Kentucky’s offensive line rebuild is once again front and center this offseason-and that’s becoming a familiar refrain in Lexington. The Wildcats are heading into another winter with major holes to fill in the trenches, and new offensive coordinator Will Stein, along with his staff, is diving headfirst into the transfer portal to find answers.
Let’s be clear: this isn’t a one-off issue. Kentucky has been here before, piecing together offensive lines with short-term fixes.
The portal will be a key tool again this year, and the staff is expected to commit significant NIL and revenue-sharing resources to land plug-and-play starters. But if Kentucky wants to stop this cycle, the long-term solution has to come from high school recruiting and player development.
That process is already underway-and this staff is swinging big.
Just days before the next transfer portal window opens, Kentucky has issued offers to a pair of blue-chip 2027 offensive line prospects, signaling a renewed focus on building from the ground up.
One of those offers went out to Oluwasemilore Olubobola, a rising junior from St. Peter’s Prep in Jersey City, N.J.
Ranked No. 69 nationally in the 2027 Rivals Industry Rankings and the No. 10 offensive tackle in the class, Olubobola is already on the radar of some of college football’s heavyweights. His recruitment includes the likes of Texas A&M, Nebraska, Syracuse, Michigan, and Ohio State.
Kentucky is now throwing its hat into the ring, even as offensive line coach Cutter Leftwich remains tied up with Oregon’s playoff prep. The offer was extended by run game coordinator Derek Warehime, who’s helping spearhead the early stages of Kentucky’s 2027 recruiting board.
Olubobola isn’t the only elite prospect Kentucky is targeting. Jordan Agbanoma, another rising junior, also received an offer.
The Grayson High School (Loganville, Ga.) product is ranked No. 89 overall and is the No. 5 interior offensive line prospect in the 2027 class. His offer list reads like a who's who of SEC powerhouses: Alabama, Auburn, LSU, Georgia, Tennessee, Texas A&M, and Nebraska are all in the mix.
Kentucky is taking a shot in a highly competitive recruitment-and that’s exactly what they need to do if they’re serious about building a sustainable offensive front.
These are long-term plays, sure, but they’re critical. While the portal will likely produce Kentucky’s starting five for 2026, the Wildcats can’t keep leaning on one-year solutions. Developing homegrown talent-guys who can grow in the system, build chemistry over time, and anchor the line for multiple seasons-is the only way to stabilize the position group for good.
The offers to Olubobola and Agbanoma are early steps, but they’re important ones. Kentucky’s staff is doing the groundwork now: building relationships, laying out a vision, and showing top-tier talent that Lexington can be a destination, not just a fallback.
In the short term, the portal will dominate the headlines. But if Kentucky can start stacking wins on the recruiting trail with high school linemen like these two, the long-term outlook for the offensive line starts to look a whole lot brighter.