A Peculiar Left Side Story in Boston

This article was originally published as part of Verducci’s View, a weekly baseball newsletter from Sports Illustrated senior writer Tom Verducci. Every Monday, Tom empties out his notebook over email and covers MLB’s hottest topics, provides in-depth analysis through both text and video breakdowns, looks forward to what’s worth watching during the week and more. If you want to be featured in his new mailbag, please email newsletters@si.com with any questions about MLB or his decades in the sport.

The Red Sox have two left-handed rookies in their rotation who are 25 or under, Payton Tolle and Jake Bennett. That has happened only once before in franchise history (minimum 12 starts): in 1949, when Mickey McDermott, then 20, and Chuck Stobbs, 19, combined to go 16–10 for a Boston team that won 96 games and finished second.

Stobbs made his major league debut at 18 and was traded at 22 to the White Sox, who flipped him soon to the Senators, where he became part of Washington’s colorful if inglorious legacy. Stobbs gave up the mammoth 1951 home run to Mickey Mantle that sailed out of Griffith Stadium and birthed the concept of the tape measure home run. Yankees PR director Red Patterson measured the blast at 565 feet.

Five years later, Stobbs threw what was purported to be the wildest wild pitch ever: a pitch that landed 17 rows deep into the stands. The next year, 1957, he entered in the 10th inning of the final game of the season with a record of 8–19. He promptly gave up hits to all three batters he faced and took loss number 20.

Tolle, 23, and Bennett, 25, are more promising—and oddly alike. They are tall lefties that get down the mound with elite extension. Indeed, the Red Sox have a type they prefer. There are only 35 lefties with an extension of 6.7 feet or greater (min. 500 pitches). Six of them have pitched for Boston this year: Tolle, Bennett, Garrett Crochet, Connelly Early, Erik Miller and Aroldis Chapman.

That’s not all Tolle and Bennett have in common:

	Payton Tolle	Jake Bennett
Hometown	Bethany, Okla.	Bixby, Okla.
Throws	Left	Left
Age	23	25
Height	6'6"	6'6"
Weight	234	250
Draft Round	Second	Second
Extension	7.3	7.1
2026 ERA	3.30	3.17
Career High IP (including college)	108 1/3	117
2026 IP	107	116

Those last two categories are fascinating. Tolle and Bennett with their next starts will set career highs in innings pitched—with still eight or nine starts remaining in a pennant race and then the postseason looming. The Red Sox must find a way to give them some rest down the stretch, especially because of how hard they’ve been worked. Tolle has made six of his 19 starts on four days rest (one day less than standard) and Bennett five of 13.

Most Innings on Four Days Rest, U-25 Lefthanders, 2026

Player	IP
1. Parker Messick, Guardians	57
2. Jake Bennett, Red Sox	30 2/3
3. Payton Tolle, Red Sox	30 1/3

Wilson’s Model (and Record) Glove

Jacob Wilson of the Athletics on Sunday played in his 111th consecutive game without an error, breaking the shortstop record held by Mike Bordick. Defensive metrics are so notoriously unreliable that Outs Above Average wants you to believe that Wilson has gone from a below-average defender last year (-3) to elite this year (+8), thanks in part to his range improving from -2 to +6.

Says Athletics manager Mark Kotsay, “He may not have the elite range Statcast likes, but he is in the right place at the right time, makes every play and has a cannon for an arm. He is fundamentally as sound as it gets.”

A SPARKLING play by Jacob Wilson 🤩 pic.twitter.com/nNFBNtYJwl
— MLB (@MLB) April 4, 2026

When you watch Wilson play shortstop, pay attention to his feet. He has exceptional footwork while possessing an uncanny knack for reading hops. You almost never see Wilson in position of trying to field a bad hop.

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