Bears Sign Holy Cross Alum Kalif Raymond to One-Year, $5.1 Million Deal

Kalif Raymond is heading to Chicago, reuniting with the coaching staff that helped define his career. The wide receiver and return specialist agreed to a one-year contract worth $5.1 million with the Chicago Bears, per ESPN's Jeremy Fowler, with NFL Network reporting the contract value. The deal brings Raymond back together with Bears head coach Ben Johnson, who served as Detroit's offensive coordinator from 2022 through 2024, and wide receivers coach Antwan Randle-El, who held the same position with the Lions before both made the move to Chicago last year.

Raymond spent the past five seasons in Detroit after the Lions signed him as an unrestricted free agent in March 2021. Over that stretch, he accumulated 171 catches for 2,185 yards and seven receiving touchdowns while becoming one of the most dangerous returners in the league. He scored three punt return touchdowns as a Lion and, in 2025, set the franchise record for career punt return yards with 1,485. He was named a second-team All-Pro as a punt returner in both 2022 and 2024, and led the entire NFL in punt return yards in 2024 with 413. His 2025 season produced 24 receptions for 289 yards and a touchdown across 15 games.

The path to that production was anything but straightforward. Raymond entered the league as an undrafted free agent out of Holy Cross in 2016, latching onto the Denver Broncos' practice squad before being waived on September 2, 2017, and claimed by the New York Jets the very next day. He subsequently played for the New York Giants and the Tennessee Titans before landing in Detroit.

The Holy Cross chapter of Raymond's story is where the underdog narrative begins. A 5-8 receiver from a small Jesuit school in Worcester, Massachusetts, Raymond sent out roughly 800 emails to college programs and heard back from fewer than 10, some of those responses automated. Lehigh and Holy Cross were the only programs with any interest, and both worried about a shattered ankle Raymond had suffered. He rehabbed in time to run track the following spring and, on a visit to the Holy Cross campus, wore three pairs of socks, large boots, a hoodie, his letterman jacket, and baggy pants in an attempt to look taller. Head coach Tom Gilmore extended a scholarship offer on Signing Day, Raymond being the last recruit called into the office that night.

Raymond endured three or four surgeries during his senior year at Holy Cross, all the result of over-training, according to a Golongtd profile of Raymond. He still produced 978 receiving yards and nine touchdowns that season, enough to earn that practice squad spot in Denver.

The psychological toll of early NFL life was equally steep. After never muffing a punt at any level of football, Raymond dropped one in practice ahead of the Jets' season opener against the Buffalo Bills. "The muff changed him," as the Golongtd profile put it. "The muff served as a sucker punch to all of the confidence he had built up." What followed was a decade-long process of rebuilding, grinding through roster cuts and team changes before the Lions gave him stability and Johnson's offense gave him purpose.

Now, with Johnson running his own program in Chicago, Raymond arrives as both a proven offensive weapon and a special teams asset with an All-Pro pedigree, the kind of dual-threat value that fits naturally into what the Bears are building.