History tells us why megadeals matter

November 15th, 2019

Brian Cashman, the Yankees general manager, suggested after his team lost to the Astros in the American League Championship Series, that the Yankees might have been just one or two plays away from going to the World Series, and maybe winning their first pennant in 10 years. You know why Cashman said that? Because the Yankees were one or two plays away from beating the Astros.

But in response to that the other day at the General Managers Meetings in Arizona, Scott Boras -- an agent impersonating a general manager -- said this:

“Let’s see. I watched the Astros series. I kind of watched a player in particular games make them more than one play away.”

Boras was talking about his guy, Gerrit Cole, who is a free agent now and is going to get paid, probably with the biggest free agent contract any pitcher has ever gotten, whether the Yankees are serious bidders for his services or not. But of course Boras knows from past experience -- his own -- that the price always goes up when the Yankees are at the table, even if they haven’t been spending lately on free agents the way they used to.

What Boras is really suggesting here, with the subtlety of a sledgehammer as usual, is that while the Yankees might not have been one or two plays away in his opinion, they were one player away: Cole. One of his guys. And what Boras really touched on here is why contending teams are willing to spend, and spend big, every single baseball winter, for star players like Cole, or Stephen Strasburg and Anthony Rendon, who also happen to be Boras clients:

Because owners and general managers often believe, deeply, that they are one player away.

And guess what?

They often are.

Here are the 10 biggest baseball free agent contracts in history, unless somebody has signed a bigger one since you started reading this:

  1. Bryce Harper, Phillies, 13 years, $330 million (2019-31): Boras and Bryce were looking to break a record, they did, until Mike Trout got more from the Angels, even though he wasn’t a free agent when he did.
  1. Manny Machado, Padres, 10 years, $300 million (2019-28)
  1. Alex Rodriguez, Yankees, 10 years, $275 million (2008-17)
  1. Alex Rodriguez, Rangers, 10 years, $252 million (2001-10) That one broke a record at the time, as well, even if the Rangers would be desperate to get out from under it three years later, and traded him to the Yankees.
  1. Albert Pujols, Angels, 11 years, $240 million (2012-21)
  1. Robinson Canó, Mariners: 10 years, $240 million (2014-26)
  1. David Price, Red Sox, 7 years, $217 million (2016-22)
  1. Prince Fielder, Tigers, 9 years, $214 million (2012-20)
  1. Max Scherzer, Nationals, 7 years, $210 million (2015-21)
  1. Zack Grienke, D-backs: 6 years, $206.5 million (2016-21)

For the sake of this conversation about investment and results, we’ll remove Harper and Machado, just because they’ve only had one season each with their current teams. The Padres didn’t think they were one player away. But the Phillies may have tricked themselves into thinking they were when Harper came up the road from Washington, D.C., and then watched his old team finally win the World Series without him.

But of the rest of the guys on this list, three won a World Series with the team that signed them: A-Rod, Price, and Scherzer. Rodriguez had been with the Yankees since 2004, opted out of his old Rangers contract during the 2007 World Series, re-upped with the Yankees for the ’08 season. The Yankees won it all in 2009. They couldn’t have done it without him or another star free agent they signed before the ’09 season, a guy named CC Sabathia. CC’s not on the list, but he did get paid big by the Yankees at the time, $161 million for seven years.

In the third season after David Price signed his contract with the Red Sox, they won another World Series. And absolutely, hands-down, 100 percent don’t win it without him. Whether or not he’s always pitched like an ace since joining the Red Sox, when they needed him to pitch like a total star in the ALCS against the Astros, starting and relieving, he did that.

Scherzer did the same in this postseason for the Nationals, as they were winning the first World Series in franchise history. Max didn’t do it alone, none of these big-ticket guys ever do it alone, it’s baseball. But the Nationals don’t win without him showing the toughness and talent and athletic character he did, starting with the Nats-Brewers Wild Card Game, and all the way until Game 7 of the Series, as the Nationals waited one last time this October for late-game magic. And got it.

Prince Fielder is out of baseball now, at 35, because of injuries. But he did make it to the World Series with the Tigers in the first season after he signed his contract with them.

Again: Take Harper and Machado off the list. Way too small a sample size for either one of them. But of the others, three won World Series for the teams that signed them, and another – Fielder – played in one.

We look at the money, every single year, and think it’s crazy. The owners spending the biggest money, every single year, still do not. All this time after free agency came to baseball, they still like the odds. It’s why they keep finding money under the bed when they need it.