6 ways the St. Louis Cardinals can win this week's MLB Winter Meetings

#4 Win the Draft Lottery OR fall outside the top-6

This is a fun storyline that I have been intrigued by for months now. Due to the MLB Draft Lottery rules, the Cardinals cannot select in the "lottery" (aka the top six) of the draft for more than two consecutive years. The Cardinals held the fifth overall pick in the 2025 MLB Draft, but since they selected seventh overall in 2024, they are eligible for the lottery this year.

Right now, the Cardinals have the ninth-best odds of winning the lottery, with UCLA shortstop Roch Cholowsky being the prize of the class as things currently stand. If the Cardinals jump into the top-six picks, they'll be ineligible for the lottery next year and won't be able to select higher than the 10th overall pick in the 2027 MLB Draft. Considering the Cardinals are entering a rebuild and may be bad next year, there is a real chance they would be in a position for a top pick again.

So, what should the Cardinals be hoping for on Tuesday? I think they should be hoping for one of two very different outcomes. Either...

A. Win the lottery
B. Select no higher than the seventh overall pick

If the Cardinals win the lottery this year, although they'd be barred from the top 10 in 2027, the chance to draft Cholowsky would be worth it. Not every draft has a slam dunk number one prospect, but Cholowsky seems to be that guy even seven months prior to the draft. Most scouts already view him as a 65-grade prospect with every tool except for his speed being graded at 60 according to MLB Pipeline. Yes, I know, the Cardinals have Masyn Winn and JJ Wetherholt, but Cholowsky is far too good a prospect for that to matter. All three can co-exist on the infield.

Moving into the top three wouldn't be bad at all, either, as high school shortstops Grady Emerson or Jacob Lombard could be great picks as well, as could other college bats like Justin Lebron or Derek Curiel, or they could keep adding to their stable of arms with someone like Liam Peterson or Cameron Flukey.

But if they aren't jumping up to the number one overall pick, selecting just outside the lottery would be ideal for the Cardinals. It would be really frustrating if they moved up to the fifth or sixth pick this year, and then could have had a top-three pick in 2027 but fell outside the top 10 because of them moving up a few spots this year. Go big or don't move at all, that's my opinion!