This story was excerpted from Justice delos Santos’ Pirates Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

It’s not hyperbole to describe this offseason as the most important winter of general manager Ben Cherington’s tenure in Pittsburgh.

The Pirates went from 62 wins in 2022 to 76 wins in ‘23, and should they make a similar jump in ‘24, they’ll likely make the postseason. Finding that extra dozen wins won’t just require internal development, but also external additions via trades, waivers, the Rule 5 Draft and, of course, free agency.

Here are four free agents who make sense for the Pirates this winter.

RHP Jack Flaherty

The last several years haven’t treated Flaherty all that well. Since 2020, Flaherty has pitched just 299 innings due to the COVID-19 pandemic and his own injuries. In ‘23, Flaherty’s first somewhat full season since ‘19, the right-hander had a 4.99 ERA and 4.36 FIP across 144 1/3 innings.

Flaherty doesn’t have the same fastball as when he emerged as a Cy Young candidate. Not only did Flaherty’s velocity drop (94.3 mph in 2019, 93.1 mph in 2023), but he’s gotten less horizontal movement, too (4.8 inches in 2019, 2.3 inches in 2023). The bet, then, would be on Flaherty’s willingness to evolve on the mound.

Flaherty has had success with his slider during his career, and last season several Pirates pitchers dramatically upped their slider usage. Flaherty, who posted a career-high 42.7% ground ball rate, could also benefit from leaning into his sinker, a once-prominent pitch in his arsenal that has been relegated to a cameo role (15.9% usage rate in 2018, 2% in 2023).

LHP Sean Manaea

Last December, Manaea signed a two-year, $25 million deal with the Giants that includes a $12.5 million player option for 2024. Manaea could accept his player option, but there’s a possibility that Manaea departs given how his year in San Francisco unfolded.

From 2016 to ‘22, Manaea made 156 starts and three relief appearances. In 2023, by contrast, Manaea appeared in 37 games, just 10 of which were starts. Manaea initially struggled with the oscillating role. In April and May, Manaea posted a 5.89 ERA and a 5.33 FIP across 36 2/3 innings. The underlying numbers weren’t all that pretty either. But things got better, and from June onward, Manaea recorded a 3.78 ERA and a 3.26 FIP across 81 innings.

2B/SS Jorge Polanco

Polanco, like Manaea, has an option for 2024, though Polanco’s is a $10.5 million team option for the Twins. Polanco currently faces an uncertain future due to the emergence of Edouard Julien, and the 30-year-old could very well find himself on the open market in several weeks.

Since 2019, the year he earned his first All-Star appearance, Polanco has slashed .268/.337/.458 with a 117 OPS+. Polanco isn’t an elite defender by any means, but he has the ability to play shortstop and third base in addition to second base. Polanco has been bitten by the injury bug the past two seasons, limited to 104 games in ‘22 and 80 games in ‘23. 

The Pirates have internal options at second base in Liover Peguero and Ji Hwan Bae plus Jared Triolo, depending on the roster shakes out, but they’d be best served to accumulate more depth at the position.

1B/2B Keston Hiura

Despite the Brewers’ offensive shortcomings, the team elected to keep Hiura in the Minors for the entirety of last season. The decision was jarring, given that Hiura mashed at Triple-A Nashville all season long. Across 367 plate appearances, Hiura slashed .308/.395/.565 with 23 home runs and a 137 wRC+. 

In 2022, the last time Hiura was in the Majors, he posted a .765 OPS with 14 home runs across 266 plate appearances. While Hiura’s K% (41.7%) was unsavory, he posted the best average exit velocity (91.7 mph), Barrel% (15.3%) and Sweet-Spot% (41.1%) of his career in the medium-length sample.