Why Should Delaware Care?
One of the highest costs for Delaware’s transportation department involves the land it must acquire for major infrastructure projects. A recent land sale brings into question DelDOT’s safeguards to ensure personal business interests don’t interfere with the process.
Following a Spotlight Delaware inquiry, Delaware Department of Transportation officials launched an internal investigation into a taxpayer-funded land deal that turned a million-dollar profit for a state transportation planner’s business partner.
In 2015, Four C’s Properties LLC, owned by businessman Charles Messina, bought a half acre of land off Route 1 near Lewes for $225,000.
Eight years later, the LLC sold it to DelDOT for $1.6 million – a seven-fold increase agreed to by the agency that also employs Messina’s business partner, Todd Sammons, as a chief planner.
Last month, Spotlight Delaware emailed DelDOT seeking details about the deal. In a response, agency spokesman C.R. McLeod said officials had opened an internal investigation into “claims of a business relationship influencing a property acquisition.”
Asked on Friday about the status of the inquiry, McLeod said, “The investigation is ongoing.”
McLeod declined to provide details about the investigation. But public records show that Messina owns a company, called SS Investments of Delaware, with Sammons, DelDOT’s assistant director of development coordination. The two appear to have been business partners since at least 2005, when they jointly sold a Kent County property.
While they are business partners through SS Investments, Spotlight Delaware did not find evidence that Sammons is part of Four C’s – the company that sold DelDOT the land off Route 1. Still, he did serve as a witness on a signed property record involving the company in 2023, suggesting that he is familiar with it and who owns it.

DelDOT bought the Lewes-area property in question from Four C’s in 2023 as part of a project to improve the Route 1 corridor between Minos Conaway Road and Tulip Drive – an area that sits amid a boom of new residential and commercial developments.
Transportation officials have said the project will transform the area’s vexing traffic congestion by extending several roads and connecting them with three new roundabouts.
One of the roundabouts and road extensions will be built directly on Messina’s former property. The project is currently under construction with an expected completion date of summer 2028.
DelDOT has considered building a road on that property since at least 2011, agency documents show. Sammons has worked for the agency since 1999, McLeod said.
Neither Sammons nor Messina responded to requests to comment for this story.

Past DelDOT land deals
In past years, DelDOT has sought to shed a stain on its reputation caused by questionable land deals.
One previous case occurred when the agency sold land for $270,000 to an influential lawyer and developer in 2018, a decade after it had purchased it for nearly $2.8 million.
The agency said at the time that the price reflected a DelDOT decree that the land would never gain a commercial turnoff from Route 1. Still, the deal attracted controversy, erupting in 2020 as a political attack on the state’s Democratic Party.
When asked last month about departmental safeguards in place today to avoid conflicts of interest, McLeod said DelDOT’s property acquisition process is “dictated by strict state/federal regulations.”
He said the agency uses private sector appraisers for any acquisitions anticipated to be valued at greater than $25,000, and sometimes even for properties below that threshold. Those appraisals are then independently reviewed and approved to ensure they meet state and federal requirements.
He said DelDOT followed the process before purchasing Messina’s property, which he noted was likely to be rezoned as commercial.
Was the price fair?
In the same year that DelDOT bought Messina’s property, the agency also purchased a similar half-acre piece of land across Route 1 for $203,800.
DelDOT will also build a roundabout on that property, which previously served as the parking lot for the Lewes Senior Activity Center.

Asked about that discrepancy in prices paid to Messina and to the senior center, McLeod said the size of the property does not always translate to its value. The price is also determined by the buildings that are on the property, he said.
Another 2023 DelDOT land purchase highlights the potential differences in the prices of seemingly similar properties. DelDOT bought a half-acre property just north of Messina’s for $1.8 million from Andrew Lewandowski, who bought it in 2014 for $235,000.
That property is zoned for commercial and residential use, while Messina’s former property is zoned for only residential and agricultural use.
Messina applied to rezone the property to allow for commercial use in 2018. The application remained pending until it was withdrawn in 2024.
Former DelDOT employee T. William Brockenbrough Jr. sent a letter to Sussex County in 2018 saying the agency was then trying to acquire the land for the Route 1 improvement project.
Brockenbrough added that the agency didn’t anticipate the rezoning application to significantly impact the value of the land because DelDOT was already appraising the land assuming its highest and best use as a commercial property.
Following state and federal regulations, DelDOT appraises properties to their “highest and best use,” McLeod said.
And the agency determined the highest and best use of Messina’s property was commercial because of the likelihood of a zoning change approval, he said.
The four criteria for the highest and best use are “the reasonably probable and legal use of vacant land or an improved property, which is physically possible, appropriately supported, financially feasible, and that results in the highest value,” according to the agency’s Right of Way Manual.
Timeline of events
- 2011: The earliest public document referencing Messina’s former property is a feasibility study dated January, 2011. The study looked into options for extending New Road onto Messina’s former property and connecting it to Route 1 using the existing bridge over the Lewes/Georgetown Bike Trail.
- 2015: Messina then bought the property in 2015 from Thomas Best & Sons Inc. for $225,000 through Four C’s Properties LLC. Representatives from Thomas Best & Sons did not respond to multiple requests for comment.
- 2015: Sammons in 2015 served as a project manager in the agency’s Division of Planning. McLeod, DelDOT’s spokesperson, said that division “does not have a role in the acquisition of specific properties.”
- 2018: Messina applied for the rezoning in 2018. DelDOT was already in the process of trying to acquire the land that same year, according to Brockenbrough’s letter.
- 2018: Sammons and Messina became joint members of SS Investments LLC in 2018. The company was originally created in 2004. An employee from SS Investments LLC did not respond to a request for comment.
- 2023 and beyond: DelDOT bought Messina’s land in 2023 for $1.6 million. The agency has since demolished the buildings on the property to clear the way for the extended road.

