Major League Baseball’s amateur draft was held last week, and though it hardly holds the cachet of the NFL or NBA versions, it’s still where most of the future marquee names in baseball come from. The current Yankees roster boasts no fewer than six former first-round picks.

During the late 1990s and early on into this decade, the Yankees gained a reputation as one of the worst drafting teams in the game. In 1992, the team selected Derek Jeter, a high school shortstop out of Michigan with the sixth overall pick. Since then, the team has made 20 first-round selections, of which only two have worn a Yankees uniform: top prospect Philip Hughes, who had his debut earlier this season, and Ryan Bradley, a right-hander who pitched in a total of five games in 1998.

More recently, the Yankees have significantly changed course where drafting is concerned. Spearheaded by the team’s scouting director, Damon Oppenheimer, the Yankees now flex their financial muscle in the draft in the same manner they do in the free agent market each winter. Since they are always picking late in the first round because of a winning record the year before, and sometimes without a first-round pick at all because of a free-agent signing, the Yankees no longer play it by the book, instead waiting for players who have dropped because of eligibility problems, and opening that pinstriped checkbook to get them signed.

So far, the gambit has been met with mixed results. In 2005, the Yankees gave eighth-round pick Austin Jackson $800,000 — the kind of sum usually reserved for a second-round selection — to lure him away from a college basketball scholarship. Today, Jackson remains in Low-A and is doing little to suggest he’ll ever reach the majors. Three rounds later in that same draft, the Yanks gave thirdround money to righthander Alan Horne, a pitcher who is currently among the minor league leaders in strikeouts, and who could be contending for a bigleague job next year. The big gamble last year was on Dellin Betances, the 6-foot-9 teenager from New York who could touch 98 mph with his fastball. The only team willing to give him a cool $1 million to buy him out of college was the Yankees, so they did just that, selecting him in the eighth round.

With the final pick in this year’s first round, the Yankees selected a North Carolina State righthander, Andrew Brackman, and while they have yet to sign him, he looks to be the team’s biggest gamble yet. Three years ago, Brackman was among the Wolfpack’s top recruits — in basketball. A 6-foot-10-inch power forward, Brackman was committed to hoops, averaging nearly 20 minutes per game as a freshman, but he never walked away from the diamond, joining the baseball squad once basketball season ended. He pitched in 10 games his freshman year, striking out a batter per inning; scouts were intrigued, and wanted to see more. He followed a similar pattern in 2006, joining the school’s baseball team late and appearing in just seven contests. That summer, he pitched in the Cape Cod League, an elite college-level league that included many of the top professional prospects in the game, and he dominated, allowing just two runs and seven hits in 17 frames. Having grown closer to 6-feet-11-inches and sporting a fastball that touches 99 mph, Brackman was considered one of the best amateur prospects in the game on ceiling alone, though his lack of experience left him raw for his age. More tantalizing still, in the fall of 2006, Brackman announced that he was leaving the basketball team to focus solely on his baseball future, and he came into spring ranked in the top five on the draft boards of most teams.

When the college baseball season opened in late February, Brackman was installed as North Carolina’s Friday starter (the college equivalent of an ace), and he pitched like one early on. Because of his size, his upper-90s heater looked as if was coming out of the sky, and he impressed observers with smooth mechanics and a rapidly improving breaking ball. Then suddenly, in late March, he became a little more hittable, and by April, the wheels came off. Brackman was suddenly getting hit hard, his fastball had dipped into the low 90s, and his control had abandoned him. Scouts were concerned, as one of the open questions concerning the youngster entering the season revolved around durability. Talent evaluators had seen him pitch well, but not over a long period of time, and his sudden drop-off became a red flag that sent his stock plummeting.

In a 10–7 Wolfpack victory against Virginia on May 12, Brackman lasted just four innings, needing 101 pitches to get even that far. While he gave up a modest three runs, he also walked five, and surrendered five hits, getting into jams in each inning. It was the last chance anyone had to see him pitch before the draft. The next weekend, Brackman was pulled from his starting job because of what scouts classified as “arm soreness.” Giving a player of Brackman’s importance a rest before the conference tournament made sense, but then he didn’t pitch in the next weekend’s Atlantic Coast Conference tourney, and he sat out once again a week later as his team was knocked out of the NCAA tournament.

Between his uncertain health, late-season swoon, and his selection of super-agent Scott Boras to represent him, Brackman was suddenly a draft-day leper. Although he was once seen as a potential top-three pick in the draft, Brackman was suddenly untouchable in the first round. Enter Yankees. With the final pick in the draft, the Yankees were anticipating that one of Boras’s many highpriced talents would fall to them. After the first 29 picks were off the board, the team had two interesting choices: Brackman, and a high school pitcher from Connecticut, Matt Harvey, who had also not lived up to preseason expectations. They went with Brackman.

Despite all of the negative marks on his record, Brackman will surely demand a signing bonus that eclipses the $1 million that one normally associates with the 30th pick in the draft. If we go by Boras’s track record with regard to players he considers to be special, Brackman will likely require a more complex deal that includes not only a major league deal (and the associated 40-man roster spot) but a total package in the $4 million to $6 million range.

It’s a risk for the Yankees, but much like drafting Betances last year, it’s one that they are in a unique position to take. Based purely on pure potential, Brackman ranks with any player drafted. His combination of size and velocity (when it shows up) is something that scouts see perhaps once in a generation. At the same time, the gap between what Brackman is now and what he can be is wider than the Grand Canyon. Four years from now, he will either be a dominating starter for the Yankees, or another footnote in the team’s miserable recent draft history.

Mr. Goldstein is a writer for Baseball Prospectus. For more state-of-the-art commentary, visit baseballprospectus.com.