The Art Of Winning An (even More) Unfair Game

Epstein understood early that draft picks, like information, are a form of currency—so why not hoard them? During the 2002 season Port traded for lefthanded-hitting slugger Cliff Floyd, whom Epstein had no interest in re-signing. Epstein knew he could replace Floyd with a free agent—it turned out to be Ortiz, who worked out quite nicely—and get two compensatory draft picks after Floyd signed with another team. The Red Sox wound up with three of the first 49 picks in the '03 draft, each of which produced a future big leaguer (outfielders David Murphy and Matt Murton and pitcher Abe Alvarez). One player leaves, and you wind up with a net gain of two.

The industry narrative at the time regarding players in their free-agent walk years was, "I can't let him walk and get nothing but draft picks in return," a conviction that drove the trade market. But Epstein understood that the counter argument made more sense: "I'll let him walk and get the draft picks." As happened with on-base percentage, the rest of the industry has caught on and draft picks are cherished to the point where one of the hottest names in this year's trade market, San Diego closer and free-agent-to-be Heath Bell, went nowhere because the value of draft picks outweighed the players being offered in return.

In his early years as G.M., Epstein, like Beane, was more apt to use those picks on college players because statistical models indicated they were better bets to succeed than those out of high school. From 2003 to '06, the Red Sox used only a third of their picks on high school players. But by 2006, three years after Moneyball had spelled out Oakland's college-centric draft strategy, Epstein noticed the industry was focusing disproportionately on college players. High school players who would have gone in the second or third round before Moneyball were still on the board in the fifth or sixth.

So the Red Sox switched gears in 2007, the first year under Epstein in which they drafted more players out of high school than from four-year colleges. (They used 56% of their picks on high schoolers from 2007 to '11, nearly doubling their early rate.) One of those picks was Rizzo, a lefthanded-hitting first baseman out of Marjory Stoneman Douglas High in Parkland, Fla. Rizzo wasn't even the best prospect on his team; most scouts went to Douglas to see a catcher, Daniel Elorriaga-Matra. But when Laz Gutierrez, a Boston scout in the area, watched the team early in the season, he liked Rizzo. Rizzo did not run well and had a soft body—faults that turned off some scouts—but Gutierrez filed reports enthusing about the way the ball jumped off his bat to all fields and how smooth his hands and footwork were around the bag. Team cross-checkers Dave Finley, Mike Rikard and Marc Delpiano all concurred with Gutierrez.

The Red Sox, thinking they might have found a rare hidden gem, had Gutierrez lie low on Rizzo, which meant showing up only at big games when his attendance would not be construed as unusual. By the sixth round of the '07 draft, Rizzo was still available. Boston took him and paid him $325,000, a bonus generally reserved for a third-round pick.

Rizzo worked hard to transform his body. But the next year, at age 18, he was diagnosed with Hodgkin's lymphoma. After six months of treatments, including chemotherapy, Rizzo's cancer went into remission and he became one of the most liked and talented prospects in the Boston system. Last year he was named the organization's minor league player of the year. "He was an unbelievable inspiration, and everybody rallied around him," Epstein says. "We were just blown away with how this kid handled everything."

Under Epstein, the Red Sox have made 43 picks in the top three rounds of nine drafts. They have used only four of those picks on high school pitchers—five if you count Kelly, who wanted to be drafted as a shortstop and was prepared to play quarterback at Tennessee if he wasn't.

High school pitchers represent the biggest investment risk in the draft because pitching skills are harder to predict than hitting skills. The Red Sox won't take a high school pitcher high in the draft unless he is extremely polished. For Boston, that means the pitcher must have very clean arm action; a repeatable delivery; a natural feel for spinning the ball; a fastball that has not just velocity but also finish, deception or command; exceptional athleticism and great makeup. Kelly was the rare high school pitcher who met every criteria.

The area scout for Boston on Kelly was Anthony Turco, who had attended the same high school as the prospect, Sarasota High on Florida's Gulf coast. To keep Kelly from playing college football, Turco learned, a club would have to draft him as a shortstop and pay him first-round money. The problem for the Red Sox was that they considered Kelly a first-round pitcher but a third- or fourth-round shortstop.

Holding the 30th pick in the 2008 draft, the Red Sox had resolved to take Lonnie Chisenhall, a junior college third baseman—until Cleveland took him with the pick immediately before Boston's. The Red Sox scrambled. They got Kelly on the phone and cut a deal: They would give him a $3 million bonus and allow him to play shortstop and pitch. In his first two years in pro ball Kelly hit .219 with a .281 OBP and a .336 slugging percentage; he didn't pitch in 2008, but in '09 he had a 2.08 ERA and more than four times as many walks as strikeouts. After that season the Red Sox flew Kelly and his dad to their spring training complex in Fort Myers and explained that he could be the next Zack Greinke if he devoted himself full time to pitching. Three days later, Kelly called back and said, "O.K., I'll pitch." In 2010 he made the jump to Double A at age 20, and despite a 5.31 ERA, he was picked as the No. 1 prospect in the Boston system.