Montemurro: The art of the big deal: an inside look at the largest free-agent contracts in MLB history

From Meghan Montemurro at The Athletic on November 13, 2018:

Nearly​ 18 years​ ago, Doug Melvin changed the landscape​ in​ professional sports.

Melvin, then​ the general​ manager of the​ Rangers,​ signed​​ 25-year-old shortstop Alex Rodriguez to a 10-year, $252 million contract on Jan. 26, 2001. It smashed baseball’s previous free-agent record signing, set just days earlier by the Rockies and their eight-year, $121 million deal with left-hander Mike Hampton. Rodriguez’s contract became the most expensive ever among U.S. pro athletes, doubling a $126 million deal Kevin Garnett had inked with the Minnesota Timberwolves in 1997.

In the years since, nine Major League Baseball players have signed free-agent deals worth at least $180 million. Bryce Harper and Manny Machado are expected to join that list this offseason; both will likely sign deals exceeding $300 million. As the hot stove season gets underway, The Athletic interviewed six general managers and one team president who had signed eight of the 10 largest free-agent contracts in MLB history, asking the executives to weigh in on the challenges that accompany such deals. Two common themes, in particular, emerged: ownership’s role in the moves and the ripple effects that stem from bringing in an elite player.

“What goes along with that contract, though, is a lot of expectations about the team winning,” Melvin said. “Winning immediately – but there are no guarantees in baseball.”

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Originally published: November 13, 2018. Last Updated: November 13, 2018.