Red Sox Jaw-Dropping Lefty Pitching Prospect Faces Paul Skenes in MLB Debut

Payton Tolle, the Boston Red Sox top pitching prospect and No. 2 prospect overall, has experienced a jaw-dropping ascent through the minor leagues this season. After Boston made the TCU lefty their second-round draft pick last year, 50th overall, the former collegiate two-way player made his professional debut with the High-A level Greenville Drive on April 8.

In the space of one season and just 18 minor league starts across the Single-A, Double-A and Triple-A levels, Tolle is set to make his Major League debut on Friday, after being promoted by the Red Sox on Thursday.

Tolle Skyrockets Through Red Sox Farm System

The organization had just promoted Tolle to the Triple-A Worcester Red Sox in early August. He made only three starts at the minor leagues’ top level before getting the call to join the big league club at Fenway Park. After a rough first inning at the Triple-A level, Tolle allowed just one run over his next 14 innings across three starts before getting the call-up.

Tolle also skyrocketed up the MLB Pipeline prospect rankings, debuting in the top 100 at No. 100 on July 18, climbing all the way to No. 28 by the day of his promotion to the big leagues just six weeks later.

The Good News For Red Sox Prospect

Now, he will take the mound at Fenway Park on Friday night for his initiation into the Major Leagues. For Tolle, the good news is that he will be facing the Pittsburgh Pirates, the worst offense in MLB. The Pirates’ 484 runs scored rank last among the 30 teams, as does the team OPS of .657.

The Pirates have the fewest home runs as well, with 98 — the only team with fewer than 100 home runs.

And the Bad News

The bad news for Tolle is that the opposing pitcher on Friday will be Pittsburgh’s Paul Skenes, the 2023 No. 1 overall draft pick who raced to the big leagues after just 12 minor league starts.

The matchup features two of the more physically imposing pitchers in the game. Skenes stands 6-foot-6 and weighs in at 260 pounds. Tolle is also listed at 6-foot-6, and 250 pounds.

Skenes not only leads the Major Leagues with a 2.07 ERA, his most recent start on August 24 was the 50th of his career, which means that Skenes has the second-lowest ERA after the first 50 starts of a career since the “live ball” era began in 1920.

Only Vida Blue of the Oakland A’s, who made his 50th start in 1972, had a lower ERA at 2.01.

Skenes Favorite For NL Cy Young

Well on his way to the National League Cy Young Award, last year’s NL Rookie of the Year and Cy Young third-place vote-getter — behind winner Chris Sale of the Atlanta Braves and runner-up Zack Wheeler of the Philadelphia Phillies — Skenes has struck out 181 batters in 161 innings while walking just 27. He also leads the Majors in pitchers’ wins above replacement (WAR) at 6.2.

While Tolle will be making the first start of his career for the Red Sox, Skenes’ start will be his first against the Red Sox. The Pirates’ ace is 23 years old, but only five months older than Tolle. Both were born in 2002, Skenes on May 29, Tolle on November 1.

The start will also be the second of the season for Skenes in which he faces a highly-ranked rookie pitching prospect. On June 25 he faced the Milwaukee Brewers and their fireballing 6-Foot-7 rookie Jacob Misiorowski. In that matchup, Skenes came out on the short end, giving up four runs in a highly uncharacteristic second inning as the Brewers hung on for a 4-2 victory.

Alex Cora Raves About Under-The-Radar Read Sox Leader

When the Boston Red Sox signed Alex Bregman, he drew rave reviews for how he contributes both on and off the field. He’s been described as an extra coach at times, always helping others improve.

He’s not the only team leader the Red Sox acquired this offseason, though. The team signed Aroldis Chapman last winter, and while he’s been excellent on the mound, his clubhouse contributions have gone under the radar.

On the field, Chapman has been excellent. He hasn’t allowed a hit in over a month, and his 1.02 ERA is a career low. It was announced on Sunday that Chapman had signed a contract extension to remain with the Red Sox through at least 2026, with an option for 2027.

The extension wasn’t just earned because of his on-field performance, though.

“He’s very quiet, you see him in the clubhouse, but he knows the game, he’s been through a lot. I know in that bullpen, his voice, it means something,” Red Sox manager Alex Cora said.

Chapman has been the anchor at the back of the Red Sox bullpen. In close games, the team almost always turns to Garrett Whitlock and Chapman for the final two innings. They’ve done an excellent job of managing their workloads, but may need to lean on them more frequently as they push for the playoffs.

“You think about guys that impact the team, we always talk about Alex [Bregman] and then Trevor [Story], but quietly and in his own way, he’s one of the leaders of this team,” Cora said.

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