Hayden Hackney has already been the subject of much talk and interest and that will only ramp up in the weeks ahead, with Nottingham Forest and Crystal Palace two clubs strongly linked.
But speculation emerged of interest in another key Boro figure on Tuesday, with West Ham United linked with a move for head of football Kieran Scott.
According to talkSPORT, West Ham are "planning a boardroom restructure" after being relegated from the Premier League for the first time in 14 years and are said to have accepted a new strategy is needed.
The Hammers haven't had a recruitment chief in place since last October and, according to the report, are "showing interest" in Scott.
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And they aren't the first to be linked with the 42-year-old. You might recall that Scott was one of the names mentioned when Crystal Palace were in the market for a new sporting director a year ago and earlier this season reports in East Anglia claimed Norwich City were interested in trying to lure Scott back to Carrow Road, where he'd previously worked as head of recruitment.
None of those links should come as a surprise, for Scott has done a superb job on Teesside since his arrival in September, 2021, and remains a huge asset.
For Scott, like everyone associated with Boro, the aim is to win promotion to the Premier League, and while that hasn't happened on his watch so far, the progress is clear.
In the two seasons prior to his appointment, Boro finished 17th and 10th. Since his arrival five years ago, Boro have made the play-offs twice when, on both occasions they should really have finished in the top two; came up just short twice in finishing seventh and eighth and their lowest finish was 10th, which was deemed a significant disappointment and led to Michael Carrick losing his job for underperforming.
In short, then, Scott has repeatedly assembled squads that have challenged for Championship promotion while also making the club significant sums on several players, who were signed for modest fees and sold on for huge profits: Morgan Rogers, Finn Azaz, Emmanuel Latte Lath and Rav van den Berg.
Boro are still benefiting and will receive a further significant cash boost this summer if Rogers moves on, with Arsenal, Chelsea and Manchester United all interested.
Of course, in an ideal world, those players would have helped to fire Boro to Championship promotion, but trading is of utmost importance.
The most recent accounts, which covered the 2024/25 season, revealed pre-tax losses of £11.4m, but without player sales that figure would have been north of £36m.
That has to be part of the model. And it's not limited to the Championship. As Sunderland's sporting director Florent Ghisolfi explained recently when asked about the prospect of stars leaving the Stadium of Light this summer, clubs can't pitch to players that they can help them take the next step in their career and then block lucrative or dream moves down the line.
Boro obviously want to keep the likes of Adilson Malanda, Aidan Morris and Tommy Conway this summer but all will now have a bigger market value then when they arrived. That's down to good scouting and recruitment.
Of course, there have been misses as well as hits. That's inevitable when you're not forking out eye-watering sums and you're looking for potential in untapped markets. A lot of these players have never played in the Championship before so there's always an element of risk.
But, in the case of Kaly Sene last summer, for example, Boro paid less than £1.5m so the potential reward outweighs the risk, even if it hasn't worked out as hoped with that particular player.
David Strelec was seen as a much safer bet and there's obvious disappointment that the Slovakian international didn't fare better in his first season at the Riverside.
Scott spent much of the most recent January window recovering after being forced to undergo emergency surgery.
Prior to Scott's arrival and during Neil Warnock and Tony Pulis' time in charge, it was clear Boro's transfer strategy was focused around the man in the dugout. There always has to be an element of that, of course, but there was an immediacy to much of Boro's business rather than bigger picture thinking.
But one word that has cropped up again and again in recent years is alignment, which is testament to the work of Scott and head of recruitment Chris Jones.
Last summer, Scott led on the recruitment and appointment of Rob Edwards, and while the head of football never could or would have predicted the head coach walking out after a few months, Middlesbrough made a hefty profit on the 43-year-old, who, while unpopular on Teesside now for obvious reasons, had guided Boro to a record-breaking start.
Scott then managed, with no advance warning - obviously, to go out and lure one of Europe's most highly-rated young coaches to the Riverside.
It should come as no surprise that West Ham have been linked with Scott. It's crucial Boro keep him.