The striker claims he was forced out of St James' Park but Shepherd said: 'I signed Andy as a lad and it's a sad day for Newcastle.
'When I was chairman Liverpool tried to buy Alan Shearer and I refused point blank. It can be done.
Out of Toon: Liverpool Kenny Dalglish proudly presents his club-record signing Andy Carroll
'If Newcastle don't need the money then why sell him? A few weeks ago he signed a new contract and said he wanted to stay with the club forever. They should have said that as he's just signed a new deal he isn't going.
'The trouble these days is money gets in the way of everything.
'Having said that, good luck to Liverpool. They've done a great deal. Andy Carroll will be England's centre-forward for the next 10 years.'
No need: Former chairman Freddy Shepherd things current boss Mike Ashley could have vetoed the sale
Carroll has been a huge hit this season, following on from the key role he played in firing Newcastle back to the Premier League at the first time of asking.
However for every back-page headline he's made, the 22-year-old has made a fair share of appearances on the front, most notably when he was arrested in October following an allegation he assaulted his ex-girlfriend Laurie Henderson, a lingerie model, at her home in Ponteland, Northumberland.
Shepherd, though, is confident Carroll will be able to control his off-field behaviour on Merseyside.
He said: 'He'll sort himself out, he's not stupid, he'll do it. There's no better place to do this than Liverpool.'
Carroll later claimed he had been 'pushed out the door' by the owners who it was alleged assured new boss Alan Pardew that his star man would not be sold.
Editor of the ToonTalk fanzine, Steve Wraith, claimed Carroll had contacted him before flying to Merseyside and said the England striker had been left with no option but to leave.
Wraith claimed Carroll texted: 'I'm gutted to be leaving my home town club, I was told to go. I didn't want to leave that's why I signed a 5 year deal. I was pushed out of the door.'
Protests: Newcastle fans will likely revert to their previous stance on the regime
The deal for Carroll would seem to be excellent business for the club - never before has such a fee, or anything like it, been paid for a player with only 41 Premier League games to his name.
But Newcastle legend Alan Shearer said: 'I think they (fans) will be angry. They don't want to see their top player go. The fans are not really interested in the financial side of things.
'But from the club's point of view, you've got to say that ?35m is just an incredible amount of money. It's only a good deal if they go out and spend ?35m- 40m on replacing him.'
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Explore more:People: Freddy Shepherd, Mike Ashley, Andy Carroll Places: Newcastle, United Kingdom