The former Arsenal winger came through in North London at a time when Arsène Wenger’s teams played with freedom, aggression and attacking instinct. He saw first-hand what Arsenal looked like when they played without fear. So when Pennant watches Mikel Arteta’s side in the closing weeks of this season, even while they sit top of the table and prepare for the biggest fortnight in the club’s modern history, he admits the football can be difficult to enjoy.
“Yeah, it can be really, really tough at times,” Pennant told Football Presse.
For Pennant, that is what makes Arsenal’s current situation so fascinating. Here is a side sitting top of the Premier League with two games remaining, still in control of their own destiny, with a home game against Burnley scheduled for Monday before a final-day trip to Crystal Palace. Beyond that, a first-ever Champions League Final appearance awaits against Paris Saint-Germain in Budapest on May 30.
By any objective measure, Arteta has taken Arsenal to another level. But Pennant believes the football itself has changed as the pressure has mounted.
“What we saw at the start, in the middle of the season, it’s just gone kind of backwards,” he told Football Presse on behalf of BetBrain.
“They were cut-throat. They were going forward. They were electric. There was penetration.
“But now, when it’s crunch time and nerves start creeping in, players want to be safe. Players don’t want to make mistakes.”
That caution, Pennant believes, has become obvious in Arsenal’s build-up play.
“I’m seeing far too much that David Raya is one of their players who touches the ball the most in a game,” he said.
“Your goalkeeper shouldn’t be getting that much of the ball.
“What happens? Players go with the easiest option. ‘I’m not going to lose it. I’ll just go back.’ And that’s what we’re seeing now.”
It is not that Pennant doubts Arsenal’s ability to win major trophies. In fact, he still believes their fixture list gives them an advantage over Manchester City in the title race.
“I think Arsenal’s fixtures are more favourable than Manchester City’s,” he said.
“But when you look at how Arsenal are playing currently compared to City… City go into robot mode every year.
“Arsenal are winning, but they’re scraping.”
That was especially evident, Pennant argues, in Arsenal’s recent victory over Newcastle United.
“If they don’t score from that set piece, I didn’t see them scoring,” he said.
“And that’s at home.”
It is a striking assessment of a side that have led the league for much of the campaign, reached Europe’s biggest club final, and stand on the brink of their first league title since 2004.
Yet Pennant believes pressure changes even elite teams.
“When nerves kick in, players stop taking risks,” he said.
“And when that happens… yeah, it becomes a little bit boring.”
Arsenal may be winning. They may even be on the verge of history. But as Pennant sees it, beauty and success do not always travel together in a title race.