Chicago Bears fans likely have sympathy with White Sox fans at this point. The long-downtrodden faithful on the South Side appeared to finally have some hope with the constant rumors that their team was the favorite to sign All-Star shortstop Manny Machado in free agency. He looked like a missing piece that could’ve taken their team to the next level.

Time passed. Nothing happened. Finally, the bomb fell that Machado had ended up signing with the San Diego Padres for a reported $300 million. The White Sox quickly stated afterward that they simply couldn’t go that high. Rather surprising given how deep the pockets of their owner are.

Then again the Bears encountered a similar situation not too long ago in 2017. They too were a losing team that needed a bold move in free agency to hopefully jumpstart a turnaround. One position that most felt was crucial was cornerback as it had been a weak point the year before. Soon a big name surfaced among the rumor mill.

Chicago Bears played it cheap on Stephon Gilmore as Sox did with Machado

Stephon Gilmore was coming off a Pro Bowl season for Buffalo at that time. He was young, athletic and a perfect fit for the type of defense the Bears ran. There was even apparent interest from his side in making a deal happen. However, that desire quickly cooled and the rumors vanished. The reason? Gilmore later stated he was disappointed that Chicago wasn’t “more serious” with their offer to him.

He ended up signing with the New England Patriots instead for $65 million over five years. The Bears ended up with Prince Amukamara instead. Gilmore would become a key fixture in the Patriots secondary this past season, earning All-Pro honors and making the interception that all but sealed their sixth Super Bowl championship.

While Amukamara has been a solid addition to the Bears defense, it’s hard not to wonder how different things might’ve been had it been Gilmore instead. He and Kyle Fuller together, both All-Pros in 2018? That would’ve made an already great defense even scarier. Not to mention he’s younger than Amukamara as well.

It’s proof again that sometimes the fear of spending money can be a detriment to a franchise. Sure there will be ill-advised investments at times, but getting great players comes with a high price tag. If you aren’t willing to pay, then they will find somebody who will. It happened with Gilmore and it happened with Machado.