The Pirates may already have a bullpen answer sitting in the system - and that’s exactly why this offseason could get tricky.
Derek Diamond just picked up the organization’s Kent Tekulve Reliever of the Year honor after a strong run across four minor league levels, and the numbers explain the buzz. The right-hander went 7-0 with a 2.48 ERA, struck out 57 and walked only nine in 58 innings.
The best stretch came after he reached Triple-A Indianapolis in June. Diamond posted a 3.14 ERA with 39 strikeouts over 43 innings there, a line that made him look like someone who could be getting close to major league readiness. For a Pirates club that spent much of 2026 hunting for bullpen help, that matters.
But there’s a real roster squeeze coming. Diamond is eligible for the Rule 5 Draft, which means Pittsburgh has until Nov. 17 to add him to the 40-man roster or risk losing him to another team. That puts the Pirates in a bind, because this is the same bullpen that blew 20 saves before the trade deadline and forced general manager Ben Cherington to make several midseason moves.
Mason Montgomery’s rise gave the group a much-needed late-inning lift, and Luke Weaver added another experienced arm. Even so, the Pirates still need more dependable relief help if they want to build on their first winning season since 2018.
Diamond isn’t the flashiest pitching prospect in the system - he was a sixth-round pick in the 2022 MLB Draft - but he has a profile that plays. He has shown he can miss bats, keep walks down and handle Triple-A hitters, and his 1.02 WHIP across the minors backs up the idea that this wasn’t just a lucky run.
That said, the Pirates can’t treat one good season like a guarantee. Diamond still has to prove he can get big league hitters out on a consistent basis. The question is whether Pittsburgh wants to protect him now and keep the door open.
And he’s not the only one in that conversation. Catcher Axiel Plaz and infielder Jhonny Severino are also Rule 5-eligible, which only makes the 40-man roster math more complicated.
If the Pirates leave Diamond exposed, another club could take him in the major league portion of the Rule 5 Draft. That team would generally have to keep him on its active roster for the following season or send him back. A 25-year-old reliever with Triple-A success could look like a worthwhile gamble for a club looking for affordable bullpen help.
That’s the tension for Pittsburgh. The organization has poured years into pitching development, but the bullpen still let them down in 2026.
Diamond’s emergence gives them a chance to cash in on that work. Protecting him would cost roster flexibility.
Leaving him unprotected could cost them a pitcher who may be ready to help soon.
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