Strachan reckons the Celtic skipper's leadership qualities are essential to transforming his Championship side.
He worked with Scotland star Caldwell Celtic Park when the pair picked up two SPL league titles and led the club to the last 16 in the Champions League.
Caldwell, below, flourished under Strachan at Parkhead and is ready for a return to England where he began his career with Newcastle.
The 27-year-old central defender's current deal with Celtic ends next summer and he wants a big move.
Celtic know they risk losing the player for nothing if he sees out his contract and Tony Mowbray will let him go in January to pick up a fee.
Caldwell, who has 36 caps, can also play in the midfield holding role - another area that has been a cause for concern at Middlesbrough.
The move is key to Strachan's plans to overhaul the club he took over from Gareth Southgate in October. He wants a new emphasis on discipline, fitness and maturity within the Riverside dressing room.
He wants experience and he wants those players on long-term deals. Crucially Boro bosses have not been impressed with the efforts of some of the loan signings that have arrived. Frontman Dave Kitson will return to Stoke City when his short-term spell finishes and Marcus Bent is also likely to be allowed to return to Birmingham.
Strachan only wants players whose full commitment is with the club they are owned by and play for.
He has identified Caldwell as the new leader inside the, club but he also wants two new forwards and a keeper to turn the club's season around and try to get their promotion push back on track.
Strachan wants to build the momentum again following a 3-0 win over Scunthorpe yesterday, and he has been promised significant funds to stamp his own mark on the club.
Strach has made renewed approaches to Birmingham boss Alex McLeish about the possibility of signing veteran hitman Kevin Phillips.
The former Sunderland striker still has a property in the area and is becoming frustrated at his lack of first-team chances at St Andrews.
With financier Carson Yeung set to hand McLeish a major financial boost to put into the Birmingham first team, Phillips' opportunities are certain to recede even further.
McLeish is trying to tie up a mega-deal for striker Kevin Kuryani, with the German international demanding more than £100,000-a-week to move to England.
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