Aston Villa are pushing for a permanent sale of the 28-year-old Jamaica international, who has just a year left on his contract, while Hull have favoured a loan given the financial complexity of his situation; talks remain ongoing over the eventual structure.
Bailey joined Villa from Bayer Leverkusen for around £25-30m in 2021, going on to make 163 appearances, but has fallen down the pecking order under Unai Emery after a difficult loan spell at Roma was cut short in January. Hull have already made four signings this summer, including goalkeeper Jack Butland and defender Matt Targett, and see a move for Bailey as the marquee addition to their attack ahead of a first Premier League campaign in several years.
Elsewhere at the MKM Stadium, 18-year-old winger Ramell Carter has joined National League side Worthing on loan until January 2027. Signed from Tottenham at Under-16 level in 2024, Carter was a regular for Hull's Under-18s and Under-21s, scoring his first Under-21s goal against Crewe Alexandra in October 2025 before signing his first professional contract, a two-and-a-half-year deal, in February. He was part of the Under-18 side that reached the national Professional Development League play-offs for the first time and was named among the substitutes for the first team in last year's Raich Carter Trophy fixture against Sunderland.
Carter joins a Worthing side who won the National League South title last season and will play in the fifth tier for the first time in their 140-year history under manager Adam Hinshelwood, with a debut possible in their season opener away at Carlisle United on 8 August.
Hull City have also tied down five members of that same record-breaking Under-18 group to their first professional deals: defenders Charlie Leach and Calvin Okike, midfielders Reuben Silk and Alfie Maskell, and forward Zac Jagielka, all of whom will move up to Conor Sellars' Under-21 squad for 2026/27.
Okike, the Frank Donoghue Academy Player of the Year, has signed a two-year deal with a club option for a third, while Leach, Silk and Jagielka have signed one-year deals with a similar option and Maskell has put pen to paper on a six-month contract as he continues his recovery from a long-term injury.
Jagielka, a Wales youth international who joined from Liverpool, was a prolific scorer for the Under-18s and spent time on loan at Stocksbridge Park Steels, while vice-captain Leach also featured for the Under-21s in the Premier League Cup against Reading and Bournemouth.
Okike scored within a minute of his senior debut on loan at Hartlepool and was named among the Hull first-team substitutes for the win at Norwich last November, and Silk set up the Under-18s' semi-final goal in their run to the national play-offs.