Buster Posey's gambit for SF Giants to land Roch Cholowsky reeks of desperation

The SF Giants hold the No. 4 pick in the 2026 MLB Draft and if recent reporting from USA Today reporter Bob Nightengale is to be believed, San Francisco is trying to push for their favorite player. It’s been clear for a while that the Giants have an interest in UCLA shortstop Roch Cholowsky who many believe will go No. 1 overall to the Chicago White Sox, but the way president of baseball operations Buster Posey is going about it reeks of desperation.

Apparently, Posey has met with Cholowsky and they have also had franchise legend Brandon Crawford meet with the young shortstop. They are clearly pulling out all the stops to try to make this happen no matter the odds. Cholowsky is a Vallejo native who has said he grew up cheering for the Giants and looking up to Crawford so it would seem like a perfect pairing if San Francisco drafted him.

The only problem is that three teams draft ahead of the Giants in July’s MLB Draft. While Cholowsky is considered by many to be the best overall player, it’s not unanimous. Some think the White Sox could go another direction. MLB Pipeline’s Jim Callis has talked about how the Giants could create chaos by trying to get Cholowsky but he has had a hard time envisioning a scenario in which Cholowsky falls to No. 4.

Many have speculated that San Francisco’s trade with the Cleveland Guardians that sent catcher Patrick Bailey away in exchange for prospect Matt “Tugboat” Wilkinson and the No. 29 overall pick in the draft which also gave the Giants more bonus pool money to spend on draft picks could help them land Cholowsky. 

Posey's attempt to get cholowsky to fall to Giants seems destined to fail

That’s probably San Francisco’s only realistic avenue to land Cholowsky. They have to scare teams into thinking that Cholowsky will not sign whatever rookie deal they offer him and that San Francisco’s offer will be so big that no one else can compete. Even then, Cholowsky has somewhat limited leverage and Posey himself has even said that conversations about bonus pool money are a bit overrated and that teams usually just draft the player they want.

Maybe if the Moneyball-era Oakland A’s were drafting ahead of the Giants that would allow Cholowsky to fall to them, but that’s not the case. The White Sox have shown a willingness to pay money and try to compete in recent years so they probably wouldn’t be afraid to pay Cholowsky but maybe they like Grady Emerson better. The Tampa Bay Rays pick second and have done well at winning on a budget so maybe they’d chafe at a big signing bonus for Cholowky. The Minnesota Twins pick third and seemed like they were going to sell the team recently so maybe money is a factor for them.

There’s a way to envision it happening, but it still feels unlikely. Really, this feels more like Posey recognizing this season is going south for the Giants and wanting to make a big move to get fans excited about the team's future. It's admirable that he would try and one of Posey's strengths is that he is willing to make big moves like he did last year with the Rafael Devers trade. Still, it just feels like a desperate attempt to land the top guy even though deep down Posey probably knows this gambit is unlikely to succeed.

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