Back in 2012, the defender was proven performer as he preparing to head for the exits at Bolton.
Having established himself as an England international, there was no shortage of suitors for Cahill.
Chelsea eventually won the race for his signature and have seen him go on to make close to 300 appearances for the club while claiming two Premier League titles, the FA Cup, League Cup, Champions League and Europa League.
Arsenal should have been in for his services before he headed to Stamford Bridge, says Smith.
No deal was done then, though, and a former Gunners striker sees no reason why Unai Emery would want to bring in a 33-year-old Cahill during the January window after seeing him slip down the pecking order at Chelsea.
Smith told Express Sport: “Arsenal should have signed Gary Cahill before he went to Chelsea.
“He spoke and had a meeting with Arsene Wenger and it didn’t happen.
“But he went on to become a fine, fine defender.
“Now you’d be signing somebody who’s in his latter years and is not at his peak.
“I don’t see that as a goer.”
While Smith has questioned the merits of making a move for Cahill, the experienced defender is attracting plenty of interest.
He is considered to be a useful short-term option for any number of clubs, with Manchester United credited with holding an interest prior to Jose Mourinho’s departure.
A move away from Stamford Bridge is expected to be made during the winter window, with Cahill struggling for regular game time under Maurizio Sarri and eager to find minutes elsewhere as his contract in west London runs down.