The pair previously worked together at West Bromwich Albion.
Di Matteo celebrates winning the FA Cup with Chelsea teammate Marcel Desailly
When fit, the Italian was one of the finest around, treating Chelsea fans for six years with his surging runs and long-range shooting prowess.
As a manager, he's led some of the best: Frank Lampard and Juan Mata at Stamford Bridge; Julian Draxler at Schalke. Even at West Bromwich Albion, his best player was arguably Graham Dorrans; then a young Scottish number 8 who scored 18 goals during a single, promotion-winning, campaign.
Di Matteo with Lampard during his spell at the Blues' interim boss
A reunion between Dorrans and his old boss at Villa Park was recently mooted by us at HITC, but at 29 and having cost around £3 million a year ago, a younger, cheaper option may be sought.
Step forward Romaine Sawyers.
The 24-year-old, who also spent time under Roberto's wing at The Hawthorns, has declined an offer to stay at Villa's neighbours Walsall and is officially a free agent.
Sawyers (L) is unlikely to be short of suitors this summer
Sawyers was still in his teens and largely injured during the 46-year-old's Baggies tenure, but since his release in 2013 he's blossomed into League One's finest attacking mids.
Last season was arguably his best, with six goals and 11 assists arriving en route to the play-offs, where the Saddlers were beaten by Barnsley. Sawyers' impact was duly rewarded though, with a spot in the divisional team of the year.
The Saint Kitts and Nevis international, one suspects, is now bound for the Championship.
Though Walsall to Villa is a sizeable jump, it's certainly been bigger. And it's still nothing compared to the one made by Ashley Westwood four years ago, with five League One appearances to his name.
Westwood was plucked from League One Crewe
Over to you, Bobby.