8. Miami Marlins
Yes, kids, there was a day when the Miami Marlins spent money. They did, however, live to regret it and vowed never to make that mistake again.
Prior to the start of the 2015 season, Marlins owner Jeffrey Loria actually shelled out $325 million over 13 seasons to get the signature of franchise star Giancarlo Stanton on a Miami contract. The deal was severely backloaded; Stanton received only $6.5 million in 2015 and didn’t hit $25 million until 2018.
The deal was also cynical. By the time Stanton did begin to collect the big portion of that contract in 2018, he had been marked for shipment out of town… as it turned out to the Yankees. They inherited the deal Loria had signed in a December 2017 trade.
Still, the Stanton contract is on the books as the richest ever signed by the Marlins both in terms of raw dollar value ($325 million) and AAV ($25 million per season through at least 2027).
Believe it or not, Stanton was actually the second plus-$100 million player signed by Loria. The first was free agent infielder Jose Reyes, who signed with Miami for $106 million spread over six seasons prior to the 2012 season.
That one didn’t work out for Miami, either. Loria bore the cost just one season before including Reyes in a November 2012 12-player swap with Toronto. Reyes lasted just two seasons in Toronto before the Jays unloaded him to Colorado, setting off a hegira that also took him and the deal to the Mets and ultimately back to Colorado.