Fans questioned the judgment of manager Walter Smith as he shelled out more than £2million to bring him to Ibrox from Wigan Athletic.
Five years on, the club and the Ibrox legions have more than had their money's worth from the versatile star.
And Sunday's Irn-Bru Third Division fixture against Elgin City was undoubtedly one of the highlights for the 34-year-old.
McCulloch may be in the twilight of his career, but his importance to the Rangers cause is greater now than ever, with supporters taking him to their hearts like never before as he leads by example through Rangers' darkest hours.
The departure of Carlos Bocanegra on transfer deadline day left manager Ally McCoist searching for a new skipper.
In truth, McCulloch was the only candidate in town.
As he wheeled away in celebration after scoring on Sunday, his passion for the club was clear to see as he kissed the armband in front of his adoring public.
It was a moment to savour for the Gers veteran and one of his former mentors at his first club Motherwell, Pat Nevin, is delighted to see him finally given the ultimate honour.
"Lee is the perfect man for the job," Nevin told SportTimes.
"Like everyone, you mature as you get older and get more experienced.
"He is a good leader, he is a good laugh and he is a really likeable character. He has all the qualities you want in a skipper.
"You need to be a lot of things to take on that role successfully. He will have the respect of the dressing-room and he is liked by the fans.
"It is perhaps a surprise that he has not been a captain earlier than now. He has not really had the opportunity that much, but his time has come now and it is thoroughly deserved."
Nevin saw at close hand McCulloch's aptitude for the game when he moved to Fir Park in 1998, where he spent two years at the end of his own glittering professional career.
His promise was soon spotted by Wigan, with the £700,000 splashed out by the Latics to make the Scot their record purchase a signal of their trust in his abilities.
It is at Ibrox where McCulloch has flourished, however, as he has helped the Gers to eight domestic honours and to the Uefa Cup Final in Manchester four years ago.
Many have questioned his attributes and worthiness of a place at the heart of Rangers' plans since his arrival in Glasgow, but Nevin reckons it is McCulloch's hunger for success that has lead him to significant on-field glory.
"When Lee started out at Motherwell, he had such a desire to maximise his ability and his potential," he said. "He came through just before guys like James McFadden and Stephen Pearson and with guys like Stevie Hammell so there were a lot of good young players at the club and in the ranks at that time.
"Lee was determined to make the most of his career.
"He obviously had the physique and the athleticism but it is his mentality that sets him apart. You have to work for any success you get and Lee has made the most of his career.
"He has played at the top level in England, he has played for Scotland and he has played in Europe and won things in Scotland with Rangers.
"He has managed to do it all playing in a number of positions as well.
"Central midfield was always his preferred position, but he has been very good on the left wing and now you can see him playing well up front for Rangers."
Sunday's 5-1 defeat of Elgin proved significant in many ways for McCulloch, with his delight at the triumph that kept up Rangers' unbeaten start to the season surely only matched by the pride at his part in proceedings.
He lead from the front as he bagged two goals to notch the 100th and 101st strikes of his professional career as he continues to break down barriers and set standards in his 16th season in the game.
Nevin said: "I think Billy Davies was the first one to spot Lee's ability as a striker at Motherwell. Lee saw himself as a central midfield player and not a striker.
"When he was asked to play up front, he said he would but he made it clear we shouldn't expect much from him. He always had a natural eye for goal.
"You would see him in training scoring goals from long range and scoring 25-yarders regularly.
"If you can do it from that far then we knew he could do it from closer range.
"He was good in the air as well, which helped, and he has proven how good an option he can be up front already this season."