With that in mind, a question looms: Does Chicago afford to keep both? The answer to that right now is no, as the Bears are currently about $6 million under the salary cap for 2019.
They do have a path to clearing more space. One move would be to release tight end Dion Sims, who had only a small role before landing on injured reserve last season. Parting ways with him would give the Bears about $6 million more in cap space.
The Bears also have the option to restructure some contracts of players who are certain to be part of the 2019 team. Candidates to have their contract restructured to change the accounting of when they receive their money included edge rusher Khalil Mack, cornerback Prince Amukamara and offensive tackle Charles Leno Jr.
But even then, the Bears still may lack the funds needed to bring back both Amos and Callahan. If that's the case, who should they prioritize?
The slot cornerback position is clearly more valuable in today's NFL. That's because top cornerbacks are harder to find, with the skill set for a defensive back to play inside on a slot receiver requiring a specific skill set. Slot cornerbacks must be nifty, quick-footed and explosive with their movements and change of direction to cover the patterns that slot receivers run. A smaller, quicker cornerback often works better in the slot than a taller individual, as they're often asked to cover small receivers.
Callahan has that quickness. At 5-foot-9, he's also a bit small for his position in the minds of some teams. That's part of the reason he went undrafted to start his career.
Callahan's size figures to turn away some teams in free agency, which could depress his value a bit. Because he's viewed solely as a slot cornerback, he won't garner big-money offers.
It would be ridiculous for the Bears to apply the franchise tag to Callahan. We won't know what that 2019 figure is for cornerbacks for another few weeks, but it was $14.975 million in 2018. That range would represent a large overpay for Callahan, as No. 2 cornerback Prince Amukamara carries a $9.5-million cap hit in 2019.
In 2018, the Bears used their sub-package more than 80 percent of the time. Some clubs use such packages around 65 percent of the time. When deciding what Callahan is worth, the Bears need to consider the playing time that slot cornerbacks receive around the league, not just in Chicago.
Because Callahan isn't a true starter, I would think the appropriate salary for him would be what a low-end starting cornerback is receiving around the NFL -- in the $4 million to $6 million range annually.
If the Bears can get a deal done with Callahan in that range, they may have enough cap space to also re-sign Amos, but it won't be easy. Remember, the Bears will probably need to pay All-Pro safety Eddie Jackson significant money after the 2019 season.
Chicago is also planning for the years beyond 2019, and the organization needs to be careful not to put an imbalanced percentage of cap space into a safety position that doesn't carry as much value as other positions.
Finding a starting strong safety should be easier than a starting-caliber cornerback. The Bears themselves symbolize that belief, as both Jackson and Amos were selected on Day 3 of the draft. Rounds three to five should again yield several safeties to be potential NFL starters.
Deon Bush, who replaced an injured Jackson at free safety late last season, is probably better-suited to play the strong safety position that Amos has filled. He would be an in-house candidate if Amos leaves in free agency, as would DeAndre Houston-Carson, who had a strong training camp in 2018 before breaking his arm. He played in 13 games in 2018.
In addition to the respective value of the positions, the Bears' depth at safety could push them toward prioritizing Callahan over Amos if they can't bring both back. That would make good sense.