Kristjaan Speakman has earned a reputation as a shrewd operator when it comes to managing player contracts at Sunderland, rarely allowing key talents to slip away without a fight or a plan.
Yet, in the cases of Dan Neil and Dennis Cirkin, it seems two vital pieces of the squad puzzle have momentarily eluded his typically tight grip.
Under Speakman’s stewardship, Sunderland have made it a habit to proactively secure the futures of their standout performers, often extending contracts well before they near their end—sometimes even when years remain on existing deals.
This forward-thinking approach has kept the club from losing prized assets for free or scrambling to offload them in desperation sales. However, a looming challenge awaits in the summer of 2026, when both Neil and Cirkin’s current agreements with the Black Cats are set to expire.
As of this summer, they’ll enter the final 12 months of their contracts, thrusting Speakman into an unfamiliar and somewhat uneasy position.
Despite experiencing occasional dips in form this season, both players remain linchpins for Sunderland. Their importance hasn’t gone unnoticed beyond Wearside either, with Premier League clubs circling.
Transfer insider Graeme Bailey, speaking to Sunderland AFC News, shed light on the situation, noting that Neil and Cirkin are well aware of the external interest in their services. Cirkin has caught the eye of Tottenham Hotspur, among others, while Neil has been on Liverpool’s radar for over a year.
Bailey emphasized that the duo’s hesitation to sign new deals hinges on clarity about Sunderland’s future—specifically, whether the club will be competing in the Premier League or still battling in the Championship next season. Currently, Sunderland sit fourth in the Championship table, a position that keeps promotion firmly in sight but far from guaranteed.
“It’s far from ideal,” Bailey remarked. “They want to understand where the club is headed. Plus, knowing they’ve got suitors elsewhere gives them a sense of their worth, which naturally factors into their thinking.”
Speakman, for his part, has addressed the contract standoff earlier this season, offering reassurance about the players’ dedication to Sunderland’s ambitions—chief among them, a return to the top flight.
“We’ve spoken with them both,” he explained. “There’s no doubt about their loyalty to this club or the project we’re building. That said, right now isn’t the time to dive deep into those discussions.” His stance reflects a calculated choice to prioritize the team’s on-field push over off-field negotiations, at least until the campaign concludes.
For Speakman, the futures of Neil and Cirkin are just two items on a lengthy summer to-do list. With several Sunderland players drawing Premier League attention, the sporting director faces a delicate balancing act come season’s end.
He’ll need to weigh who stays, who departs, and how to reinforce the squad to cover any exits. The uncertainty surrounding Neil and Cirkin only adds complexity to an already high-stakes period ahead for the Black Cats.