The Leonardo DiCaprio friendship drama has taken another turn as reports suggest Tobey Maguire has found himself sidelined while DiCaprio forms a new bond with Sean Penn. The brewing tension surfaced after the two Oscar winners worked closely together, reportedly leaving Maguire, DiCaprio’s long-time friend, feeling left out and unsettled.
DiCaprio and Penn’s Growing Connection Raises Eyebrows
Leonardo DiCaprio and Sean Penn became close while filming One Battle After Another, released this September, and sources now claim the two have been nearly inseparable since. While both actors previously maintained friendly ties, their recent collaboration appears to have deepened their connection, creating a new dynamic that excludes old friends. Tobey Maguire, once an integral part of DiCaprio’s inner circle, is said to be struggling with this shift.
Maguire and DiCaprio, who grew up in the spotlight together and famously co-starred in The Great Gatsby as neighboring characters, have had one of Hollywood’s most enduring friendships. But since Sean Penn entered the picture, insiders hint that the bond is under considerable strain. Reportedly, the change is most apparent in their social interactions, where Maguire now finds himself on the outside looking in.
Insider Claims Maguire Is Upset by New Dynamic
“It’s bumming him (Tobey) out, big-time – but right now Leo’s made his choice, and Tobey’s not involved at all,”
an insider told RadarOnline.
According to the insider, Sean Penn has specifically requested more exclusive time with DiCaprio, further driving a wedge between the childhood friends. Their shared appreciation for Italian food has reportedly been one of the factors strengthening DiCaprio and Penn’s relationship. This newfound camaraderie has left Maguire, now a father of two, feeling sidelined as DiCaprio focuses on his connection with Penn.
Other Friends Also Reportedly Distanced
The DiCaprio friendship drama might not be limited to Maguire. Reports also mention Bradley Cooper, who previously had a close rapport with DiCaprio, is now less involved. Cooper’s current relationship with Gigi Hadid – DiCaprio’s former partner – seems to have caused some distance between the two actors, suggesting DiCaprio’s circle is rapidly shifting.
Despite rumors of a falling out, there is talk of possible reconciliation. According to reports, DiCaprio and his girlfriend Vitoria Ceretti joined Maguire for Thanksgiving celebrations just last week, hinting at lingering bonds and hope for rekindling their long-standing friendship.
Origins of the New Friendship
DiCaprio and Sean Penn have shared a casual acquaintance for years, introduced through mutual friend Robert De Niro. However, it was not until 2024 that the two developed a close personal friendship, with Penn quickly becoming a significant presence in DiCaprio’s life and altering the established group dynamic that long included Maguire.
The ongoing Leonardo DiCaprio friendship drama continues to capture attention, as insiders and fans alike speculate on the fate of one of Hollywood’s most prominent friendships. As DiCaprio’s ties to Penn grow stronger, the impact on his relationships with former friends like Maguire and Cooper is likely to shape the social landscape around the acclaimed star in the months to come.
