The 35-year-old has recently been released by Everton, so should the Championship side look to make a move?
With Everton recently confirming that Leon Osman will be leaving Goodison Park this summer after nearly two decades with the Toffees, Garry Monk will surely want to consider making the 35-year-old one of his first signings as Leeds United boss.
In some ways, the move would be an ambitious one. The two-time England international spent 11 seasons as a first-team regular at Goodison Park. And while his opportunities were much more limited this past campaign, his experience will surely ensure that the midfielder has several offers on the table this summer, as some Premier League sides would arguably benefit from having him in their squad.
However, a potential swoop could also be considered a gamble. As mentioned, Osman's performances have not been as strong in recent times, and his age suggests that he may struggle to rediscover anything like his best form.
But Monk may believe that a consistent run of games in the team could help the former Derby County loanee become the kind of player that could lead the Whites towards the promotion picture in the Championship.
With Liam Bridcutt returning to Sunderland at the end of his loan spell, Osman would provide the kind of composure that the Scotland international often displayed during his time at Elland Road. That composure often meant that the unpredictable defence had plenty of support, but also meant that the side were able to build attacks from deep.
And while Monk already has several midfield options to pick from, a short-term deal for Osman would arguably see the likes of Lewis Cook, Alex Mowatt and Luke Murphy have the perfect mentor working with them regularly to help them reach their potential.
His consistency would surely provide the trio with the confidence to play their natural game, safe in the knowledge that they have a reliable presence behind them who is fantastic at reading the game.
And with a player with those attributes being available on a free transfer, a move for Osman may be the kind of calculated risk that helps United make a genuine move towards the top six.