Mock Drafting The Pittsburgh Pirates’ First 3 Picks Of The 2026 Draft

The 2026 MLB draft is just days away. The Pittsburgh Pirates have a handful of picks within the first two rounds of the draft. Along with their normal first- and second-round picks, they also have a Competitive Balance Round A selection and a compensation pick for failing to sign Angel Cervantes last year. That gives the Pirates plenty of opportunities to add high-end talent early in this year’s draft. However, based on where they are selecting and who could be available, this is who they should take with their first three picks of the draft.

Mock Drafting The Pirates’ First 3 Picks Of The 2026 Draft

Jackson Flora (1st Round, 5th Overall)

So long as something completely unexpected doesn’t happen, UC Santa Barbara right-hander Jackson Flora will be one of, if not the best player available when the Pirates are on the clock with their first-round pick. There is a strong chance the college right-hander falls to the Pirates here at #5. Flora pitched 102 innings in his final college season, working to a microscopic 1.06 ERA, 0.853 WHIP, and 25.3% K-BB%. He struck out a third of the batters he faced while having a respectable 8% walk percentage. He allowed just three home runs all year, leading to an HR/9 ratio of 0.25. Of Flora’s 16 starts, two were complete-game shutouts.

Flora has three legit plus-or-better offerings. He sits mid-to-upper 90s with his four-seamer and tops out in the 100s. He doesn’t just throw pure heat, as his fastball also has good movement. Flora throws two variants of a slider. One is an upper-80s breaker with cutter-like action, and the other is an upper-70s pitch that moves more like a sweeper. His upper-80s kick-change is another pitch that looks like a plus offering. The right-hander’s curveball is the only pitch scouts aren’t overly bullish on; however, it is still a pitch he can mix in to change speeds and give batters a different look.

Flora has improved his control, despite his higher-effort arm action. Both Baseball America and MLB Pipeline rank him as the fourth-best prospect in this year’s draft class. He is also ranked as the best pitcher in the class by both sites. With how pitcher-heavy the Pirates’ drafts have been under Ben Cherington and how good they’ve become at developing pitching, Flora is certainly the player the Pirates should select if he is available at the fifth overall pick.

Andrew Williamson (Competitive Balance Round A, 34th Overall)

Andrew Williamson is the nephew of former Pirates utility man Sean Rodriguez. However, he is someone who should be on the Pirates’ early-round selection radar, beyond just the familial connection. Williamson is a well-rounded outfielder coming off a strong season at the University of Central Florida.

Williamson turned in a strong .322/.422/.645 triple slash, along with a .462 wOBA and 135 wRC+ over 265 plate appearances. The young outfielder hit for plenty of power, with 13 home runs and an isolated slugging percentage over .300, clocking in at .322. He also walked at a healthy 15.5% rate, with a strikeout percentage of 17.7%. 

Another thing of note is that Williamson has hit well in wood-bat collegiate summer leagues. Last year in the Cape Cod League, he had a .904 OPS, only struck out 13 times, and drew nine walks over 61 plate appearances. In 2024, he put up a 1.452 OPS in 132 plate appearances in the Cal Ripken Collegiate League, where he also drew more walks (20) than strikeouts (14).

While Williamson does not have one carrying tool, he does a lot of things right. His mechanics allow him to generate above-average pull-side power. However, there is concern that a hitch in his swing will give him trouble against premium velocity in pro ball. Still, at just 20 years old, there’s time for him to overcome that. Williamson is an above-average runner with a strong arm. He has a chance to stick as an average defensive center fielder but could end up as an above-average glove in a corner. MLB Pipeline likens him to former Pirates All-Star Nate McLouth. Both Pipeline and BA rank him as about a top 50 draft prospect this year.

Joseph Contreras (2nd Round, 44th Overall)

Joseph Contreras had about as good a showcase during spring as any young pitcher could ask for. The right-hander pitched for Team Brazil during the World Baseball Classic and impressed anyone who watched. Although he struggled in his two appearances, Contreras hit the upper-90s and induced a ground-ball double play from American League MVP Aaron Judge.

Although Contreras averaged around the upper-90s during the WBC, he usually sits around 92-95 MPH and tops out at 98. However, he just turned 18 in the first week of May, so there’s definitely a chance he can sit in the upper 90s in the future. He is also 6’4″ and 207 lbs, so there is some projection left. Contreras’ low-80s forkball is his best secondary pitch. He’ll also utilize both a slider and a change-up. Control is the biggest thing Contreras will have to sharpen up as he heads into pro ball.

The Pirates usually take a high school arm early in the draft. Since Ben Cherington took over as general manager, they’ve selected one prep pitcher with one of their first three picks in all but one draft, that being in 2022. Even then, they still took Michael Kennedy with their fifth pick that year. Given the Pirates’ proclivity to take younger arms in the first round or two of the draft and Contreras’ high ceiling, he makes a lot of sense for the Pirates here with their first pick of the second round.

Main Image Credit: Troy Taormina-Imagn Images