The 10 most significant outbound transfers in Major League Soccer history

Alphonso Davies – Canada – dribbles endline

While the 2019 MLS Secondary Transfer Window is closed, there is still plenty of chatter around players like Aaron Long, Mauro ManotasDiego Rossi and others who could be potential targets of teams in leagues where the window remains open through the end of the month.

With one eye on who may be the next MLS star to test international waters, we focus the other on those who took that jump over the years to evaluate which were the most significant sales in league history.

Several variables weighed in the judging, including size of return, the glamour of the buyer, hurdles cleared in specific markets and how the moved help global perception of MLS. And for transfers done since the beginning of last summer we've included fee figures in both the sum that changed hands at the time (as best gathered from available sources) as well as an adjusted total to 2019 dollars.

Just to set the parameters — we didn't include any free transfers or loans. Even with loads of deals that fit under those categories removed from the equation, there were enough important transfers to choose from to fill two lists. In other words, once we got past the half-dozen or so absolute locks, it was a real bear to pick the few remaining spots and then rank them all.

Before we get to the top 10, let's salute through some of those very honorable mentions: Freddy Adu, Michael Bradley, Clint Dempsey, Maurice Edu, Jack Harrison, Stern John, Brian McBride, Matt Miazga, Chris Richards, Carlos Salcedo and DeAndre Yedlin.

10) Brad Friedel (Liverpool, 1997)

It took English clubs four, count 'em, four tries to grab the big but agile netminder. Before Major League Soccer had ever played a game, Nottingham Forest, Newcastle and Sunderland all agreed deals to sign Brad Friedel in separate transfer windows, only to be thwarted in succession by the notorious UK Home Office work permit approval process.

When big bad Liverpool finally said the magic words at Big Brad's appeal hearing (as he was again rejected by the automatic formula), Columbus Crew SC enjoyed the advantageous timeline to seal a $2.4 million ($4 million in 2019 dollars) sale. The US national team star only hung around MLS long enough to snare a Best Goalkeeper of the Year prize and set the first bar for league out transfers.

9) Andy Najar (Anderlecht, 2013)

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The $3 million ($3.3m adjusted) haul taken in by D.C. United for letting the shifty winger head off to Belgium was decent enough business at the time. And as Belgian clubs go, they don't come any bigger than Anderlecht.

This was also a move that demonstrated to top young players in Concacaf's second pack — Costa Rica, Jamaica, Panamas and Najar's Honduras — that coming to and shining in MLS will draw interest overseas. For added history points, it was also the first time a Homegrown Player was sold for solid coin.

8) Tim Howard (Manchester United, 2003)

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Honestly, considering the time when this happened, the buying club's name alone should put this deal in the top 10. The Red Devils were quite arguably the global brand in soccer back then, and that household name paid a handsome $4 million ($5.6m adjusted) for an American 'keeper out of MLS.

Friedel's move was big and to a big club, but this was on another level at the time and still stands up as a landmark transfer 16 years later. Despite a tough turn in Manchester, Tim Howard went on to carve out an admirable 13-year Premier League career (seventh on the all-time EPL clean sheets chart!) to add a sweet topping.

7) Fredy Montero (Sporting CP, 2013)

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There's encouraging Central American talents to flock to your league, and then there's luring enviable South American assets because they can star for a while and then head to important European clubs. Those are both very good things that happened, but this one was better.

The sale fee collected by the Seattle Sounders from the Portuguese giants was actually a package that included $1.6 million ($1.7m adjusted) on top of the initial $1.2m ($1.3m adjusted) loan fee and undisclosed bonus add-ons. The return fell short of a windfall, but this Fredy Montero tremor started what is now threatening to become an avalanche of top young, marketable Conmebol talents to MLS.

6) DaMarcus Beasley (PSV Eindhoven, 2004)

The end of the first real bidding war for an MLS talent came when PSV Eindhoven doled out $2.5M ($3.4M in 2019 dollars) to the Chicago Fire for DaMarcus Beasley. They beat out rivals Ajax and Southampton, both of whom at one point looked set to land the Fire speedster behind the scenes.

Viewed as a change-up-in-style Arjen Robben replacement, Beasley celebrated two Eredivisie titles while also showing Americans could contribute at the Champions League level. His second season at Phillips Stadion wasn't as fun as the first, but Da Bease remained a sought commodity after leaving.

5) Jermain Defoe (Sunderland, 2015)

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Some transfers are best judged straight up. Others set off a domino effect that adds layers of value. This is one of the latter. And hey, it's not bad on the face of it, either. Toronto FC swapped Jermain Defoe for Jozy Altidore and a respectable bag of money.

Of course, Altidore played a big part in the Reds' treble by bagging many of the 69 goals in 129 total matches he's fired since arriving from a rough Sunderland patch. Just as importantly, the estimated $3.5 million in cash plus salary savings allowed Toronto to then go out and acquire an also-in-his-prime Sebastian Giovinco to act as running mate to the US striker. He, of course, tallied 82 times in 142 contests with the club. If you've not kept score, that makes it a 151-goal, three-title deal.

4) Miguel Almiron (Newcastle, 2019)

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The $24 million rung up in Atlanta was certainly enough make this transfer one of the locks, but there's more to the most recent move listed than income. The stature of the move was at least as important because a famous EPL name splurged for a base fee that was nearly twice as large as the previous record holder.

The prominence of Almiron's Newcastle jump could easily climb or slide in stature depending on how well it ages. Side note: Psst, Steve Bruce, you're using him wrong!

3) Tyler Adams (RB Leipzig, 2019)

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There was a time not so long ago when Bundesliga sporting executives had nearly lost faith in the value of paying for young MLS talent, and American players in particular. That time is now basically over because Adams immediately grabbed a starting (if not starring) role in a side capable of making Champions League noise for the first time.

The $3 million paid upfront didn't shake the transfer world, but the 33% sell-on cut could really pay handsome dividends down the line for the New York Red Bulls. For now, the American, the precocious Homegrown Player will (upon regaining fitness) carry on making other kids back home look more intriguing to top-four German clubs by the RB Leipzig match.

2) Jozy Altidore (Villarreal, 2008)

Eleven summers ago, we were all talking about MLS 2.0 settling in when the big sale fitting of that "generation" arrived. The Red Bulls teen ace smashed the old league transfer record, fetching $10 million ($12m adjusted) from Villarreal.

At the time, the Yellow Submarines were a loaded side with a Champions League semifinal run and a La Liga runners-up finish in their recent history folder. Unfortunately, Altidore was stuck behind a stable of lethal forwards and had to suffer limited playing time with Villarreal and a few tiresome loan spells before providing great value at AZ Alkmaar.

1) Alphonso Davies (Bayern Munich, 2019)

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Off the top, you've got the $13.5 million fee, which is already good for the second most lucrative sale in MLS history even before you tack on as much as another $8.5 million in potential bonuses. The fact it was name-brand giant Bayern Munich shifting those funds to pluck a genuine Homegrown phenom out of MLS adds a whole other layer of awesome.

Digging deeper, the Vancouver Whitecaps' runaway club record sale showed every team in the league the kind of jackpot one could hit by developing academy players. Combine all the factors and you've got the biggest outbound transfer we've seen so far.