SIESTA KEY, Fla. ‒ Standing in water that nearly reached her calves, Kathleen Killeen extended her thumb as a robust ex-military transport truck approached along the road.

Driver Nicholas Weppner, 24, shifted gears and brought his 5-ton truck, affectionately dubbed “Big Boy” by his father, to a halt with a jolt.

“Need a lift?” he shouted out the window.

Just hours prior, Hurricane Milton had made its presence known on this once-idyllic barrier island, scattering its renowned “#1 Beach USA” sand on the road, tearing down signage, and damaging local establishments, all while the community was still grappling with the aftermath of Hurricane Helene just a fortnight earlier.

After rising before dawn as the storm subsided, Weppner and his girlfriend managed to get past police at one of the bridges and drove their 6 x 6 truck onto the island, determined to lend a hand.

A car enthusiast, Weppner had purchased the 1985 M923 a few years back for fun. He also works as a field insurance underwriter with X Insurance. No one prompted him to take his truck to Siesta Key, but he anticipated it would be necessary.

Once she climbed up into the truck, Killeen, 76, secured her hair into a ponytail, settled onto the bench seat, and observed as Weppner’s vehicle navigated the main road of the island, Midnight Pass Road.

She was still reeling from the recent events: Just two weeks prior, Hurricane Helene had unleashed a deluge of water on the island, flooding numerous homes, apartments, and vacation rentals. Although Milton’s feared storm surge late Wednesday was milder, its winds were stronger than anticipated.

Like several island homes, Killeen’s residence is elevated on concrete pillars, safeguarding it from storm surges in an area that barely reaches 3 feet above sea level at its highest. However, everything around her home was affected by the floodwaters, and then by Milton’s fierce winds.

“Everything below was devastated, including my husband’s Porsche. It was terrifying,” Killeen recounted.

Weppner then brought Big Boy to a stop, allowing Killeen to climb down the ladder so she could walk off the island. Authorities had restricted vehicles from crossing the bridges for most of Thursday, yet permitted residents like Killeen and Maria Williams to make the crossing on foot to check on their homes.

Meanwhile, Williams and her husband spotted Weppner driving back down Midnight Pass Road and hurried to catch a ride to her house.

“My husband asked if I thought I could catch him, and I just kept running,” Williams explained, catching her breath.

Like most residents, they had evacuated during Hurricane Milton. They had just finished removing drywall damaged by Helene when Milton hit. Many residents had done the same, piling debris from Helene outside their homes, awaiting pickup. Milton’s winds and lesser storm surge sent this debris scattering across the island.

“This was the last thing I needed,” exclaimed Williams as she struggled to catch her breath while Weppner’s truck splashed through the water. “Oh my God, I can’t even bear to imagine what my house looks like.”

Weppner, who hails from the Sarasota area, mentioned that his insurance company doesn’t have a direct connection to residents of Siesta Key, but he views them as neighbors. He noted that many are in for a rude awakening as they grapple with insurance providers that have offered inexpensive but largely inadequate policies.

“They buy these low-cost policies, and when disaster strikes, they find they’re not protected, tearing apart families and wreaking havoc on their lives,” Weppner stated. “In insurance, you truly get what you pay for.”

The approach of insurers towards claims from homeowners affected by two hurricanes in such a short span remains uncertain.

Helene caused significant destruction, giving Milton’s wind and water a chance to inflict even more harm. Unfortunately, many residents along the coast don’t have insurance due to its high costs.

Weppner pointed out that with expensive insurance, the alternative is losing everything.

“It’s sheer destruction,” he lamented. “Many people are just not ready for this.”

For numerous Floridians who have endured the aftermath of Helene and now Milton, there’s an increasing feeling of frustration and distress, as Milton adds to the havoc that Helene wreaked.

Businesses on the island, including Captain Curt’s Crab & Oyster Bar and the Crescent Club, are now facing an unexpected hurdle just before the busy tourist season begins.

While trying to get to her home near Midnight Pass, Williams pushed through fallen branches, with the sound of chainsaws filling the air. Water from Heron Lagoon had seeped into their backyard, although the inside of the house only had a small amount of water on the floors, with the bare studs exposed where workers had recently removed the drywall.

As she contemplated the difficulties of rebuilding, frustration began to show in Williams’ voice.

“I’m about to lose my (temper),” she expressed, substituting a different term. “I just wish the entire house would simply wash away.”

Back at his truck, Weppner expressed satisfaction in helping those he didn’t know. He mentioned that this is what makes America special: ordinary people supporting one another during tough times. He believes his truck can significantly improve someone’s day.

“Not everyone has the tools to handle situations like this,” Weppner shared. “If you can lend a hand, you should.”

With a grin, he added: “Driving it is also quite enjoyable.”