A Walk in the Park: Anthony Kay Took the Long Way to Game 2
By Jess Henderson ·
In the fifth inning on Saturday in Cleveland, Anthony Kay needed 11 pitches to get through the top of the Guardians' order. Steven Kwan tapped a sinker back to him. José Ramírez popped the first pitch he saw to shortstop. Chase DeLauter grounded out to first. The White Sox won Game 1 of the American League Division Series 3-0, and that inning was the least dramatic part of Kay's afternoon. On Monday at Progressive Field, those same three hitters are lined up to see him first.
Will Venable confirmed on Sunday that Kay will open Game 2, with Sean Burke behind him, per MLB.com. First pitch is 4 p.m. Central. The Associated Press counted it as the 33rd time this season Chicago has used an opener, the third in the postseason. The reason starts with a platoon split. Left-handed hitters batted .183 and slugged .257 against Kay this season. Right-handers hit .293 and slugged .489. Kwan and DeLauter bat left-handed.
Kay is 31, and he took the long way to this assignment. The Mets drafted him 31st overall out of UConn in 2016, and he had Tommy John surgery that October before throwing a professional pitch. In 2019 they traded him to Toronto with Simeon Woods Richardson for Marcus Stroman. Over five seasons with the Blue Jays, Cubs and Mets, he had a 5.59 ERA and made seven starts in 44 appearances. Between December 2022 and October 2023, three different teams claimed him off waivers. The last of them, the Athletics, outrighted him off the 40-man roster that November, and he elected free agency.
That is usually where a pitcher gets filed under first-round picks who did not work out. I understand why the file exists. I just think it gets closed too early, especially on a left-hander who was 28 and had never made more than five starts in a big-league season.
In January 2024 he signed with the Yokohama DeNA BayStars. He had a 3.42 ERA in 24 games that first year, and in October, with Yokohama down two games to one in the Japan Series, he struck out the first four SoftBank hitters of Game 4 and threw seven scoreless innings in a 5-0 win in Fukuoka. The BayStars won the series. In 2025 he had a 1.74 ERA over 155 innings and led the Central League with a 67.8 percent ground-ball rate, per the AP.
Yokohama Stadium sits inside Yokohama Park, about a two-minute walk from the south exit of Kannai Station, and the BayStars sell game-day tickets from an office in the park. I have wanted to see a game in Japan for years, mostly to watch how the ballparks and the trains fit together. A ballpark you reach by walking through a park was already near the top of my list. Kay pitched there for two seasons and came back a starter.
When he signed a two-year, $12 million deal with Chicago in December 2025, he said starting every turn in Japan, after years of being up and down and designated for assignment, helped him "develop and be consistent and find myself," per MLB.com. He also pointed to Garrett Crochet, who went from the White Sox bullpen to their rotation, as a sign the club had a plan for pitchers like him.
The plan mostly held. Kay made 31 starts, went 10-9 with a 4.44 ERA over 158 innings and became the first White Sox lefty with double-digit wins since Carlos Rodón in 2021, according to the AP. He also hit 26 batters, nine more than any other pitcher in the majors. Against Cleveland he made four starts and allowed three earned runs in 20 innings.
In October he has pitched out of the bullpen. In Houston on Sept. 30, he came into the fifth inning of the Wild Card clincher with two runners on and one out, got Yordan Alvarez to line out, walked Isaac Paredes to load the bases and got Jose Altuve to fly out to right. On Saturday he took over in the fourth with two outs and a runner on first. Travis Bazzana doubled on his first pitch and Austin Hedges walked, and then Brayan Rocchio lined out to Braden Montgomery in right. After that came the 11-pitch fifth.
"He's made some really big pitches, got us out of some really tough spots," Venable said, per the AP. Kay put it more simply to MLB.com. "It's been fun," he said.
On Monday the job is the top of the order, and probably not much more. Burke had a 3.34 ERA and 185 strikeouts in the regular season and, per MLB.com, a 1.04 ERA in 17 1/3 innings against Cleveland. Gavin Williams starts for the Guardians after going 14-8 with a 3.76 ERA and 248 strikeouts, second in the majors. Cleveland is trying not to go to Chicago down two games.
Ten years after the Mets drafted him, and after two seasons in Yokohama, Anthony Kay starts a major-league postseason game for the first time. If Cleveland's lineup holds from Saturday, it goes to Kwan.
Book of the Week
I said I was done buying books until the pile on my nightstand got shorter. The pile is the same height, plus one. Chad Harbach's The Art of Fielding follows Henry Skrimshander, a shortstop at Westish College, a small school on the shore of Lake Michigan, who looks headed for the big leagues until a routine throw goes badly off course. The rest of the novel stays with five people knocked sideways by that one throw.
There is less baseball in it than the cover suggests, and more about friendship, ambition and starting over, which made it good company this week. The paperback runs 544 pages, so it does not fit in a jacket pocket. It fits in my bag, next to a book I have not opened in three weeks. I dog-ear the pages I want to find again. So far that is most of the fielding scenes.