Pittsburgh Pirates: Top Five Starting Pitching Free Agents To Pursue

Let's take a look at what I consider the five best free agent starting pitchers the Pittsburgh Pirates should pursue this off-season

The Pittsburgh Pirates desperately need starting pitching this off-season. If the season were to start next week, the only starters they’d have are Mitch Keller and Johan Oviedo. Both are far from bad options, but as of right now, the last three spots are left up to Quinn Priester, Luis Ortiz. Roansy Contreras, Bailey Falter, Andre Jackson, or Osvaldo Bido.

Sure, there are prospects coming up through the system, such as Paul Skenes, Jared Jones, Anthony Solometo, Bubba Chandler, Thomas Harrington, Braxton Ashcraft, and Jackson Wolf, all of whom could make a bid for a rotation spot sometime during the 2024 season. The Pirates will also see both Mike Burrows and JT Brubaker return sometime during the summer. However, adding both stability and longevity to the starting rotation is an absolute must this off-season.

The starting pitching free agent market may be shallower than in years past, but there are still some free agents the Pirates should pursue. Today, I want to list my top five free agent targets I think the Pirates should at least look into, if not heavily pursue.

Number Five: Lucas Giolito

Lucas Giolito is a very good potential rebound candidate. The former Chicago White Sox’s ace is coming off a horrible second half of 2023. However, along with a solid first half of the season, the right-hander was considered one of the better pitchers in the league only a few seasons ago. For what he might cost, the risk could potentially be worth the money.

Giolito started the 2023 season with the White Sox, pitching to a respectable 3.79 ERA, 4.43 FIP, and 1.22 WHIP across 121 innings. Giolito struck out a touch over a quarter of the opponents who stepped into the batter's box against him (25.8%), while having an 8.3% walk rate. Where Giolito struggled was home runs with a 1.49 HR/9 rate. Overall, these numbers aren’t too impressive, but he only really had two bad starts, that being his second start of the season and his second to last start with the White Sox.

Despite these two outings only making up 6.3% of his total innings in the first half of the season, they made up 29.4% of the earned runs he allowed. Take out these two outings, and he drops to a 2.86 ERA and 3.85 FIP. Giolito spent most of the second half of the year with the LA Angels and Cleveland Guardians, where his numbers completely tanked.

Through his final 63.1 innings of the year, Giolito saw his numbers rocket up to a 6.96 ERA, 6.87 FIP, and 1.48 WHIP. While he maintained the same striekout rate at 25.4%, his walk rate went up to 10.8%, and his HR/9 doubled to 2.98. His home run rate could decrease simply given a larger sample size. His HR/FB ratio was over 25%, which is completely unsustainable, especially given he was allowing less hard contact. Once adjusting with xFIP, he had a better, albeit still poor 4.65 xFIP.

You also have to consider it was just a few seasons ago that Gioltio was a fine starting pitcher From 2019 through 2021, Giolito worked to a quality 3.47 ERA, 3.54 FIP, and 1.08 WHIP. Gioltio had a strikeout rate a shade above 30% (30.7%), while also carrying an 8% walk rate. Home runs were always a worry with him, but a 1.24 HR/9 is much more manageable than what he put up in 2023.

Giolito is one of the biggest rebound candidates currently on the free agent market. He’ll likely get a one-year deal with an option for another year or two, depending on his market. Given his poor 2023, it wouldn’t be all that surprising if he was looking to rebuild some of his value before re-entering the free agent market for a larger contract.

Number Three: Shota Imanaga

The only reason Shota Imanaga is third and not second is because the second free agent option is a proven MLB pitcher. Regardless, Imanaga will be one of the best international players who will likely head to America this off-season. Imanaga had a career-best season for the Yokohama Bay Stars.

In 159 innings, Imanaga worked to a 2.66 ERA, 1.02 WHIP, and 7.83 K:BB ratio. The lefty had a 29.5% K-rate along with an outstanding 3.8% walk rate. His K:BB ratio was the single-best rate of his career, beating out his previous career high set in 2022 by 3.11 strikeouts. The only blemish was his below average 1.02 HR/9, which still isn’t horrible.

Imanaga has an impressive resume to his credit. Of the seven seasons where he pitched at least 100 innings, he posted a sub-3.00 ERA six times, including now four straight seasons with an ERA under 3.00 in at least 149 innings pitched. It is also the second straight season with a WHIP below 1.00. 

Imanaga does not throw too hard, sitting in the low-90s. His primary breaking pitch is a cutter/slider hybrid. His secondary breaking ball is a curveball, and his off-speed pitch is a splitter. But he has decent command that should translate if he decides to come to the United States. 

Imanaga will be the second best professional international pitcher available, assuming he and our number one player on today’s list both are posted and make their way over from Japan. Imanaga has pitched to an all-star caliber level in Japan for multiple years now. He’d certainly be worth going after, and given how the Pirates have hinted at their pursuits on the pro international market, I could see them heavily pursuing the lefty. After all, Ben Cherington loves lefty starting pitchers.

Number Two: Jordan Montgomery

In my opinion, if either of the international options are not viable, Jordan Montgomery the best potential free agent target the Pirates should go after on the starting pitching market. The southpaw is coming off a strong season between the St. Louis Cardinals and Texas Rangers and will be looking to secure a potential long term deal. Montgomery fits almost perfectly into the Pirates’ roster.

The lefty tossed 188.2 innings for the Cardinals and Rangers last year, working to a strong 3.20 ERA, 3.56 FIP, and 1.19 WHIP. Montgomery’s 21.4% strikeout rate was not good, but pretty typical for him. His 6.2% walk rate was also very close to his career average, but he did post a career-best 0.86 HR/9 rate. Montgomery was slightly above league average in inducing soft contact with an 88.3 MPH exit velocity (65th percentile), 37.9% hard-hit rate (58th percentile), and 7.5% barrel rate (59th percentile).

Montgomery had a great season, but he didn’t pitch all that much differently from 2021-2022 to 2023. His exit velocity, hard-hit rate, and barrel rate from 2023 are all pretty much identical from the prior two seasons. His walk rate is also nearly identical, and his strikeout rate is roughly the same. xERA, xFIP, SIERA, and DRA- also support the claim that he’s pretty much the same pitcher in 2021-2022 as he was in 2023 despite a career-low ERA.

While Montgomery isn’t an old pitcher, he will go into the free agent market going into his age-31 season (turns 31 on December 27th). But he gives the Pirate exactly what they need; a reliable left-hander who both produces above average results and is durable. He has started at least 30 games in each of the last three seasons and has the 17th most innings pitched since the outset of the 2021 campaign.

The Pirates put about $17 million combined toward Vince Velasquez, Rich Hill, and Austin Hedges. If the Pirates were to offer Montgomery a multi-year contract worth $17 million a season? A good comparison I found was Chris Bassitt. He pitched to a very similar 3.42 ERA, 3.66 FIP, and 1.15 WHIP in his contract season, and received a three-year/$63 million deal (an AAV of $21 million). While Bassitt’s performance was very similar to Montgomery’s in their platform season, Bassitt is slightly older. The first year of his new deal, he was 34, compared to Montgomery’s age-31.

Montgomery isn’t going to be cheap, but if the Pirates are willing to slightly increase their off-season spending, I could very much see them going after Montgomery. I’d expect something like a four-year deal with an AAV around $18-20 million, which isn’t a massive uptick to what they spent on Velasquez-Hill-Hedges last off-season. 

Number One: Yoshinobu Yamamoto

Who doesn’t want Yoshinobu Yamamoto on their team next season? Yamamoto is a superstar pitcher in Japan, having pitched his entire career with the Orix Buffaloes. Yamamoto entered the 2023 campaign as the NPBs best pitcher. But not only has he solidified that title, he’s surpassed it in any way imaginable. 

Yamamoto is having an unbelievable season in Japan. In 171 innings, Yamamoto has a 1.16 ERA, 0.86 WHIP, and 6.29 K:BB ratio. Yes, you read that right, a 1.16 ERA. He is in prime Bob Gibson territory. He has allowed just two home runs all year, and has a walk rate of 4.2%. Put it like this: Yamamoto is within a half run of Gibson’s 1968 season, and has a lower walk rate than Greg Maddux had throughout his entire career. It also helps that Yamamoto is a decent strikeout pitcher with a 26.7% K-rate.

The right-hander has some of the best athleticism you can get from a pitcher. He’s been able to translate that into outstanding command. Keep in mind that this will be his third straight season with a sub-6% walk rate. Yamamoto throws hard, sitting in the mid-90s but can reach back and hit 98-99 MPH when needed. Even then, his fastball is a potential plus-plus pitch because of his ability to manipulate it. His best secondary is his splitter, but his curveball also is a plus offering, and his cutter looks like an average pitch.

While Imanaga consistently posts ERAs under 3.00, Yamamoto consistently posts ERAs under 2.00. This is now the third straight season Yamamto has posted an ERA below 2.00, and the fourth overall time he’s accomplished this in his career. His highest single-season ERA is from the 2017 season when he was an 18-year-old rookie. Despite his age, he still had a quality 2.35 ERA. That’s how good Yamamoto has been; his worst single-season performance still saw him have a sub-2.50 ERA, and he was just 18.

Yamamoto is probably going to cost a lot. I’d estimate him to receive a contract similar to that of Masahiro Tanaka, which was a seven-year/$155 million contract. Still, the Pirates have hinted at being aggressive in the professional international scene this winter. In my opinion, Imanaga is much more likely, but I do believe the Pirates will give an honest effort in going after Yamamoto.

Honorable Mentions

Hyun Jin Ryu

Hyun Jin Ryu has missed a good portion of the last two seasons. He underwent elbow surgery in ‘22 after making just six starts, and reappeared in August of 2023. However, Ryu returned strong, pitching to a respectable 3.46 ERA, 4.91 FIP, and 1.29 WHIP in 52 innings of work. While the veteran Korean lefty had a strong 6.3% walk rate, he also had a poor 17% strikeout rate, and even worse 1.54 HR/9. But his HR/FB ratio was just over 4% greater than his career norm. Even if he isn’t an ace like he was at his peak, he could still serve as a solid 3.80-ERA sort of pitcher.

Tyler Mahle

Tyler Mahle got off to a great start to the 2023 season, pitching to a 3.16 ERA, 4.19 FIP, and 1.05 WHIP in April. But the season didn’t last long for the right-hander, as he underwent Tommy John surgery in early May. If Mahle hadn’t undergone Tommy John surgery, he’d probably be in the top five of today’s list. I still wouldn’t be opposed to signing Mahle, but given that he probably wouldn’t return until May at the earliest, I’d want to see the Pirates to go after a more immediate solution. But I also wouldn't be upset if he was a starter the Pirates went after after acquiring some other starters.

Frankie Montas

Frankie Montas is another rebound candidate. The right-hander missed pretty much all of the 2023 season, pitching 1.1 innings at the end of this season. Montas underwent shoulder surgery in February, which caused him to miss nearly the entirety of the season. But Montas was a quality pitcher in 2021-2022, working to a 3.67 ERA, 3.55 FIP, and 1.20 WHIP in 2021-2022.

Luis Severino

Luis Severino is our second former Yankee honorable mention and rebound candidate. Severino returned from Tommy John surgery in 2022 with a 3.18 ERA, 3.70 FIP, and 1.00 WHIP through 102 innings. While hopes were high he could continue to be a quality starter for the Yankees, Severino fell flat, tossing just 89.1 innings, and posting a horrid 6.65 ERA, 6.14 FIP, and 1.65 WHIP. Severnio was effective as recently as 2022, so a low-cost one-year deal could work wonders.

Michael Lorenzen

Michael Lorenzen went from Comerica Park in the American League Central to Citizens Bank Park in the National League East. Needless to say, the transition didn’t go over super smooth. After an all-star first half with the Tigers, Lorenzen faltered down the line and was even moved to the bullpen. But signing Lorenzen would get him back into a more pitcher friendly environment, and has been a fairly solid pitcher over the last handful of seasons. The veteran righty owns a 3.88 ERA (113 ERA+), 4.18 FIP, and 1.27 WHIP dating back to 2018.  But this was the first year since 2015 Lorenzen both pitched out of the rotation for nearly all of his season and stayed relatively healthy enough to make at least 20 starts.