Arsenal were once a massive club in the Premier League but over time their reputation has taken a hit. Especially after Arsene Wenger's retirement, the club has seen a good amount of downfall.With the Gunners failing to qualify for the UEFA Champions League lately, it has been damaging to them in several ways. Not playing in Europe combined with a lack of silverware has hampered their pulling power significantly in the past few years.Arsenal have struggled in the last decadeMany of Arsenal's finest players have opted to leave the club because of their struggles to win trophies. Because of this, the North London club have never been able to fully maintain a squad with their best players.That being said, the Gunners have capitalized decently on when the time has come to sell their players. Without further ado, let's take a look at their most profitable transfers so far.Note: All values are as per Transfermarkt#5 Emmanuel AdebayorWigan Athletic v Arsenal - Premier LeagueMonaco and Arsenal have done quite some business together when it comes to transfers of footballers. One of them was Emmanuel Adebayor when he joined the Premier League club in 2006 for a fee of £9 million.The Togolese striker took some time to settle but once he did, he turned out to be quite productive for the Gunners. In his four seasons with the London club, he scored 46 goals in 104 Premier League appearances. For his impressive performance in 2008, he was named the African Player of the Year.Squawka Football@SquawkaEmmanuel Adebayor is far from happy with his former club, Arsenal. 12:31 PM · Jan 26, 20221788175Emmanuel Adebayor is far from happy with his former club, Arsenal. 😡 https://t.co/63H9sV1HZ7Emmanuel Adebayor decided to join rivals Manchester City in 2009. The transfer fee cost £26.10 million, resulting in a profit of £17.10 million for the Gunners.#4 Marc OvermarsOvermars Scores in the Premier LeagueMarc Overmars was a shrewd signing done under the management of Arsene Wenger. The Dutchman signed for Arsenal from Ajax in the summer of 1997 for a fee of £6.75 million.Overmars received some criticism in his early days but Arsene Wenger played a major role in defending him. The Dutch winger time and again made important contributions in attack. In his 100 Premier League appearances, he contributed 44 goals for the Gunners.Arsenal@Arsenal As it's his birthday...We need to talk about Marc Overmars.What a player 3:42 PM · Mar 29, 20204593611🎈 As it's his birthday...We need to talk about Marc Overmars.What a player 🙌 https://t.co/1qqJTaANaKIn 2000, Barcelona expressed interest in Overmars and the Dutchman equally obliged. The transfer deal cost a fee of £26.37 million, making a profit of £19.62 million for Arsenal.