# Best Premier League Transfers? Groß, Caicedo, Grealish and Torres on 8 Lists
> Brighton paid £4m for Caicedo; Chelsea paid £115m. Premier League transfers on 8 lists: Brighton bargains, British records, flops, players sold too soon.
*By YPB Team · Published October 7, 2026 · https://youpick.best/articles/premier-league-transfers-ranked-many-ways*
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The Amex at Falmer, home of the club that sold two of Chelsea's best signings of the decade. Photo: Barbara van Cleve, CC BY-SA 4.0, via Wikimedia Commons.
Pascal Groß was the Premier League's Player of the Month for September 2026. At 35 he is the first Brighton & Hove Albion player to win the award, and the sixth-oldest winner of it.1 Brighton have bought him twice, in 2017 and again in January 2026.
That makes Groß a fair place to start on Premier League transfers. Eight YouPickBest rankings sort them by different rules: the best buys of one club, the best buys of another, the signings called overrated, the players sold too soon, the fees that left England and the outright flops.
> Two of Chelsea's best signings of the 2020s came from Brighton, and three of the British record fees on these lists were paid by Chelsea.
## Pascal Groß vs Kaoru Mitoma: Brighton's best signing, twice
The 21 Best Brighton & Hove Albion Signings of All Time runs from Peter Ward, signed from non-league Burton Albion in 1975, to João Pedro, who left for Chelsea in 2025.
Groß was the club's first purchase after promotion to the top flight, a £3m signing from Ingolstadt in 2017. Brighton sold him to Dortmund in 2024 and paid £1.2m to bring him back eighteen months later.2 "There were a couple of other options, but Brighton was always the priority," he told Sky Sports on his return.
Kaoru Mitoma has the other kind of case. Brighton signed him from Kawasaki Frontale in 2021 and sent him straight to Union Saint-Gilloise in Belgium for a year. In January 2023 his 91st-minute goal knocked the holders Liverpool out of the FA Cup.
The list also holds the players Brighton sold at a profit: Moisés Caicedo, Alexis Mac Allister, Marc Cucurella, Leandro Trossard, Carlos Baleba. A signing can be judged by what he did at the Amex or by what he fetched on the way out, and the two answers rarely match.
A German midfielder bought twice against a Japanese winger loaned out first. Play it →
## Enzo Fernández vs Moisés Caicedo: two British records in seven months
The 18 Greatest Chelsea Signings of the 2020s includes two players bought from Brighton, Caicedo and Cucurella, alongside Cole Palmer and Thiago Silva.
Enzo Fernández came first. Chelsea paid £106.8m to Benfica in January 2023, a British record, weeks after he won the World Cup with Argentina.3
Caicedo broke that record in August of the same year. Chelsea agreed an initial £100m plus £15m in performance-related add-ons, a total that eclipsed the fee for Fernández.3 Brighton had signed Caicedo from Independiente del Valle in Ecuador for £4m in 2021.4
Price is only one way to read this list. Thiago Silva joined from Paris Saint-Germain on a free transfer in 2020 and won the Champions League with Chelsea the next spring. Cole Palmer arrived from Manchester City in 2023 without a record fee attached and was named the PFA Young Player of the Year a season later. Both have a claim against the two most expensive midfielders in the club's history.
Two midfielders, two record fees, one year. Play it →
## Marc Cucurella vs Jack Grealish: what "overrated" costs
The 9 Most Overrated Big-Money Transfers of the 2020s judges price tags: Antony, Romelu Lukaku, Mykhailo Mudryk, Kalvin Phillips, Grealish and Cucurella.
Cucurella spent one season at Brighton. Chelsea paid a guaranteed £55m and up to £7m in add-ons for him in August 2022. Graham Potter, then Brighton's head coach, said the defender "wanted the opportunity of playing Champions League football with a view to accelerating his progress to Spain's World Cup squad."5
Grealish set the record that Chelsea later broke twice. Manchester City paid Aston Villa £100m on 5 August 2021.6
Both men have a reply to the label. Cucurella won Euro 2024 with Spain at left-back. Grealish won the Premier League, the FA Cup and the Champions League with City in 2023. The list weighs a first impression against a fee, and both first impressions have aged.
A Brighton full-back and a Villa captain, both called overrated, both with medals since. Play it →
## How Manchester City buy: Rodri and Erling Haaland
The 14 Best Manchester City Signings of the Guardiola Era is a list of finished players. City bought Rodri from Atlético Madrid in 2019, Haaland from Borussia Dortmund in 2022, Rúben Dias from Benfica and Bernardo Silva from Monaco.
Rodri won the 2024 Ballon d'Or, the first player at a Premier League club to take it since Cristiano Ronaldo at Manchester United in 2008.7
Rodri also scored the only goal of the 2023 Champions League final against Inter in Istanbul, the night City completed a treble.
Haaland's case is goals. He broke the Premier League's single-season scoring record in his first year in England, and Rúben Dias had already been named the Football Writers' Footballer of the Year in his own first season.
City's best buys on this list were already internationals when they arrived. The question here is which established star improved the team most, and price barely enters it.
The record-breaking striker against the Ballon d'Or midfielder. Play it →
## Mohamed Salah vs Kevin De Bruyne: the two Chelsea let go
The 13 Best Players Chelsea Sold Too Soon includes Salah, De Bruyne, Declan Rice, Antonio Rüdiger, Fikayo Tomori and Marc Guéhi, enough for most of a Premier League back line and midfield.
De Bruyne barely played at Stamford Bridge and was sold to Wolfsburg in January 2014. He was the Bundesliga's player of the year at Wolfsburg in 2015, and Manchester City brought him back to England that summer.
Salah followed a similar route. Chelsea bought him from Basel in 2014, loaned him to Fiorentina and sold him to Roma, and Liverpool signed him in 2017. He won the Champions League in 2019 and the Premier League in 2020 at Anfield, two trophies he never won at Chelsea.
Declan Rice left Chelsea's academy as a teenager, grew up at West Ham and joined Arsenal in 2023, the summer Chelsea paid a record fee for Caicedo.
Two players Chelsea owned before anyone knew what they would become. Play it →
## Written off at first: Van Dijk at Liverpool, Modrić at Madrid
The ranking of star signings unfairly written off at first collects players whose fees looked wrong for a season: Thierry Henry, Dennis Bergkamp, Didier Drogba, David de Gea, Rodri.
Liverpool paid Southampton £75m for Virgil van Dijk in December 2017. It was a world record for a defender, well above the £54m Manchester City had paid for Kyle Walker months earlier.8 Southampton sold Van Dijk the way Brighton would later sell Caicedo: bought from a smaller league, developed, sold to a club with Champions League money. Liverpool's 2019 European Cup and their first league title in thirty years both came with him at centre-back.
Luka Modrić left the Premier League for Real Madrid in 2012 for £30m. By that Christmas, Marca readers had named him the worst signing of the summer, with 32% of the vote.9 He won the Ballon d'Or in 2018.
Spurs' midfielder in Madrid against Southampton's centre-back at Anfield. Play it →
## £142m out of Anfield: Coutinho, Ronaldo and the fees that left England
The 13 Biggest Player Transfers in Sports History mixes football with American sport: Babe Ruth's sale to the Yankees, Gretzky's trade to Los Angeles, the Herschel Walker deal in the NFL, Neymar's move to Paris.
Two of the football entries left the Premier League. Cristiano Ronaldo moved from Manchester United to Real Madrid in 2009 for a world-record fee, a year after winning the Ballon d'Or as a United player. Six years at Old Trafford had turned a teenager from Sporting into the most expensive footballer alive.
Philippe Coutinho left Liverpool for Barcelona in January 2018 in a deal worth £142m, with £105m paid up front, itself a British record for a sale.10 Liverpool had signed him from Inter in January 2013. The sale was agreed days after Van Dijk arrived at Anfield, so one January window both bought the world's most expensive defender and sold one of the most expensive midfielders.
Neymar's move from Barcelona to Paris Saint-Germain in 2017 remains the most expensive transfer in football, and it never touched England.
Two Premier League exits that set the market. Play it →
## Fernando Torres vs Antony: when the fee became the story
This ranking of Premier League transfer flops covers three decades of disappointment, from Andriy Shevchenko and Ángel Di María to Jadon Sancho, Timo Werner and Antony.
Chelsea signed Torres from Liverpool on 31 January 2011 for a British record of around £50m.11 Liverpool spent part of it the same evening on Andy Carroll, and Carroll is on this list too.
Antony cost Manchester United a fee that put him among the most expensive signings in the club's history when he arrived from Ajax in 2022. His Premier League output never caught up with the price.
Torres has the strongest defence of anyone here. He scored the goal at the Camp Nou that sent Chelsea to the 2012 Champions League final and won that trophy and the Europa League in a Chelsea shirt. A flop with two European medals is still a flop by the measure this list uses, which is the fee.
A Champions League winner and a winger from Ajax, judged against their price. Play it →
## Brighton's shop, Chelsea's till
Players found cheaply by Brighton and Southampton were sold to Chelsea and Liverpool at record prices; Manchester City paid theirs for players who were already stars. Groß against Caicedo comes down to football played against money made, and each ranking here is [ordered by pairwise picks](/articles/how-head-to-head-voting-works), so a reader decides which of the two counts.
Fans of any club know a bargain their side signed that no record fee has matched. That list is theirs to build.
## More rankings, more angles
- [Where Does De Bruyne Rank in Premier League History? 14 Lists](/articles/how-many-ways-to-rank-kevin-de-bruyne) — Chelsea's reject, City's playmaker
- [Rodri: Best Defensive Midfielder of All Time? 14 Lists](/articles/where-does-rodri-actually-rank) — the Ballon d'Or holding midfielder
- [Where Does Álvaro Morata Rank Among Spain's Strikers? 13 Lists](/articles/alvaro-morata-ranked-many-ways) — a striker who kept going home
Sources
Sports Illustrated — Premier League Player and Manager of the Month for September 2026: Pascal Groß, 35, the first Brighton player to win the award and the sixth-oldest winner: si.com (checked 2026-10-07)
Sky Sports — Pascal Groß interview on his return to Brighton: the £3m signing from Ingolstadt in 2017, the £1.2m fee paid to Borussia Dortmund in 2026, and his quote: skysports.com (checked 2026-10-07)
Sky Sports — Chelsea sign Moisés Caicedo: an initial £100m plus £15m in add-ons, eclipsing the £106.8m British record paid for Enzo Fernández in January 2023: skysports.com (checked 2026-10-07)
theScore (Reuters) — Brighton signed Caicedo from Independiente del Valle for £4m in 2021: thescore.com (checked 2026-10-07)
The Irish Times — Marc Cucurella moves from Brighton to Chelsea: a guaranteed £55m plus up to £7m in add-ons, and Graham Potter's statement: irishtimes.com (checked 2026-10-07)
ESPN — Manchester City sign Jack Grealish from Aston Villa for a British record £100m, 5 August 2021: espn.com (checked 2026-10-07)
Premier League — Rodri wins the 2024 Ballon d'Or, the first Premier League player to do so since Cristiano Ronaldo in 2008: premierleague.com (checked 2026-10-07)
Liverpool FC — Liverpool agree a world-record £75m fee for Virgil van Dijk; the previous record for a defender was £54m for Kyle Walker: liverpoolfc.com (checked 2026-10-07)
Planet Football — Luka Modrić voted the worst signing of the season in a Marca poll with 32% of the vote, after a £30m move from Tottenham: planetfootball.com (checked 2026-10-07)
BBC Sport report, republished by Graphic Online — Barcelona sign Philippe Coutinho in a £142m deal, £105m up front, a British record: graphiconline.com (checked 2026-10-07)
Sports Illustrated — Chelsea agree a British record fee of around £50m with Liverpool for Fernando Torres, 31 January 2011: si.com (checked 2026-10-07)
