh really wanted Colston Loveland. You could see it in his whole damn body language. On May 2nd, the former Wolverines HC, Jim Harbaugh, hopped onto Rich Eisen’s show and expressed his regret in 100 when Rich Eisen asked, “Colston Loveland was the first tight end taken in the NFL Draft this year, right? And there’s a lot of Bears—I’m serious—listen, Tyler Warren is a very talented kid, and Penn State fans have seen that firsthand. I’m getting a lot of Bears fans going, because they ask me—they come to me as the Michigan guy. They’re like, ‘Did we take the right guy in Colston Loveland?’ And I know again, you weren’t drafting that high, but you’re smiling—the Bears taking Colston Loveland—what can you tell Bears fans about this kid, Jim?”

Jim Harbaugh let his sorrow fly. “Yeah, I can compare him—Tyler Warren’s a great player, Colston’s a great player—but they are going to absolutely love Colston Loveland. And as much as I would have loved to have seen him on the Chargers—because, it’s like, you know, there’s 256 players drafted, you know, we have nine picks—the odds are, every single one of these guys is going to be playing against us, you know? But we got our nine. We love ’em,” he trailed off, practically groaning in pain. Let’s keep it a buck—if Colston was on the board when L.A. picked? That draft card would’ve been in faster than a Tesla in sport mode.

But nope. Chicago said, Nah, we need that. The Bears snatched Loveland at No. 10 overall and left Harbaugh wondering what could’ve been. And just like that, the Chargers were back in the lab with nine picks and a whole lot of dreams. They walked away with solid talent like WR Tre Harris and RB Omarion Hampton, but that TE spot? Yeah… that gap is still gaping like a pothole on the 405.

Why all the noise over Colston Loveland, though? Simple. He’s low-key built for this system. Big hands. Precise routes. A straight-up nightmare in the middle of the field. 56 catches, 582 yards, and five tuddies in 2024 alone. That isn’t any scrub resume. He had defenses looking like they were trying to catch ghosts in daylight. And here’s the kicker: he already thrived in Harbaugh’s pro-style offense in college—the exact system L.A. is trying to run in the league.

Let’s not forget, the Chargers’ tight end room isn’t exactly crowded with killers. Will Dissly? Homie dropped two crucial passes in that Wild Card L to Houston. Herbert’s out here needing a safety blanket, and Loveland was that guy. Would’ve been the perfect middle-field bully to pair with Ladd McConkey and Quentin Johnston. But again, what-ifs don’t win you games.

The Bears, on the other hand, saw the vision. While folks were hyping up Tyler Warren, Chicago said, Forget the headlines—give us the fit. “We just felt that the alignment from coaching, scouting, everybody that touched both players that [Loveland] was the best fit for us,” said Jeff King, the Bears’ senior director of player personnel. Even Ben Johnson saw that LaPorta DNA in Loveland. And with Caleb Williams needing a go-to dawg? Loveland just might be his Cole Kmet complement.

Jim Harbaugh sends 6-word message to Wolverine Nation

Jim Harbaugh might be rocking powder blue now, but trust—his blood still bleeds maize and blue. After the 2025 NFL Draft saw THREE of his old Michigan boys go in the first round, Harbaugh hit Wolverine Nation with a humble flex. Six words: “Just awfully, awfully proud of them.” And honestly, he should be proud.

Mason Graham went fifth to Cleveland. Colston Loveland, No. 10 to the Bears. Kenneth Grant? Scooped by Miami at 13. That trio tied a Michigan record set way back in 1995 and again in 2001. That’s rare air. Back then, it was names like Ty Law, Trezelle Jenkins, and Steve Hutchinson. Legends. Now, Harbaugh’s era got names to match. In a pre-draft chat with Yahoo, Harbaugh called his former players “beloved sons.” He said, “You look at the players, and it’s like, you get one pick every 32 picks… most likely, you’ll be playing against them.” And look at that—he isn’t lying. Every one of them might end up coming for his neck on Sundays.

But that’s the NFL. You raise them, groom them, and then the league drafts them away to potentially smoke your defense next fall. The Chargers’ pick at No. 22 was Omarion Hampton, and he’s going to pair with Najee Harris to give Herbert a strong running duo. Still, you can feel the “damn” in Harbaugh’s voice whenever Loveland’s name comes up.

That draft just solidified what Harbaugh did in Ann Arbor. Seven straight years with a Michigan player in the first round? That’s crazy development. That’s turning boys into ballers. Now, imagine Loveland doing what LaPorta did in Detroit last year. He got that same feel. Tight hips, clean breaks, sticky hands, and a football IQ that’ll age like fine wine. Chicago might’ve finessed the rest of the league on this one.

Harbaugh knew. You could see it in how he cringed when Rich Eisen brought it up. That was the sigh of a coach who could already see Loveland on the opposing sideline, torching his linebackers on a seam route. But hey—that’s how the cookie crumbles. Or maybe how the tight end runs right past your zone D. Either way, Harbaugh’s got his squad. He isn’t crying. But he damn sure isn’t forgetting either.