Long Island's Anthony Kay lives his dream, makes first career start at Yankee Stadium

White Sox pitcher Anthony Kay, a former star at Ward Melville High School, pitches against the Yankees on Wednesday at Yankee Stadium. Credit: Howard Simmons
Anthony Kay kicked up his right leg and his left arm came around, and he fired his first pitch with Paul Goldschmidt standing in the righty box for the Yankees. And those fans in Section 226, Row 11, high above the third-base dugout, could revel in the sight of a start in motion.
This was Anthony Kay Night for them at Yankee Stadium. For Anthony Kay, it wasn’t just another start for the Chicago White Sox, either.
The Kay family was a Yankees family when Anthony was growing up in Stony Brook. And that boyhood Yankees fan sitting in the stands and cheering them on back then was finally starting at the Stadium for the first time in his major-league career at the age of 31.
“It’s very special,” said Debbie Kay, Anthony’s mom, upon arriving. “We used to come here all the time to watch the Yankees, and now his dream came true.”
There were about 30 family members and friends around the ballpark Wednesday night to cheer him on.
“It’s incredible watching him living out his dream,” said Kerri Angelone, Anthony’s sister. “I know our [late] dad would be proud.”
The outing didn’t start well. Cody Bellinger hit a two-run homer in the first. Anthony Volpe cracked an RBI triple and Ali Sanchez singled him home in the second. But Kay put up a zero in each of the next two innings before manager Will Venable went to the bullpen for the fifth.
Family of White Sox pitcher and former Ward Melville star, Anthony Kay, on Wednesday at Yankee Stadium. Credit: Howard Simmons
The Yankees won, 10-5.
They extended a 4-3 lead with five runs in the fifth, keyed by Jose Caballero’s two-run single and Goldschmidt’s three-run home run.
“It was fun to be out there,” Kay said. “Obviously, I wanted some different results, but it was really cool and special to be out there.”
His line included the four runs, four innings, six hits, one walk, one hit batter and two strikeouts. He threw 86 pitches, 53 of them for strikes.
“Overall, the stuff felt pretty good,” Kay said. “I feel like I got a little bit unlucky today.”
Kay, now a Yaphank resident with wife Alyssa in the offseason, had appeared here twice in relief for Toronto. But this was so different for No. 18 in the road gray and his supporters.
“Obviously, we have seen him pitch here in the ballpark, but to be a starting pitcher means more than coming out of the bullpen,” said Bobby Kay, Anthony’s 39-year-old brother, wearing a home white No. 18 White Sox jersey with “KAY” on the back. “It’s your game . . . It’s great to see him starting. He’s always been a starting pitcher. It’s what he enjoys.”
He has generally been doing it well in this first season with Chicago after signing a two-year, $12 million deal with a mutual option for 2028.
The surprising White Sox are 38-34 and still in a virtual tie for first with the Guardians in the AL Central. Kay is 6-2. His ERA rose from 4.34 to 4.61, but he already has set career-highs in wins, starts (13), innings pitched (70 1⁄3) and strikeouts (55).
“Kay’s been huge for us,” Venable said before praising his tendency to get back on track after tough stretches. “I think it really speaks to the kind of competitor he is, a guy that trusts his stuff.”
Back at the beginning, Anthony’s dad, Bob, created a baseball environment for his two boys — a baseball field in the backyard.
“And he had all the advertisements along the fence,” Debbie said.
Bobby played at Ward Melville and was an All-America honorable mention pitcher at LIU Post. And then Anthony starred as a pitcher/centerfielder at Ward Melville for coach Lou Petrucci.
“He’s a great competitor,” Petrucci said Tuesday.
The Mets drafted Kay in 2013 out of high school in the 29th round. Kay went to UConn instead. Three years later, the Mets again took him with the 31st overall pick in the first round.
“Anthony always bets on himself, and he always wins,” Petrucci said.
The Mets traded him to Toronto in 2019. After four seasons with the Blue Jays and their affiliates, he pitched for the Cubs and the Mets in 2023. Then he was on to Yokohama in Japan the last two years. He set a BayStars record last season with a 1.74 ERA.
“In the major leagues, it was very difficult for him coming out of the bullpen but also going from the minor leagues to major leagues, bouncing around,” Bobby said. “Japan gave him a steady job pitching once a week as a starting pitcher, and he was able to develop a sinker.”
That led him to the White Sox.
“[This is] so much better,” his mom said, “because now I can actually go and watch him.”
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