FAMILY TIME

Tom Brady enjoys Milan and celebrates Team USA's Women's hockey Olympic gold with his kids

Tom's wholesome moment comes after making flirty headlines

Tom Brady, American former professional football quarterback who played in the National Football League (NFL), attends the Serie A football match between AC Milan and Como 1907. The match ended 1-1 tie. (Photo by NicolÃ² Campo/LightRocket via Getty Images)

FEBRUARY 19, 2026 7:58 PM ESTFEB 19, 2026, 7:58 PM EST

Tom Brady is in Italy, enjoying the Winter Olympics with two of his mini-mes. The retired NFL star has been spending time in Milan for the games, and on Thursday, he watched Team USA's Women's hockey team win gold against Canada. Tom took to Instagram to share a photo of his son, 16-year-old Benjamin, with his friends, celebrating the win.

The trio raised their hands up, making W's in the picture with Tom tagging USA Hockey, writing, "Most Dominant Team in the world." Team USA won 2-1 with Megan Keller scoring the winning point in overtime. After the match, they celebrated with pizza and gelato.

Tom shared the post game meal of pizza and gelato

Benjamin was the only one in the hockey post, but Tom was also there with 13-year-old Vivian. He shares both with his ex-wife, Gisele Bündchen. On February 18, they were spotted as a group on a shopping trip in Milan. The only one who was missing was his oldest, Jack, whom he shares with Bridget Moynahan.

Tom Brady was spotted enjoying quality time with his son Benjamin Brady during a shopping trip to Golden Goose in Milan. The former NFL quarterback kept a casual look as they visited the store together. Brady is in the city alongside several athletes, including Italian and US Winter Olympians, with events taking place between Milan and Cortina.
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Tom Brady fue visto disfrutando de tiempo en familia con su hijo Benjamin Brady durante una jornada de compras en Golden Goose en Milán. El ex mariscal de campo de la NFL lució un atuendo casual mientras recorrían la tienda juntos. Brady se encuentra en la ciudad junto a varios atletas, incluidos olímpicos de invierno italianos y estadounidenses, con competencias celebrándose entre Milán y Cortina. — The group was spotted shopping in Milan before the game

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The pictures also show how tall his kids are getting. While Jack already beat him, standing at 6'8, Vivian and Benjamin didn't look too far behind him. Tom is 6'4, for context.

Vivian looked comfortable for their shopping trip, and tall!

Tom wore a khaki and green casual look for the outing with sunglasses and a shopping bag in hand. Vivian went for a comfortable vibe, wearing blue sweats, a zip-up hoodie, and slippers, while her big brother wore a trendy Off-White sweater by the late American designer Virgil Abloh, which retails at $650.

Family time after flirty time

Are Tom Brady and Alix Earle going to be this year's hottest new couple?

Tom's Olympic vacation with his kids comes after the 48-year-old has been making headlines with 25-year-old Alix Earle. The duo was first spotted in St. Barths on New Year's, then went viral again at a party in San Francisco for Super Bowl weekend.

Clips showed them dancing together with Tom getting handsy. A source later told Page Six they're having "fun."

While the insider noted it's "not-that-serious," they noted that the father of 3 is “very particular,” and an “intentional” “perfectionist” who “doesn’t hook up with just anyone,” so he must be genuinely interested in her.

Time will tell if we see Tom and Earle's 2026 love story turn from fling to something serious.