Brewers' head-scratching offseason blunder continues to worsen

Yesterday afternoon, the Milwaukee Brewers announced that they were sending 2024 fifth-round draft pick, John Holobetz, to the Boston Red Sox as the player to be named later in last month's trade for Quinn Priester. The team also sent No. 7 prospect Yophery Rodríguez and the 33rd pick in this year's MLB Draft to the Red Sox in order to acquire Priester. While it has yet to be determined how this trade will pan out for both sides, there was a rather easy way for Milwaukee to avoid the trade altogether, had they simply made a different decision during the offseason.

Way back in November of 2024, the Brewers were deciding which prospects to add to their 40-man roster in order to protect them from the Rule 5 Draft. In brief, the Rule 5 Draft is an opportunity for MLB teams to select players from other organizations so long as they add them directly to their own 26-man active roster and adhere to certain roster restrictions for a minimum of 90 days during the subsequent season. Players are eligible to be selected in the Rule 5 Draft if they were signed at age 18 or younger and have played five seasons in the minor leagues or if they were signed at age 19 or older and have played four seasons in the minors, according to MLB.com. Rule 5 eligible prospects can be protected by the organization adding them to their 40-man roster.

The Brewers ultimately decided to "protect" Logan Henderson and Chad Patrick from the Rule 5 Draft, while leaving one notable pitching prospect vulnerable to selection by another MLB club: Shane Smith. When the Rule 5 Draft occurred, on December 11th of last year, Smith was the first overall selection, snatched from the Brewers organization by the Chicago White Sox. The Brewers "replaced" Smith on their roster by taking a Rule 5 pitcher of their own, Connor Thomas of the St. Louis Cardinals.

Now, nearly five months later, that decision is still haunting the Brewers' front office, as its fallout has led to the Brewers losing two promising prospects and a high 2025 draft pick, in addition to Smith himself.

Losing John Holobetz is the latest effect of the the Brewers' surprising Shane Smith decision

When the Brewers were seemingly losing a starting pitcher to injury every day at the beginning of the season, they became desperate for a rotation arm that could provide immediate help, while also offering long-term value. This desperation ultimately led to the Priester deal — a deal that many Brewers fans are deeming a lopsided trade in favor of the Red Sox.

Meanwhile, Smith has posted a 2.41 ERA in his first seven starts with the White Sox, including a five-inning outing against the Brewers in which he only allowed one earned run. In other words, Smith has been the steady MLB-ready starting pitcher that the Brewers were searching for when they traded for Priester.

However, the big difference between Smith and Priester is that keeping the former would not have cost the immense amount of prospect capital that it took to acquire the latter. Instead, all the Brewers would have had to do was add Smith to the 40-man roster back in November 2024 and elect not to make a selection in the Rule 5 Draft, which is an option that all teams hold.

Yes, it is very difficult to predict how certain pitchers will pan out when they reach the big leagues, and Thomas, the Brewers' Rule 5 selection, held promising numbers in Triple-A a season ago (2.89 ERA in 90.1 IP). However, even if Thomas and Smith were the same caliber pitcher — which has not been the case so far as Thomas posted a 20.25 ERA in his first five innings with the Brewers before landing on the IL — it would have made more sense to keep Smith, because he would not have been tied down to the roster restrictions that Thomas is as a Rule 5 selection.

It is absolutely too early to offer a definitive analysis of both the Priester trade and the decision not to protect Smith, as MLB.com's Adam McCalvy pointed out in an article this morning. However, what can be noted is that because the Priester trade happened in the wake of the Smith decision, and likely wouldn't have occurred if Smith had been on the Brewers' roster at the time, it's fair to say that Priester has to not only outperform the combined value of Holobetz, Rodríguez, and whoever Boston selects with the 33rd pick in this year's draft, but also has to outperform Smith in order for the entirety of this decision to be worthwhile for the Brewers.