MLS Offseason's Biggest Steals: Ranking the Five Most Brilliant Signings So Far

The opening month of the MLS offseason is nearly complete. MLS Cup 2025 has become a fading memory, and numerous players from the championship finalists Inter Miami and Vancouver Whitecaps have already secured new destinations.

Although the official FIFA transfer window won't commence until January, MLS's transfer activity is already heating up, with all 30 clubs seeking improvements to position themselves as contenders for the Phillip F. Anschutz trophy in 2026 and beyond.

With December nearly wrapped up, Sports Illustrated presents the top five transfers, both incoming and outgoing, from the MLS offseason so far.

5. Red Bull New York Secure Cade Cowell on Loan Deal

Red Bull New York has experienced an active offseason start, appointing former USMNT midfielder Michael Bradley as head coach and executing eight roster changes under sporting director and ex-Red Bull Julian de Guzman's leadership.

While the club will certainly miss starting keeper Carlos Coronel and crucial center-back Peter Stroud, they moved quickly in attack by acquiring former USMNT youth international Cade Cowell on loan from Liga MX's Chivas de Guadalajara.

The 22-year-old forward spent portions of three campaigns with San Jose Earthquakes, recording 10 goals and 15 assists across 104 regular-season appearances before his Liga MX move, where he has failed to meet expectations with 12 goals and five assists in 69 matches in all competitions.

Returning to MLS, the 2021 MLS All-Star will have an opportunity to rediscover his form and re-enter USMNT consideration.

4. D.C United Land Sean Johnson as Free Agent

D.C. United has undergone a transformative offseason following their last-place MLS finish in 2025 and parting ways with 2024 MLS Golden Boot winner Christian Benteke during roster decisions. Throughout the offseason's opening month, they've strengthened their team's foundation, beginning with the defensive addition of USMNT goalkeeper Sean Johnson as a free agent.

Johnson, 36, delivered an impressive campaign with Toronto FC but struggled to secure victories with a relatively underperforming team ahead of him. Now in his career's twilight, he joins D.C. and should enable the club to grind out results, even when not dominating matches.

Simultaneously, reconstructing the spine has been essential for D.C. United. Beyond Johnson, they acquired center-back Sean Nealis from Red Bull New York for $350,000 in GAM and MLS Golden Boot contender Tai Baribo from Philadelphia Union for up to $4.6 million in a cash-for-player transaction.

3. LA Galaxy Strengthen Defense with Jakob Glesnes, Justin Haak

LA Galaxy endured one of their most disappointing seasons in 2025 and acted swiftly during the offseason to enhance their 2026 prospects, aiming not only to return to MLS Cup playoffs but also to contend for a seventh MLS Cup championship.

During the offseason's first month, they acquired MLS Defender of the Year runner-up Jakob Glesnes from Philadelphia Union for up to $2.2 million GAM, while also signing versatile free agent center-back Justin Haak from New York City FC—another defensive reinforcement move.

Last campaign, Galaxy allowed 66 goals, MLS's second-highest total. Now, Glesnes, who brings 224 MLS appearances, will help anchor their backline alongside Haak, who at 24 already possesses 81 regular-season appearances and an MLS Cup championship.

2. Dayne St. Clair to Inter Miami—Pending Official Confirmation

Multiple reports suggest that 2025 MLS Cup champions Inter Miami will acquire 2025 MLS Goalkeeper of the Year Dayne St. Clair as a free agent.

St. Clair earned the league's premier goalkeeping award with Minnesota United in a campaign featuring a league-best 77.93 save percentage, while achieving career highs with 113 saves and 10 clean sheets across 30 regular-season fixtures.

For Miami, they appear set to upgrade one of their previously weakest areas. While reports suggest their MLS Cup starter Rocco Ríos Novo might return, they clearly identified a gap among their elite players and moved rapidly for the Canadian international goalkeeper, who ranked among MLS's top performers entering free agency.

1. Austin FC Transfer Osman Bukari for $6.5 Million

Austin FC experienced a disappointing 2025, placing sixth in the Western Conference before falling to LAFC in the MLS Cup playoffs' opening round. While losing USMNT striker Brandon Vázquez to injury hindered them, winger Osman Bukari failed to help address their attacking struggles.

Following his May 2024 arrival from Serbia's Red Star Belgrade for a reported $7 million fee, Bukari managed only six goals and 10 assists in 50 appearances across all competitions, never justifying his Designated Player designation.

This offseason, Austin successfully offloaded his $1.5 million contract remarkably well, with Polish top-division club Widzew Łódź paying a reported $6.5 million transfer fee. This financial windfall provides substantial resources to reconstruct their roster throughout the remaining offseason period.