Pitching Upgrades: 3 Pitchers the Bucs should Show Interest In this Offseason

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The Pittsburgh Pirates are facing a critical offseason where they need to make aggressive moves to upgrade their lackluster pitching staff. After years of bargain shopping for low-end rotation arms, it is time for the Pirates to finally invest in acquiring premium pitching talent. Building a competitive rotation capable of contending will require more than dumpster diving for back-end starters.

The Pirates must set their sights on legitimate arms that can transform the staff. In this slideshow, we'll explore three potential high-impact starters the Pirates should pursue: Jordan Montgomery, Jack Flaherty, and Frankie Montas. Any one of these pitchers would provide a massive boost. Landing an arm of this caliber would signal a bold new era and a real commitment to building a winner.

The Pirates have a chance to inject badly needed elite talent into the rotation. Let's examine why these three pitchers should top the wishlist for the Pirates this winter. Keep in mind, this is simply saying that the Pirates should be involved in these bigger names this offseason, with some being more realistic than others.

Left-hander, Jordan Montgomery

Of the three potential targets, Jordan Montgomery may come with the highest price tag but also the highest probability of success. He has consistently delivered results in the ultra-competitive AL East, posting a solid 3.20 ERA with 10 wins over 188.2 innings pitched this past season. Over his career to date, Montgomery has accumulated a 3.68 ERA with 38 wins over 755 innings pitched.

His extensive experience and demonstrated ability to eat innings would provide invaluable stability to a shaky Pirates rotation that has struggled badly in recent seasons. Although Montgomery will likely command the richest contract, his proven track record illustrates he is fully capable of elevating the Pirates' pitching staff to a much higher level of performance. He also is putting together a strong post-season with the Rangers.

Of the three pitchers profiled here, securing Montgomery should unequivocally be the number one priority for the Pirates this winter if the team is serious about fielding a competitive rotation next season. Landing a steady veteran lefty like Montgomery would set the tone for a new era of contention.

Right-Hander, Jack Flaherty

Jack Flaherty represents the high-upside wild card of the group of potential targets. The young right-hander possesses ace potential but also comes with some risk after an injury-plagued 2023 season. He is set to become a free agent at an intriguing intersection of youth and experience. Flaherty has flashed brilliance, such as his dominant run in 2019, but has also struggled to stay healthy and put together a full standout season from start to finish.

This past year, he posted middling numbers with a 4.99 ERA, 8 wins, and 148 strikeouts over 144.1 innings pitched. However, his career body of work remains solid, highlighted by a 3.75 ERA, 42 wins, and 748 strikeouts over 667.2 innings. If he can regain form and finally piece together a fully healthy year, Flaherty's aggressive pitching style and elite strikeout ability make him a pitcher who could anchor the Pirates' rotation for the next decade. Taking a chance on his immense but still unrealized potential gives the Pirates an opportunity to land a middle-of-the-rotation type arm capable of leading the staff if things go right.

It would also make a lot of sense for familiarity reasons. Flaherty had a long career with the the St. Louis Cardinals, making him more that known to the Bucs. Often times, players like to return to divisions they are comfortable in. After getting a taste of the AL east he may look for a pathway back into the NL Central.

Right-Hander, Frankie Montas

Of the three pitchers profiled here, Frankie Montas represents the most tantalizing talent but also the biggest injury risk. He missed nearly all of the 2023 season with recurring shoulder issues, appearing in just 1 game and pitching only 1.1 innings. When healthy, however, Montas has flashed true ace potential, as evidenced by his career 3.90 ERA, 37 wins and 612 strikeouts over 593.2 innings. His electric fastball reaches triple-digit velocity at its peak, and he has demonstrated the ability to dominate on the mound.

Nevertheless, the shoulder problems that wiped out his 2023 season raise some red flags. If Montas is able to regain his prior form and prove his health, he could emerge as a lethal rotation leader for the Pirates. However, after the injury-plagued year, Montas also brings substantial uncertainty in addition to his considerable upside. The Pirates would have to weigh the risks and potential rewards very carefully before pursuing Montas. Of the three options, he represents the most tantalizing talent but also the biggest question mark.

In the same breath, Montas could be the most likely option of the three. He is a former top-end starter who struggled in New York and is now coming off an injury. The fact that Montas would be seeking a one year prove it deal, the Bucs could be in play to make that type of contract offer.

In summary, the Pittsburgh Pirates have a prime opportunity this offseason to inject much-needed elite talent into their starting rotation.

Pursuing top-tier starters like Jordan Montgomery, Jack Flaherty or Frankie Montas would demonstrate a new level of aggression and competitiveness from the Pittsburgh front office. Any one of these arms would provide an enormous upgrade over the bargain bin veteran placeholders the team has relied upon in recent seasons.

Last year the Pittsburgh Pirates saw their young pitchers regress instead of improve. Roansy Contreras, Luis Ortiz, and Quinn Priester all were expecter to solidify their spots in the rotation in 2023. Instead, all three left the 2023 season without doing so.

Landing a pitcher of this high caliber would signify a bold new era for Pirates baseball. The time is now for the Pirates to make a splash by investing in a true rotation cornerstone capable of leading the team back to contention. By avoiding complacency and aiming high with one of these pitchers, the Pirates can put themselves back on the map with a revamped rotation and a bright future.

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