Westgate Resorts

In the same eighteen-month window, Westgate lost the founder who personally selected every executive on its leadership page, installed a new CEO, new COO, and its first permanent CIO in over a decade of stability, and simultaneously closed its largest acquisition ever, opened its first international resort, and handed its 30,000-square-foot Las Vegas sportsbook over to a different company's technology platform. None of that is a crisis — Westgate just made TIME's inaugural list of America's Best Private Companies and Forbes' Best-in-State Employers, both in 2026 — but it is a company actively re-examining its own vendor relationships and technology roadmap at exactly the moment a fresh conversation lands best.

For Connection, that's the opening: a newly installed CIO with a public mandate that explicitly includes "cybersecurity, infrastructure, and guest technology innovation" is a CIO who hasn't yet locked in every vendor decision for the next five years.

Across multiple Westgate properties — Westgate Lakes Resort & Spa, Westgate Town Center, and Westgate Vacation Villas Resort, all in the Orlando/Kissimmee cluster — guests have posted TripAdvisor reviews over several years describing connectivity as "terrible," unable to support a phone or a gaming device, with management acknowledging the complaints without a fix showing up in later reviews. This isn't a single bad week at one property; it's a recurring, guest-documented pattern spanning some of Westgate's highest-traffic Central Florida resorts.

It's a low-drama, high-credibility opener precisely because it isn't a security incident — it's a guest-experience and brand problem that a managed, centrally monitored Wi-Fi refresh solves directly, and it's the kind of finding a CIO can act on without a board conversation first.

In April 2026, Caesars Entertainment and Westgate Las Vegas Resort & Casino announced that Caesars Sportsbook would take over operation of the legendary Westgate SuperBook — the world's largest sportsbook at 30,000+ square feet — pending Nevada Gaming Commission approval. It went live in July 2026 with more than 20 self-service wagering kiosks, expanded mobile wagering, and on-property account registration, all running on Caesars' own platform and technology stack inside a building Westgate still owns and operates.

That's a brand-new, real-money-adjacent, third-party-operated system integrated directly into Westgate's network — worth a proactive network-segmentation and vendor-risk review now, while the integration is only months old, rather than after an incident forces the question. Framed as "let's make sure this is walled off correctly" rather than "something's wrong," it's a genuinely low-friction ask.

Three of Westgate Las Vegas's Strip neighbors have been hit by major cyber incidents in under three years: MGM Resorts' September 2023 ransomware attack (claimed by the Scattered Spider group), Caesars Entertainment's August 2023 breach and ransom payment, and a Wynn Resorts data-breach class action filed in February 2026. Westgate itself has no public breach on record — genuinely a clean sheet — but it now shares a technology integration with Caesars specifically, and sits in the same target-rich neighborhood as all three.

As of 2024, Westgate has faced multiple active class-action lawsuits alleging high-pressure timeshare sales tactics, including a claim that closing agents were given a "closing portfolio" containing required legal disclosures in a concealed pocket, and a separate Military Lending Act claim alleging a military couple was kept in a five-hour sales presentation. These are allegations in ongoing or recently filed litigation, not adjudicated findings, and Westgate has faced and resolved similar claims before — a $900,000 telemarketing-practices settlement in 2009 is the oldest one on record.

Regardless of how any individual case resolves, a documented, timestamped, audit-trail record of what was disclosed and when — call recording, e-signature capture, CRM-logged consent — is a genuine protection for the company and for the sales team delivering thousands of in-person and phone presentations a year. That's a defensible technology conversation independent of any case's merits.

A wildfire swept through Gatlinburg, TN in late November 2016, forcing an evacuation of roughly 500 guests and staff from Westgate Smoky Mountain Resort & Spa; preliminary reports at the time indicated the fire destroyed more than 100 of the resort's buildings, and one couple had to be rescued from a stuck elevator by eight fire crews. A separate, unrelated structure fire hit a building still under reconstruction in 2018, with no injuries reported. Both are a decade or less old and the resort has since rebuilt (its own site runs a "Westgate Heroes" rebuilding retrospective) — included here for what it says about the wildfire and hurricane exposure across Westgate's geography, not as evidence of an ongoing safety problem.

The Westgate SuperBook's Big Game viewing party is a genuine Westgate-run annual tradition — the world's largest sportsbook viewing party, 30,000+ square feet, 350 reserved seats, sold out every year it's been held. The Westgate Foundation also runs an annual Military Weekend celebration. Both are real and recurring, but neither has a public sponsorship prospectus the way IAAPA or HITEC do — they read as guest-facing entertainment and community events, not open vendor-sponsorship channels. Worth raising directly with Miranda or Saft as a possibility rather than assuming a package exists to buy into.