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While crossing state lines is considered a trip for most people, crossing from Oregon to California was something Max Greenfield did regularly. In March 2018, the then-25-year-old was living with his mother Andrea in Brookings, Oregon, his sister Tonya Brown told Dateline, and liked to go to the Lucky 7 Casino just across the border in Smith River, California.

Max Greenfield Tonya Brown

“It’s literally the only place around here that’s open 24/7,” Tonya told Dateline about the casino. Tonya says she is “exceptionally close” with Max and saw him all the time. The weekend of March 16, 2018 was no exception -- they began it by having a drink together on Friday night at the casino.

Tonya told Dateline she then dropped Max off at their mother’s house. Their mother Andrea would later tell police she saw Max at home the next day, Saturday, March 17. According to Tonya, Max has a medical condition, and their mother would routinely leave his medication on the counter at night so he would remember to take it in the morning. After saying goodnight to Max around 10:00 p.m. on Saturday night, Andrea laid the medicine out, as usual.

Tonya told Dateline that when their mother left for work around 6:00 a.m. on Sunday morning, the medication was still on the counter, which wasn’t surprising, since she wouldn’t have expected Max to be awake yet. Later that morning, Tonya began messaging Max to check in about previously scheduled plans to go to the movies together, but got no response.

“I was starting to get frustrated,” Tonya told Dateline. “Then, my mom got off work around 2:00 p.m. and called me because Max’s medicine was still sitting [at the house]. We thought that was very weird, and started making phone calls to see if anyone knew where he was.”

Max Greenfield with his mother, Andrea Greenfield. Tonya Brown

Tonya says that nobody knew where her younger brother was. Two days later, Max’s mother Andrea reported her son missing to the Curry County Sheriff’s Office.

There had still been no sign of, or word from, Max, but authorities were soon able to begin to piece together some of what he was doing on the night of Saturday, March 17.

Authorities learned through interviews with friends that, after saying goodnight to his mother Andrea around 10:00 p.m., Max had begun messaging people on his phone’s Facebook Messenger app, asking if someone could give him a ride to the Lucky 7 Casino. Family told Dateline that Max’s phone wasn’t connected to a phone number, so Wi-Fi-enabled messaging such as Facebook Messenger was his primary method of communication.

Authorities told Dateline that Max’s friends came to his house that night to pick him up and take him to the casino. Security footage provided by the casino shows Max arriving around 1:00 a.m. A Curry County Sheriff’s Office press release says Max is then seen going outside the casino and waiting near the back door.

“At approximately 1:50 a.m., Max Greenfield walks around to the front of the casino and meets up with a white male adult and they talk for several minutes,” the press release says. “Max Greenfield and the male are then seen walking south across the parking lot, parallel to Highway 101, until they go off camera, still walking south. This is the last location and time that Max Greenfield is known to have been seen.”

The casino is in Del Norte County, so the Curry County investigators handed the case over to the Del Norte County Sheriff’s Office once it was determined where Max was last seen.

“We started our investigation at that point,” Detective Jerrin Gill of the Del Norte County Sheriff’s Office told Dateline. “We were able to locate the guy [on the security footage] and bring him in for an interview. We’ve had a few interviews with him.”

Detective Gill said the man who Max walked off with is seen re-entering the casino, alone, 18 minutes later. In a statement to authorities, the man said he and Max “went separate ways after leaving the casino.”

“Max’s cell phone was Wi-Fi only, so it had no data,” Detective Gill said, explaining that that means they couldn’t use cell phone towers to track his movements after leaving the casino. Authorities were able to find, though, that Max’s phone never re-connected to Wi-Fi after it disconnected from the casino’s Wi-Fi.

“Whatever happened to him, happened soon after leaving the casino,” Detective Gill said.

Detective Gill said authorities have also talked to the people who drove Max to the casino that night, as well as people they learned Max was supposed to meet up with that night. Detective Gill declined to name these people to protect the integrity of the case.

“We’ve also done a ton of searches. I couldn’t tell you the amount of hours that have gone into this,” Detective Gill said. “We’ve brought cadaver dogs out at least a dozen different days.”

Despite their searches, authorities and family have yet to find anything belonging to Max. Detective Gill said this is particularly strange because Max is last seen on the surveillance footage carrying a large black duffel bag. His sister Tonya says Max takes his black duffel bag, filled with art supplies, everywhere he goes.

“You would think some of his stuff would be found, but we haven’t found any of it,” Detective Gill told Dateline.

“He didn’t have his I.D., his favorite jacket or his food stamp card,” Tonya said. “He’s never not talked to us for more than 36 hours in his entire life. If he gets stuck, he calls me or he calls our mom,” through the Facebook Messenger app.

Detective Gill told Dateline authorities have also conducted numerous search warrants as part of this investigation. He would not detail what those search warrants were for, but did confirm that none of them was for the residence of the man with whom Max was last seen.

“We definitely believe there is foul play involved,” he said. “We believe there are several people involved who have knowledge but may not be giving it up to us.”

Max Greenfield walking his sister Tonya Brown down the aisle at her wedding. Tonya Brown

Max’s sister Tonya told Dateline she also believes people know more than they are saying.

“I have a really hard time believing that nobody seems to know what happened that night,” she said. “None of it makes sense.”

“This is a pretty unusual and individual case. This is very unusual, because we don’t have, necessarily, anything that happened ahead of time that would lead to this,” Detective Gill said.

Max’s sister Tonya says the family is offering a $5,000 reward for anyone who can lead to Max’s exact location. She says she no longer believes her brother is still alive.

“It is a missing person’s case but we’re definitely treating it as a homicide,” Detective Gill told Dateline. “We’re putting all of our efforts into this case to try to solve it.”

Max Greenfield is described as a white male adult who is about 6’0” tall and weighs about 160 lbs. He has brown hair, blue eyes and a skeleton key tattoo on his left forearm. Max was last seen wearing black jeans, a dark colored t-shirt, a black jacket and a black beanie. He was also seen carrying his black duffel bag. If you have any information on Max’s case, please call Detective Jerrin Gill at (707) 465-2468.