Alan Brazil has told The Sunday Post that he cannot understand why Celtic did not try and sign Jon Flanagan before he moved to Rangers, and suggested that the Gers have taken a risk bringing the right-back to Ibrox.
Flanagan became Steven Gerrard's seventh signing since taking charge of the Light Blues, and he will be hoping to push ahead of either James Tavernier or Declan John in the pecking order at Ibrox having lost his way in recent years.
As well as experiencing some well-publicised off-field issues, Flanagan has gone from being a player who was featuring regularly in a Liverpool side that nearly won the Premier League title to struggling to get a game on loan at Bolton and being released by the Reds at the end of the season.
Rangers have handed him a fresh start with Gerrard a former teammate of the defender, but Brazil has questioned whether he is actually going to prove a good signing given that Brendan Rodgers - who was the manager when Flanagan enjoyed his best year on Merseyside - did not try and bring him to Celtic.
"When I think back to Flanagan’s breakthrough season at Liverpool, it strikes me that Brendan Rodgers was in charge," he told The Sunday Post. "That makes me wonder why, if Flanagan’s as good as Steven Gerrard reckons he is, Brendan has never tried to land him for Celtic?
"I suppose we’ll get an answer to that one in due course. But in the meantime, Flanagan needs to put his past behind him if he hopes to make a success of himself at Rangers. If he can do that – and do the business on the park – Gerrard will be rightly hailed for taking a risk that paid off.
"If he can’t, the Gers gaffer will have to accept the flak that will surely follow."
Celtic do have a handful of right-back options, but it would be little surprise if Rodgers looked to bolster his ranks in that area given that both Mikael Lustig and Cristian Gamboa have looked unconvincing in recent times.
Perhaps, Celtic did register an interest and were just knocked back by Flanagan. But whatever the reason the 25-year-old ended up at Rangers, Gerrard will certainly be hoping that the deal proves to be an inspired gamble that may perhaps leave Rodgers kicking himself for not acting or missing out.