Pippa Middleton's Difficult Year: Everything That's Troubled The Future Queen's Little Sister

It might be safe to say 2026 was a no good, very bad year for Pippa Middleton. Everything that could possibly go wrong did, and then some. Pippa might live a really lavish life, but it's not without its problems, though we'd be remiss not to note that Princess Catherine's sister's riches are part of what caused her problems.

2026 saw Pippa and her husband, James Matthews, in an almighty brawl with their Berkshire neighbors. The couple obstructed a footpath that used to be accessible to the public. The path runs through their Barton Court Estate, and to tighten security, the pair installed an electric gate to keep people out. This understandably did not go down well with Berkshire residents, who took their case to the City Council. Chairman of the West Berkshire Ramblers, Eugene Futcher, told The Mail on Sunday that people have been using the footpath for years, and that alternative routes aren't really an option. "It will force people onto the main road, which is very dangerous," he argued, per GB News. 

Alas, Pippa's diva behavior didn't end there. She and Matthews also constructed an illegal car park smack in the middle of a National Landscape that also happens to have been endowed with enhanced protections. Though the land is part of their estate, they had to seek planning permission to build it, which they didn't. They only did so after construction was complete. West Berkshire Council ordered in August 2026 that the car park be removed.

Their Barton Court Estate wasn't the only piece of land Pippa Middleton and James Matthews owned. They also purchased Bucklebury Farm in 2020. On the surface, it looked like a great idea. It had a lot to offer and came with some nice trimmings, including a petting zoo, glamping sites, a children's play area, and a cafe, not to mention the 44-acre deer park. All in all, one would expect tourists and locals alike to flock to such a place. Unfortunately, Pippa's controversial reputation among her neighbors hurt her business. Some complained to the Daily Mail that Pippa and her husband were exploiting people with the ticket prices. One resident decried it as a "snooty cash grab," adding, "This was a childhood favourite growing up in Berkshire, but since the Middleton takeover it has become a place of snobbery and middle-class inclusivity."

In an attempt to make the farm more profitable, Pippa decided to open a nursery on the grounds, citing the lack of establishments in the area to care for young children during the day as the main driver behind the idea. The community raised concerns about increased traffic in the area, but the Daily Mail reported in August 2025 that Pippa was eventually given the go-ahead by the City Council. This reporting was refuted by Hello! in May 2026, when it came to light that Pippa and Matthews had not received approval for the nursery and were running the farm at a loss that had accumulated to an eye-watering £807,543 (about $1 million) by 2025. With the couple's only bid to save the property denied, they cut their losses and sold it.