But there was another NFC North team in the mix for Montgomery's service.
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"The Bears, the Detroit Lions (where he landed) and Minnesota Vikings were all in the mix," Brad Biggs wrote in a mailbag for the Chicago Tribune.
Biggs notes the Lions' deal offered more guaranteed money than the Bears, specifically guaranteed money beyond the first year of the deal.
General manager Ryan Poles believes Montgomery will have extra motivation heading into next season.
"He definitely is going to run with a chip on his shoulder, so we’ll be ready for that," Poles said.
Poles also noted that players have choices and Montgomery made his, and clearly he had a lot of choices within the division alone.
But Poles doesn't necessarily have any regrets about his attempt to re-sign Montgomery.
"I thought we communicated well, I thought we negotiated well," Poles said. "At the same time, you don’t always know what’s going on in the background, but I thought we did a good job, we were transparent, we were organized and it just, it didn’t happen."
Montgomery spent four seasons in Chicago, racking up over 3,600 rushing yards and 26 touchdowns. He became a fan-favorite during his time, known for his violent and persistent rushing style. During his final season in college, he led the NCAA in broken tackles.
The Bears reacted quickly and signed Travis Homer. Homer is a veteran backup who spent the last four seasons with the Seattle Seahawks.
Then a couple of days later the Bears signed D'Onta Foreman as well. Foreman took over Christian McCaffrey's post when the Panthers dealt him to the San Francisco 49ers in the middle of last season.
Throughout last season, Foreman rushed for 914 yards and four touchdowns, despite playing in 35 percent of offensive snaps over the season. Foreman said he plans to vie for the starting running back spot with the Bears.
Foreman will likely split time with Khalil Herbert, who posted an outstanding sophomore season alongside Montgomery last year. Trestan Ebner is also in the Bears' running back room.