skip navigation

A brief history of transfers from the USL Championship and League One

By NICHOLAS MURRAY -, 09/21/23, 11:00AM EDT


Milan Iloski’s move FC Nordsjaelland adds to the list of notable moves to top-flight clubs over the past six years

The announcement this past Tuesday that Orange County SC star forward Milan Iloski would be transferred to Danish Superliga club FC Nordsjaelland this January served as the latest major move by a player from the USL Championship to a top-flight club overseas.

These have started to become regular occurrences, of course – this year five players have been transferred from USL Championship and League One clubs to teams in Major League Soccer, while Iloski’s move continues the trend of players moving to top-flight clubs in Europe from the league.

It wasn’t so long ago, however, that those sort of moves just didn’t seem possible, with a paucity of takers in the marketplace for top talents that were competing in the league.

What’s changed? Plenty, for sure, most of all the willingness of USL Championship clubs to invest in players that can not only provide an impact on the field but also have the foresight to find the next step in their pathways, which has led more young talented prospects to turn professional in the USL Championship than ever before.

The league’s visibility and connections in the marketplace have also grown rapidly, both through the league office and front office staff at clubs who have facilitated moves for exciting players eager for their shot at the next level.

Here’s a timeline from the past five years, starting with the move that began a movement, and some of the key transfers that have launched notable careers since.

Mark-Anthony Kaye

Louisville City FC to Los Angeles FC (MLS)
February 5, 2018

Mark-Anthony Kaye lifts the USL Championship Final trophy after his final game at Louisville City FC, prior to a transfer the following offseason to Major League Soccer's Los Angeles FC. | Photo courtesy Em-Dash Photography / Louisville City FC

Mark-Anthony Kaye arrived at Louisville City FC ahead of the 2016 USL Championship season with 30 appearances in the league to his credit, but in need of a fresh start with a path ahead at Toronto FC looking unlikely. In two seasons, Kaye not only became an integral part of LouCity’s first league title winner in 2017, making 49 Championship appearances for the club, but also emerged on the senior national team radar for Canada. Then-MLS expansion side Los Angeles FC was watching and acquired Kaye for the 2018 campaign, and he’s since gone on to make 145 appearances in the top-flight and 40 appearances for Canada, earning a place in the country’s squad for the 2022 FIFA World Cup.

Joseph Okumu

Real Monarchs SLC to IF Elfsborg (Allsvenskan / Sweden)
August 28, 2019

Joseph Okumu might be one of the more remarkable stories in the USL’s history. He received his first international cap for Kenya as a 16-year-old and competed for AFC Ann Arbor after coming to the United States in 2018. After a standout summer in the pre-professional ranks, he signed professionally with Real Monarchs SLC and saw his career start to kick on rapidly. After 13 appearances for the Monarchs, Okumu was sold to IF Elfsborg for a then-USL Championship record fee, where his star has continued to rise. Next was a move to Belgian club KAA Gent, and this past summer he joined Ligue 1 club Stade de Reims. He has currently made a pair of appearances in France’s top-flight in the early going of the campaign.

Tah Anunga

Charleston Battery to Nashville SC (MLS)
January 15, 2020

If Mark-Anthony Kaye was an indication the USL Championship was a place where players could find a new path, Tah Anunga’s move to Nashville SC from the Charleston Battery was sign more clubs from Major League Soccer were seeing value in the marketplace. Anunga was a standout defensive midfielder for the Battery across three seasons and earned All-League First Team honors in 2018 while making 85 appearances overall for the side. Nashville jumped in to make a deal before its inaugural MLS season in 2020 and Anunga remains part of the club to this day, and has made 82 appearances across the regular season and playoffs, serving as a reliable piece in the club’s squad.

Jonathan Gomez

Louisville City FC to Real Sociedad (La Liga)
September 30, 2021

When Jonathan Gomez signed professionally with Louisville City FC in 2020, he wasn’t the first player to join the USL Championship’s ranks from an MLS Academy, but it inarguably marked a sea-change in the way the league was viewed by up-and-coming prospects. Already a known prospect, Gomez emerged as one of the top young players in the United States with LouCity, earning the USL Championship’s Young Player of the Year award and All-League First Team honors in the 2021 season. By that time, Gomez’s move to La Liga’s Real Sociedad had already been announced, and the 20-year-old has since become only the fourth player to appear in a senior international for both the United States and Mexico. Currently continuing his pathway with the current UEFA Champions League side on loan in LaLiga2 with Mirandes, Gomez provided the model other young talents would soon be emulating.

Jose Gallegos

San Antonio FC to SönderjyskE (Superliga / Denmark)
January 28, 2022

From the moment Jose Gallegos showed the step forward he’d taken since being a USL Academy signing in 2019 to preseason in 2020, San Antonio FC signed the talented attacking playmaker to his first professional deal, and set a potentially historic moment in motion. Gallegos played every game of the abbreviated 2020 campaign and then broke through impressively in 2021, earning nomination as a finalist for the Championship’s Young Player of the Year award. After 63 appearances for SAFC over three seasons, he was transferred to then-Superliga club SönderjyskE the following offseason, making him the first USL Academy product to be transferred to a top-flight European club. While the Danish club has since suffered a relegation, the 21-year-old Gallegos remains part of the squad, having recorded eight goals and eight assists in 57 appearances.

Ronaldo Damus

Orange County SC to GIF Sundsvall (Allsvenskan / Sweden)
March 17, 2022

Ronaldo Damus wasn’t the first player to be transferred to Europe by Orange County SC, but his pathway through USL League One to the USL Championship and then to Sweden’s top-flight was the perfect display of the club’s philosophy of developing players while winning on the field. Signed from North Texas SC – where he won the League One title in 2019 while earning the Golden Boot with 16 goals – prior to the 2021 season, Damus led OCSC with 14 regular season goals and then bagged four tallies in the postseason, including two in the Championship Final victory against the Tampa Bay Rowdies to earn MVP honors. That offered a platform for top-flight soccer in Scandinavia, and while GIF Sundsvall’s campaign last year ended in relegation, Damus put up a good account for himself with five goals and two assists. After his loan stint with San Diego Loyal SC comes to an end, the Haiti international will get a chance to see what Europe holds for him again.

Diego Luna

El Paso Locomotive FC to Real Salt Lake (MLS)
June 2, 2022

Signed to his first professional deal as a 17-year-old from the Barca Residency Academy, Diego Luna took little time finding his feet in the USL Championship with El Paso Locomotive FC in the 2021 season. He bagged his first goal in the league in just his fourth appearance and went on to produce a campaign that earned him All-League Second Team honors and nomination for the Young Player of the Year award. Luna’s electric play saw him called up to the United States U-20s that fall, and when he continued to shine for both club and country to start the 2022 season, Real Salt Lake came calling, paying the highest transfer fee received by a USL Championship club from an MLS franchise. After being played cautiously early on by RSL, a breakout display at the 2023 FIFA U-20 World Cup for the United States was followed by a more minutes at the club level, with Luna having now recorded three goals and three assists in 793 minutes this season while being suggested by the likes of ESPN’s Herculez Gomez as a player who should received a U.S. Men’s National Team call-up.

Kobi Henry

Orange County SC to Stade de Reims (Ligue 1)
June 14, 2022

Kobi Henry's transfer from Orange County SC to Ligue 1's Stade de Reims set a then-USL Championship transfer record for the talented young center back.

After Diego Luna’s transfer to Real Salt Lake set a new domestic transfer record for the USL Championship, barely two weeks later Orange County SC’s Kobi Henry smashed the league’s overall transfer record with his move to Ligue 1 club Stade de Reims. Signing with Orange County SC in the 2020 season, the rangy center back competed at the USL Academy Cup in 2021 before thriving in the OCSC lineup as it made its run to the USL Championship title in the fall. Henry’s reputation as a top prospect saw him earn his first call-up alongside Jonathan Gomez in December 2021, and he continued to impress the following year, which saw a deal be struck with SDR, considered one of the top developers of talent in Europe. Henry is now on loan at FC Villefranche-Beaujolais, where he recently made his debut this season, as he continues to build his pathway to the top of the European game.

Hadji Barry

Colorado Springs Switchbacks FC to Future FC (Egyptian Premier League)
October 3, 2022

While the majority of the players transferred overseas are those at the start of their careers, Hadji Barry had built an extensive resume in the USL Championship when the opportunity to join newly-promoted Future FC arrived late in the 2022 season for another USL Championship record fee. A native of Guinea, Barry had shown his qualities at numerous stops, and become the face of the Switchbacks’ resurgence in not only winning the Championship’s Golden Boot in 2021 but equaling the league’s single-season goalscoring record with 25 tallies. Barry’s first season with Future FC saw him notch a goal and assist for his new club as injuries limited his campaign, but with the side finishing third in the league and qualifying for the CAF Confederation Cup, the 30-year-old will look to bounce back upon his return.

Ryen Jiba

Union Omaha to Minnesota United FC (MLS)
January 12, 2023

The Lamar Hunt U.S. Open Cup has been the stage for some remarkable performances and results over the decades, but for Ryen Jiba it provided the platform for a move to top-flight soccer. During Union Omaha’s run to the Quarterfinals of the tournament in 2022, Jiba’s performance in the club’s victory against Minnesota United FC caught the Loons’ attention. After continuing to monitor the South Sudanese midfielder’s play the rest of the season, MNUFC first drafted Jiba’s rights in the MLS SuperDraft last December and then paid a USL League One-record fee to acquire him from Los Buhos. Jiba’s move is one of five transfers between USL Championship and League One teams this year, a new high in the USL’s history, a sign of how the landscape is changing in the domestic transfer market.

Joshua Wynder

Louisville City FC to SL Benfica (Primeira Liga / Portugal)
June 8, 2023

Joshua Wynder's transfer from Louisville City FC to legendary Portuguese club SL Benfica set a USL Championship record, becoming the first seven-figure agreement in league history.

Joshua Wynder story is one that illustrates how far the USL Championship has come in less than a decade. When Louisville City FC launched in 2015, Wynder was there as a fan. Five years later, he was part of the club’s first USL Academy squad that competed at the USL Academy Eastern Conference Regional Event – a precursor to the USL Academy Cup – and in 2021 he made his debut for the First Team in the Championship. Since that appearance, Wynder went from strength to strength, earning his first youth national team call-up in 2022 while being nominated for the USL Championship’s and U.S. Soccer’s Young Player of the Year award at the end of the year. This year he both represented the United States at the FIFA U-20 World Cup in May and earned his first senior United States Men’s National Team call-up before becoming the first USL Championship player to be transferred for a seven-figure fee to Portuguese powerhouse SL Benfica. Earlier this month, the 18-year-old made his debut for Benfica B in the country’s second tier, the start of the next step for Louisville’s hometown prodigy.

Korede Osundina

Orange County SC to Feyenoord (Eredivisie)
August 30, 2023

Korede Osundina’s ascent continued to highlight the pipeline that Orange County SC has developed under President of Soccer Operations and General Manager Oliver Wyss, with the 19-year-old signing professionally with the club from the Barca Residency Academy and making the most of his opportunities for club and country before a major overseas move. Osundina made 37 appearances for OCSC over the past two seasons, appeared for both the United States U-19s and U-20s – serving as a training alternate at this year’s FIFA 2023 U-20 World Cup – and impressed with four goals at a strike rate of a goal every 115.8 minutes this season. Through OCSC’s partnership with Dutch powerhouse Feyenoord – which saw Osundina go on a training stint in the Netherlands last offseason – the 19-year-old is now headed to Europe, with a season-long loan to second-tier club FC Dordrecht the next step in his pathway.

Milan Iloski

Orange County SC to FC Nordsjaelland (Superliga / Denmark)
September 12, 2023

Milan Iloski’s move this week to Danish Superliga power FC Nordsjaelland stands out among the moves that have been made over the past five years and is testament to the visibility the USL Championship now with clubs in Europe. The California native came to Orange County SC after two seasons with Real Salt Lake and has been the most prolific goalscorer in the USL Championship since the start of the 2022 season, recording 34 goals in OCSC’s colors. After claiming the league’s Golden Boot last year, Iloski has continued to shine this year. Combine that level of talent and production with the connections Orange County has overseas and you see a deal that will send the 24-year-old to one of Denmark’s top clubs next January entering the prime of his career having made the most of his chance at consistent minutes in the USL Championship.

“If you're on the field and you're doing well it doesn't really matter if you're in MLS or USL or anywhere else,” Iloski told CBS Sports’ Box 2 Box this week. “It’s just about the quality that you can bring.”

Follow the USL Championship

Most Recent News

Most Read News

Latest Videos