[The Dark]

Depending on how closely one hews to our timeline, by September 1997, Wesley Clark was no longer commanding SOUTHCOM (he departed in July); the head in September 1997 was Gen. Charles E. Wilhelm (USMC), who held the role until he retired in September 2000.

McGregor being intercepted by Cuban MiG-29s as currently described seems a bit odd. The maximum combat range for a MiG-29 for a high-altitude intercept with drop tanks is a little less than 375 miles, so they can barely reach the Yucatan peninsula from their base in San Antonio de los Banos (and can't reach Guantanamo without repositioning to another site first). Russian MiGs have somewhat longer range because Product 9.13 had two wet hardpoints and 9.17 increased internal tankage, but the Cuban MiGs (Product 9.12 and 9.51) only have one wet hardpoint and the smaller internal tanks.

What could work is to add a little more detail - if McGregor and company decided to skirt east around the MiG range, flying through the Windward Passage between Cuba and Hispaniola en route to either the Turks and Caicos or the Bahamas and then to the US, it would make sense that they could get caught off guard by MiG-29s that were reassigned to more eastern bases; normally, that flight path would be outside their range, but if they were moved to Holguin they'd be able to cover the Windward Passage. Being really nitpicky, the time of flight should also be a bit higher - the distance from Panama to Cuba is a minimum of 915 miles, and an airliner would need about 1.6 hours to cover that distance.