Yankees' 2021 MLB Draft Guide and Top Prospects to Target

The New York Yankees have the No. 20 overall pick in the 2021 MLB draft, and that opens the door for them to go a lot of different directions based on who falls.

It's the highest pick the Yankees have had since they rolled the dice on South Carolina right-hander Clarke Schmidt coming off Tommy John surgery with the No. 17 pick in the 2017 draft.

The only other time they had the No. 20 pick, they selected left-hander Eric Milton in 1996, and he went on to enjoy a solid MLB career with the Minnesota Twins after he was traded as a prospect in the Chuck Knoblauch blockbuster a year later.

Who might the Yankees be targeting this time around?

Ahead we've broken down three prospects who should be on their radar when their pick comes up in the 2021 MLB draft.

The 2021 MLB draft will kick off on Sunday, July 11, with the event coinciding with All-Star Weekend in Colorado and spanning three days and 20 rounds.

Beyond right-hander Jackson Jobe being a consensus top-10 pick, it's a thin crop of high school pitchers, and there could be just a handful of prep arms selected in the first round.

Andrew Painter should be among the select few to hear his name called somewhere at the back half of the first 29 picks. If he's still on the board at No. 20 overall, the Yankees would have an opportunity to add another power arm to their system.

The 6'7", 215-pound right-hander is already up to 96 mph with his fastball, and he has enough physical projection remaining to add even more velocity in the coming years.

"There are high school pitchers who garner a lot of attention because of huge raw stuff, and there are prep arms who have an advanced feel for pitching. When the two come together in one prospect, there's the chance for something special," MLB.com wrote in Painter's scouting report.

Prep right-handers always carry significant risk, but it's not out of the question to think Painter could wind up being the best arm in this entire draft class if everything clicks.

The Yankees are not afraid to take a chance on a top-tier talent that slips due to injury.

They proved that with the Clarke Schmidt selection, and Ole Miss right-hander Gunnar Hoglund fits a similar profile as a pitcher who was likely ticketed for a top-10 draft spot before he underwent season-ending Tommy John surgery.

The 6'4", 220-pound right-hander has four polished pitches and plus command, and he had a 2.87 ERA with 96 strikeouts in 62.2 innings through 11 starts before his season was halted.

The question is whether he'll still be on the board when the Yankees pick.

"I'll call it a one-third chance that Hoglund gets to the Yankees pick (he's in play at almost all of the half-dozen picks ahead of them) but very slightly less than that to become their pick, since there's also some chance he has a deal waiting for him later in the draft," wrote Kiley McDaniel of ESPN.

Gavin Williams (East Carolina), Ryan Cusick (Wake Forest), Sam Bachman (Miami, OH) and Michael McGreevy (UC Santa Barbara) are other college arms who could be in play for the Yankees.

While they have been frequently linked to pitchers throughout the mock draft process, the Yankees have selected a position player with eight of their 13 first-round picks over the last decade.

That list includes up-the-middle prep players Blake Rutherford, Anthony Seigler and Anthony Volpe over the past five seasons, and if they are not enamored with any of the arms left on the board when it's their turn to pick, they could turn their attention to the high school hitter ranks.

Pennsylvania prep outfielder Benny Montgomery is one of the best athletes in the draft class with an 80-grade speed tool and intriguing power potential packed into his 6'4", 200-pound frame.

"Teams that value more refined hitting skills will have Montgomery lower than where he's ranked here, while teams that prioritize raw tools and athleticism will have him pushed up their boards," wrote Baseball America while ranking him as the No. 23 prospect in the 2021 class.

The Yankees system is filled with tooled-up, high-ceiling prospects who will require some developmental time, and Montgomery fits the bill of the type of player they like to target.

All stats courtesy of Baseball Reference.