MLS Transfer Window Winners: Which Teams Dominated the 2025 Summer Market?

The 2025 MLS Secondary Transfer window could be remembered as one of the most influential periods in league history.
While the 2023 window witnessed Lionel Messi's arrival at Inter Miami, the 2025 edition saw clubs across various market sizes competing for top-tier talent. When the window concluded, multiple star players had joined new teams, with numerous franchises making substantial progress.
Now that the 2025 Secondary Transfer window has ended, Sports Illustrated examines which organizations performed most successfully.
1. FC Cincinnati

FC Cincinnati transformed into legitimate MLS Cup contenders during the recent transfer period, achieving this status despite being among the league's smaller-market franchises.
Although they failed to secure Thomas Müller and saw DeAndre Yedlin depart for Real Salt Lake, their new acquisitions should position them well for a genuine title pursuit throughout the remaining regular season matches.
They reacquired Brenner from Serie A club Udinese on deadline day, forming a dynamic attacking partnership between him and club-record signing Kévin Denkey, supported by playmakers Evander and Pavel Bucha in the midfield.
With Brenner's return, they gain a player who should seamlessly readjust to MLS competition, having netted 27 goals and contributed seven assists across 73 matches for Cincinnati between 2021 and 2023, prior to his Serie A departure.
In additional moves, Dominik Marczuk should integrate smoothly as a wingback after his transfer from Real Salt Lake, while 21-year-olds Samuel Gidi and Ender Echenique possess the potential to contribute meaningfully.
Cincinnati was already among the elite teams, and they've only improved. Given their reliability and fresh talent, they emerge as the leading MLS Cup contenders following the transfer window.
2. Toronto FC

Toronto FC experienced the most transformative window among MLS organizations, successfully escaping the problematic Lorenzo Insigne and Federico Bernardeschi contracts while creating opportunities for their future.
Parting ways with the Italian players through what the organization termed "mutual contract terminations" required significant financial investment. However, this move enabled General Manager Jason Hernandez to begin constructing a competitive roster foundation.
The franchise acted swiftly during the window, investing $8 million plus performance bonuses to acquire attacking midfielder Djordje Mihailović from Colorado Rapids as their central midfield anchor.
Despite the substantial expense, the 26-year-old Mihailović provides ample time to serve as the cornerstone of a rebuilding effort. Subsequently, Toronto added former LAFC standout midfielder Jose Cifuentes on loan from Glasgow Rangers, while trading midfielder Matty Longstaff to obtain young Canadian forward Jules-Anthony Vilsaint from CF Montréal.
While Toronto FC remains distant from MLS Cup contention currently, they've established a solid foundation and could emerge as playoff contenders by 2026.