As the Yankees pondered what to do with their 20th-round selection on Day 3 of the MLB Draft, Damon Oppenheimer felt the time was right to take his shot.

The Yankees selected Jack Leiter, a right-handed pitcher from Delbarton School in Morristown, N.J., a hurler ranked No. 33 by MLB Pipeline heading into the Draft.

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Leiter, the son of former Yankees pitcher and broadcaster (and current MLB Network analyst) Al Leiter, is committed to Vanderbilt University, where he intends to play next season. His perceived lack of signability caused all 30 teams to pass on the talented 19-year-old through the first 19 rounds, and even though the Yankees knew the chances of signing him were slim-to-none, Oppenheimer thought it was the right move with the 615th overall selection.

"In the 20th round, Jack was obviously the best player on the board," said Oppenheimer, the Yankees' vice president of domestic amateur scouting. "I know his deep commitment to Vanderbilt, but there's always a percentage chance that something could happen. As minute as it is, it's there. Vanderbilt is the most likely scenario, though."

Leiter had been the best player on the board since sometime in the second round, but going under the presumption that he's planning to attend Vanderbilt, wasting a pick in the first half of the Draft didn't seem to make sense.

In Round 20, however, Oppenheimer decided it was time.

"At that point, it becomes a balancing act," Oppenheimer said. "You know you're probably not going to be able to get him signed in those rounds, so why use the pick? In the 20th round, I'm weighing my odds there; that less-than-1% chance or those relationships, they're worth it at that point."

The relationship part of the decision shouldn't be overlooked, as the Yankees will now lay a foundation with Leiter for future years.

"Jack is going to be a Draft-eligible sophomore in two years, and the idea that the Yankees will have been a big part of his graduating from high school and moving on, it could help us out with information at that point, access to him at that point, stuff like that," Oppenheimer said. "There's a time where there are relationships that are built through some of this."

Monday, the Yankees selected Leiter's Delbarton teammate, shortstop Anthony Volpe, with the No. 30 pick in the first round. Volpe is also committed to Vanderbilt, but the Yankees seem confident they will be able to sign him.

"I think both kids made good decisions," Delbarton coach Bruce Shatel told nj.com Monday night. "Jack wanted Vanderbilt and Anthony wanted to play pro ball right now. Both kids had the full support of their families."

If the Yankees try to sway Leiter to change his mind with a signing bonus exceeding $125,000, it would count against the roughly $7.45 million in bonus-pool money they have to spend on their 11 picks from the first 10 rounds.

Each pick in the first 10 rounds of the Draft has an assigned value, and the total for each of a club's selections equals what it can spend on signing bonuses for players selected in those rounds without incurring a penalty. If a player selected in the first 10 rounds doesn't sign, his pick's value is subtracted from his club's pool. If a team exceeds its allotment, it faces a penalty.