Paul Merson says Arsenal must learn their from their mistakes and release striker Alexandre Lacazette at the end of the season - even if he scores 10 goals.
Lacazette's deal with the Gunners expires in June and despite manager Mikel Arteta being keen to keep him in north London, the 30-year-old is holding out for a long-term contract, having opened talks with former club Lyon.
Despite Lacazette's importance to the team at present - filling in as captain since Pierre-Emerick Aubameyang was frozen out and eventually moved on - Merson wants to see the £46.5million signing shipped out.
"If Alexandre Lacazette goes and gets 10 goals before the end of the season, they can't get lazy and just give him a new deal worth £250,000-a-week, thinking it might be his season next season," the Arsenal icon told Sky Sports.
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"For me, Lacazette has had his time at Arsenal. Whatever he does between now and the end of the season, he's had his chance."
The Frenchman is far and away Arteta's most experienced attacker, although the Gunners have been burnt before by handing out lucrative contracts to the likes of Aubameyang and Mesut Ozil when their best years were similarly behind them.
After their form unsurprisingly fell off in the following months, both were released from their eye-watering wage packets, a fate Merson has warned the Emirates hierarchy about.
"What Arsenal now need to start doing is working on not letting happen what has happened too many times in the past when as an Arsenal fan, you are watching these bright young stars in action, and then all of a sudden you see in the press that they've only got a year left on their contracts," the player-turned-pundit added.
"That cannot happen anymore. They've got to keep on topping up players' contracts. They have good young players, and they need to keep on top of their contracts. They can't get lazy and have players run down their contracts and eventually leaving on a free.
"They need to show they have learnt from the mistakes of the past and get these players tied down so that they are playing their best years at Arsenal.
"They have got a good, young squad and if you can add another couple of top-quality signings for next season, I think there are happier times to come for Arsenal. Positive times are around the corner."
Arteta has been coy on the possibility of retaining Lacazette and told reporters in November: "What I can say is I'm really happy with what Laca is doing.
"We're not going to be talking about any of that until the end of the season."
But what could be pushing the Spaniard is Arsenal's lack of striking options, with back-up Eddie Nketiah also set to leave for free in the summer transfer window.
However, Arteta brushed off concerns ahead of the Gunners' trip to Wolverhampton Wanderers in the Premier League on Thursday, having named Lacazette as captain for the rest of the term.
"We have Laca and we have Eddie with us and they are both more than capable of scoring goals and they have shown that over the years with us," he stated.
"Again, when we have to replace or improve the squad, it can only be with a player that we are certain of.
"Fist of all, that they're the right person and the right character to join and then they're a player with the quality to straight away impact the performance of the team and our capacity to build a future around him as well."
