PLIVE+ Deep Sea Diving: Monthly Standouts

In this series, I'll be using PLIVE+, Prospect Live's secret weapon (which all MVP and Hall of Fame subscribers have access to), to uncover the next breakout prospects before anyone else. This week we're focusing on our top PLIVE+ monthly and weekly risers, another batch of FYPD standouts, prospects that seem to have made major strides this season, and a few players that have been on and off our radars over the last couple years. It's time to move on from struggling prospects that peaked in 2024 and start searching for the next potential big thing. Follow me @high_upside on X, and I'll be back Friday with this week's pitching prospects.

PLIVE+ Deep Sea Diving - Prospects LiveProspects LiveCharles Trimble

Weekly Risers

Yordany De Los Santos, SS, PIT

21 yo, High-A, 3% rostered on Fantrax, PL+ career/year 108/102 (-0.4 monthly change)

The 21-year-old has been on an absolute tear over the past week+ at High-A, with 5 doubles, 3 home runs, and 4 stolen bases over his past 6 games played. There’s too much swing-and-miss to his profile, but the raw tools are undeniable. He’s up to 7 home runs and 9 stolen bases in just 84 plate appearances this season. The 6'1 shortstop has put up a 103+ mph EV90 at Single-A over the past two seasons.

Yordany De Los Santos HOMER!

Hoppers: 11 | Dash: 4 pic.twitter.com/95madDga6z

— Greensboro Grasshoppers (@GSOHoppers) May 25, 2026

Emilien Pitre, 2B, TBR

23 yo, High-A, 3% rostered on Fantrax, PL+ career/year 104/94 (+2.2 monthly change)

Pitre is a big riser on our PLIVE+ weekly list, but he’s been solid since being drafted in 2024. The 2nd round pick out of Kentucky has slashed .271/.370/.392 in 779 pro plate appearances. He’s been on fire over the last couple of weeks, slashing .395/.578/.628 with 10 stolen bases (215 wRC+) in 64 plate appearances. The 2nd baseman also plays fantastic defense, if you care about such things.

Jack Winnay, 3B, BOS

22 yo, High-A, 0% rostered on Fantrax, PL+ career/year 105/92 (+4.2 monthly change)

Winnay is a top-10 weekly PLIVE+ riser, and for good reason. The 2025 13th round pick is slashing .390/.545/.805 with 5 home runs over his last 12 games (55 plate appearances), good for a 231 wRC+. He’s walked (42) more than he’s struck out (41) in his 229 professional plate appearances, while maintaining an 80% contact rate. The Wake Forest product is running an 89% zone contact rate this season.__ He also qualifies for the FYPD section, but I wanted him closer to the top of the article. He deserves it for what he's done this season.

Jack Winnay with a 2-homer game for Greenville yesterday! pic.twitter.com/nCkXnwyANA

— Red Sox Player Development (@RedSoxPlayerDev) May 17, 2026

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