It has been a remarkable career for Milner, and it is far from over yet.
The veteran midfielder has just signed a new one-year contract with Liverpool, committing to his eighth season at Anfield which is, by far and away, the longest he has spent at any club in his senior career.
That senior career began on November 10, 2002, when Milner was a 16-year-old at Leeds, before establishing himself as a first-choice starter in the following campaign of 2003/04.
“When I see him play now, it’s similar to how he was then,” Pennant, who spent three years with Liverpool in the late 2000s, tells This Is Anfield.
“He was never technically amazing, but he was a workhorse, he worked hard. He was good on the ball.
“He wouldn’t be like a Luis Diaz, he wouldn’t take you off your seat. But he was just an all-round good player, and he just stayed on that level all the way through his career
“Obviously being 17, 18 he was a lot quicker, nimble, sharp, eye for goal.
“So I was thinking yeah he’s going to be a great player, a good player.
“I didn’t think for one minute he would last this long, but obviously James never, ever drank, doesn’t drink, so you can see why!”
As Pennant attests, one of the key factors behind Milner’s longevity is his superhuman dedication off the pitch, with the Yorkshireman famously teetotal throughout his career.
At 36, this is probably more widely accepted than back in his teenage years, with Pennant recalling how he and his Leeds team-mates would try to tempt Milner into joining them on nights out.
“I can remember when he was at Leeds, we used to have a Christmas night out with the team,” he recalled.
“Milly would come sometimes with us when he got a bit older, and I used to ask him: ‘Here Milly, taste this’.
“He would say ‘na, I don’t drink’. ‘You’ll like this one, it’s vodka and lemonade, just have a bit of this one’. ‘Na, na, na’.
“He was just adamant while we were all getting blind drunk!”
That is the difference between a player of Milner’s ilk – and there are increasingly few – and a talented player whose top-flight career would have petered out much sooner.
The rewards are an eighth season at Liverpool, and a vital role for one of the best clubs in world football.