When it comes to draft strategies, Buster Posey and the San Francisco Giants are certainly trying to make waves, but the odds are stacked against them in their pursuit of UCLA’s standout shortstop, Roch Cholowsky. As the MLB draft approaches, Cholowsky is widely tipped to be the No. 1 overall pick, though there’s a bit of late chatter about prep shortstop Grady Emerson making a case for himself. The Giants, holding the fourth pick, have their eyes set on Cholowsky, with Posey reportedly enamored with the two-time Big Ten Player of the Year.

Cholowsky’s reputation as a top draft prospect has been solidified since the conclusion of the 2025 draft. His performance at UCLA has been nothing short of stellar, guiding the Bruins to a remarkable 51-6 record and securing the No. 1 seed in the College World Series.

His stats are eye-popping: a .353 average with a 1.190 OPS and 23 home runs as a sophomore, followed by a .338/.463/.707 slash line with 21 homers this spring. Standing at 6’2″ and 200 pounds, Cholowsky combines raw power with a keen eye at the plate, walking more than striking out.

Though his speed is average, his instincts, actions, and a plus arm suggest he could stick at shortstop.

Posey, in a savvy move, reportedly brought along Brandon Crawford, a UCLA alum and former Giants shortstop, to meet with Cholowsky. It’s a strategic play, considering Cholowsky grew up admiring Crawford.

In an effort to sweeten their draft pot, the Giants traded catcher Patrick Bailey to the Guardians, acquiring Matt Wilkinson and the 29th pick in return. This maneuver added $3.27 million to their bonus pool, now totaling $17,350,600.

The buzz is that this was done to potentially offer Cholowsky a lucrative overslot deal if he slips to them at No. 4.

The Giants’ strategy seems to be to entice Cholowsky with a hefty offer-perhaps around $13 million-hoping to drive up his demands with the teams picking ahead of them. The White Sox, Rays, and Twins are in line before the Giants, with Tampa Bay and Chicago boasting larger bonus pools. The idea is that Cholowsky could leverage a big offer to influence his draft destination, threatening to return to UCLA if his conditions aren’t met.

However, this tactic is fraught with challenges. For one, MLB is unlikely to look kindly on such draft manipulation, as it could set a precedent that undermines the draft’s integrity.

Moreover, Cholowsky would need to buy into this strategy, and there’s little indication he’s willing to risk his professional future or alienate potential suitors. If he’s offered a substantial contract by any of the top three teams, it’s hard to imagine him turning it down.

Additionally, the Giants are somewhat powerless here. Without the ability to trade first-round picks, they can’t offer much beyond a hope that Cholowsky plays along. In a draft where Cholowsky and Emerson are clear standouts, followed by Georgia Tech catcher Vahn Lackey and UC Santa Barbara pitcher Jackson Flora, the Giants are in a tight spot.

Posey’s tenure with the Giants has had its struggles, and this bold move for Cholowsky seems like a swing for the fences. But as it stands, the odds are slim that this strategy will land them their coveted player.