The transfer portal has been a game-changer in college football. This move has helped players get more freedom on a national scale and even help raise their NIL. For schools like Ole Miss, Mississippi State, and Southern Miss, the portal has proven fruitful, yielding some of each program’s top performers in recent years. And there is a big expectation for this cycle, with more than 40 talents announcing their availability. To make things more competitive, the most successful IOL of the Ivy League has made his name available for transfer.

Derek Osman is a 3-star offensive lineman of the Harvard Crimson, from the class of 2022. He is a 6-foot-4, 305-pounder who rarely allows the opponent’s defense to get close to the QB. In the three seasons he played for Harvard, Osman started 17 games and was part of 1,040 snaps, allowing only 1 sack and 1 QB hit. He is in his senior year, with one year of athletic eligibility, and the report suggests he’ll be entering the transfer portal.

According to the College Football Insider, Pete Nakos, Harvard Crimson’s Offensive Lineman Derek Osman, is planning to enter the NCAA transfer portal. On3’s Transfer Portal announced on X, “NEW: Harvard OL Derek Osman plans to enter the NCAA transfer portal, @PeteNakos reports. Preseason All-Ivy League First Team.”

Osman is one of the 45 available athletes in the 2026 NCAA transfer portal. He is rated 89.96%, ranking 14th nationally, and No. 2 in Offensive Tackle. His impressive records with the Crimson make him one of the most-wanted players in the portal. He’ll most likely be available as a graduate, as the Ivy League neither allows redshirting nor athletic participation by graduate students. His non-playing first year makes him available for the transfer.

Based on the NCAA’s single transfer window, the IOL will be available for the programs during the College Football Playoffs, from January 2 to January 16, 2026. Based on the new rules, the players must wait until the second day of the calendar year to enter their names in the portal and contact their target schools. 

Derek Osman’s Career Highlights

Taking a look at Osman’s career, he graduated from Mercer Island High before attending Choate Rosemary Hall, where he played varsity and started all five prep years. He was lined up at every position on the offensive line, and also captained the team, being an academic scholar athlete. 

In 2020, he was named in the All-KingCo selection. Two years later, he became an honoree in the All-Founders League while at Choate Rosemary Hall. He led his school to the NEPSAC title in 2022. Osman started receiving offers from college programs in 2020 and had 16 offers in hand before giving his commitment to Harvard in 2021. Some of the notable offers he received include Syracuse Orange, Princeton Tigers, Notre Dame, Wake Forest, Dartmouth, Yale, Washington, etc.

At Harvard, he is one of the major contributors to the program’s success, and together they built one of the strongest Offensive lines in the Ivy League conference. Since most of the programs are in desperate need of a solid OL like Osman, there are high chances that he lands on a Power 4 conference team.