[5] In his 2015 freshman season, Olszewski was named Northern Sun Intercollegiate Conference (NSIC) Newcomer of the Year.

After the draft, he was invited to participate in rookie minicamps by the Minnesota Vikings, who used him at cornerback,[8] and the New England Patriots, who used him at wide receiver.

[9] On May 23, 2019, after the retirement of Jared Veldheer gave the Patriots a roster opening, they signed Olszewski to an undrafted free agent contract.

[11] On August 31, the day that teams were required to trim their preseason 90-man rosters to 53-man rosters, the Patriots told Olszewski that morning that he would be waived; instead, the Patriots kept him after trading cornerback Keion Crossen less than an hour before the deadline.

[18] A week later, against the Los Angeles Chargers, Olszewski had three punt returns totaling 145 yards.

[26] Olszewski would make his only catch of the 2023 season with the Steelers during Week 2's divisional matchup against the Cleveland Browns.

[30] On October 23, 2023, the New York Giants signed Olszewski to their practice squad, and promoted to the active roster five days later.

[31][32] In Week 17 against the Los Angeles Rams, Olszewski returned a punt 94 yards for a touchdown.

[33] However, research revealed that the record of 95 yards set by Al Bloodgood on September 30, 1928 still stands.