Pittsburgh Pirates: Previewing the Left-Handed Starting Pitching Market

The Pirates have signed one LHP SP every off-season in Ben Cherington's reign, so what does this year's market look like?

Aug 4, 2023; Arlington, Texas, USA; Texas Rangers starting pitcher Jordan Montgomery (52) pitches
Aug 4, 2023; Arlington, Texas, USA; Texas Rangers starting pitcher Jordan Montgomery (52) pitches / Jerome Miron-USA TODAY Sports
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Ben Cherington has signed one left-handed starting pitcher every year since taking over as GM Pittsburgh Pirates. What does this offseason's left-handed starting pitching market look like?

Veteran left-handed starting pitchers seem to be Ben Cherington’s specialty. Since taking over as the Pittsburgh Pirates general manager, he’s signed one veteran left-handed pitcher in each of his offseasons.

In 2020, it was Derek Holland. The next year, he signed Tyler Anderson. 2022 was José Quintana, and this year, it was Rich Hill. The Pirates might sign multiple starting pitchers this off-season, but I’d put money that at least one will be a veteran lefty starter. So, what does that market look like heading into the offseason?

James Paxton

A high-risk/reward option is James Paxton, who, up until recently, was having a quality rebound season with the Boston Red Sox. Through his first 15 starts of the year, Paxton had a 3.36 ERA, 3.86 FIP, and 1.15 WHIP. He had a strong 27.4% strikeout rate and a 6.7% walk rate, but his HR/9 of 1.34 was underwhelming at best.

However, over his last five outings, he’s 18 earned runs in just 15.2 innings. Paxton may be breaking down. This is the first time since 2019 he’s pitched more than 20.1 innings. He made just six starts in 2020-2021 combined, then didn’t pitch at all in 2022.

Hyun-Jin Ryu

Hyun-Jin Ryu is one of the older but still effective lefty starting veterans. Ryu has only pitched in 34 innings but has only allowed ten earned runs for a 2.65 ERA. His 5.8% walk rate is another outstanding remark on his 2023 report card, and he’s held opponents to an 85.9 MPH exit velocity.

Ryu has never been a big-time strikeout pitcher, and his 20.3% strikeout rate is only slightly worse than his career average of 21.7%. Ryu’s 1.32 HR/9 is up, but given he has a massive 17.2% HR/FB ratio, a ground ball rate at 50%, and has been holding opponents to soft contact since his return, it’s evident he’s run into some bad luck.

Alex Wood

There are a few veteran lefties looking to rebound after a rough 2023. One is Alex Wood. Wood has bounced between the starting rotation and bullpen but has just a 4.77 ERA, 4.73 FIP, and 1.46 WHIP to his credit. Wood’s 0.98 HR/9 is about the only silver lining of his season. He’s struck out well under 20% of opponents with a 17.6% strikeout rate but has also struggled to limit walks with a 10.3% walk rate. But it wasn’t all that long ago Wood was a quality starting pitcher.

Martin Perez

If there’s one lefty SP who’s looking to rebound, it’s Martin Perez. Perez has followed up his All-Star 2022 campaign with a disappointing 4.88 ERA, 5.34 FIP, and 1.49 WHIP. Perez has pitched 125 innings in 28 games (20 starts). He’s struggled with home runs, with a 1.51 HR/9, though his 14.2% strikeout rate and 8.2% walk rate aren’t out of the ordinary for him. Perez has pitched better but still not great since getting moved to the pen.

Matt Boyd

Matt Boyd is a left-handed starter who has some peripherals backing his uninspiring 5.45 ERA. Aside from that ugly number, Boyd owns a 4.36 FIP, 4.38 xFIP, 4.20 xERA, 4.26 SIERA, and 102 DRA-. All of that suggests he’s more of a league-average starter rather than one with an ERA that is hovering around 5.50.

Boyd has a solid 24.1% strikeout rate and 8.3% walk rate, though home runs have always been an issue, and while his 1.39 HR/9 is one of his better single-season career rates, it’s still higher than you’d like to see.

Clayton Kershaw

Admittedly, the chances of him leaving LA would be slim to none at this point in his career, but Clayton Kershaw will be hitting the open market again, and it would be extremely fun if the Pirates signed him. Kershaw has battled injuries over the last few years, which have diminished his Hall of Fame career only slightly. Kershaw has still been an effective pitcher, but given that 2024 will be his age-36 campaign, he’s probably not leaving LA until he hangs up the cleats.

Blake Snell

Blake Snell is another veteran LHP SP on the free agent market but is probably way out of the Pirates’ price range. He might even win the National League Cy Young. At the very least, he will likely be a finalist. However, like with Kershaw, while it is extremely unlikely the Pirates land Snell, it would be an extremely fun time if the Pirates were able to get him to sign.

Jordan Montgomery

If there is one lefty veteran who might still be in the Pirates’ price range and would be a major rotation upgrade, it would be Jordan Montgomery. Monty has a 3.46 ERA, 3.63 FIP, and 1.23 WHIP. His 21.2% strikeout rate and 6.5% walk rate are both nearly in line with his career averages.

But his 0.87 HR/9 rate has been the best of his career thus far. The lefty is basically pitching to his career norms and has consistently been both solid and durable. If I had to choose one free agent to go atop of my Pirates FA wishlist, it would be Montgomery.

Wade Miley

The last two LHP SPs we’ll look at have mutual options, though these rarely get accepted. The first is Wade Miley, who has a 3.33 ERA, 4.92 FIP, and 1.14 WHIP in 100 innings with the Milwaukee Brewers this season. Though, there are some red flags here. His 15.8% strikeout rate is low, even for him. His 1.34 HR/9 is also the worst rate he’s put up since 2017. Granted, there are some things that are working in his favor, such as his above-average 87.3 opponent exit velocity, as well as his 7.4% walk rate. 2024 will be his age-37 campaign, so keep that in mind.

Eduardo Rodriguez

The last pitcher is probably one of the best pitchers on the free agent market, and that’s Eduardo Rodriguez. Rodriguez has rebounded to the tune of a 3.11 ERA, 3.30 FIP, and 1.12 WHIP with the Detroit Tigers this season.

E-Rod has a 24.4% strikeout rate, which is slightly higher than his career 23.9% rate, but his 6.6% walk rate is the best of his career. He also has an 0.8 HR/9 rate and is in the 68th percentile of exit velocity. However, do be slightly weary of his home run rate. Rodriguez has an 8.6% HR/FB ratio, the first time he’s ever posted a sub-10% ratio. Comerica Park is one of the most pitcher-friendly parks in baseball, with the lowest home run park factor among all 30 teams.

In Review

If I had a say in the matter, I think Montgomery is the guy the Pirates should go after. Montgomery has been both durable and consistent since 2021. He's on pace for his third straigth season with 30+ starts and an ERA+ of 112 or greater. However, a mid-tier veteran like Wade Miley, Hyun-Jin Ryu is also someone I wouldn't be upset if the Pirates signed. Sure, they're older and are coming off injury-laden 2023s, but they've still been effective despite said injuries.

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