When Rich Davey walked through the Metropolitan Transportation Authority’s foyer for the last time as the agency’s NYC Transit president, the crowd that greeted him included a staffer who held up a sign that read “BOSTON SUCKS.” An addendum in smaller print followed: “Davey OK.”
Amid the blaring of the bagpipers who were part of the send-off, Davey laughed, and made his way to the exit, with his security detail in tow. “A former cop, but yeah, they didn’t tell me that until after I said yes to the job,” Davey said, recalling the moment as he slid into a booth at the Trident bookstore and cafe, located just around the corner from his Back Bay apartment.
“Thankfully, there’s a little more anonymity in this role,” Davey added. He had just hit the one-year mark in the top job at Massport, the quasi-public agency that runs Logan International Airport and the terminals of the Port of Boston.
“The beauty about Massport is there’s sort of the day-to-day operations, like, why can’t we get the bags to baggage claim more quickly?” Davey told me. “But you also have the mindshare to think big and think strategically. And some of the roles I’ve had, it’s been much more blocking and tackling the day-to-day, particularly at New York City Transit.”
Davey, as well as his media relations director Jennifer Mehigan, joined me at Trident to talk about his career, the high school classmate now running Immigration and Customs Enforcement (ICE), and whether he harbors any political ambitions. Davey ordered the scrambled egg special, with an English muffin, while I went for the smoked salmon and eggs and Mehigan got the frittata.
Davey has held a variety of transportation sector jobs over his career and he is known for his sense of humor. He needed it while working on the ill-fated Boston bid for the 2024 Olympics. (“My therapist says I don’t have to talk about that,” he joked.)
In 2023, Tom Glynn reached out to Davey about the Massport CEO job as Lisa Wieland geared up to leave the position. They knew each other from when Glynn served as Massport CEO in the early 2010s and Davey was Massachusetts transportation secretary, chairing the agency’s board. Davey raised the issue of timing: By that point, he had been in New York for a little over a year, and he wanted to stay for at least two.
He also considered the MTA post “transit royalty,” and he had left behind consulting to take it. While in the job, he ended up sparring with Whoopi Goldberg, Andrew Cuomo and several members of Congress over congestion pricing.
“I’ve seen the data. It’s working,” he said. Asked whether it could work here, he said engineers could possibly figure it out, but Manhattan was less complicated. “Manhattan is an island. It’s very easy to corner off and restrict the traffic.”
Since NYC Transit oversees both the subway and buses, he also chased after drivers illegally parked in bus lanes. It’s easy to picture if you remember the famous moment from his tenure as MBTA general manager, when he was spotted on camera trying to stop a fare evader.
Logan Airport, where he did end up landing after a recruiter reached out, doesn’t offer an easy villain. “I was sitting at the Cape Air gate a couple weeks ago – we were supposed to fly to the Vineyard and the trip got cancelled because of weather – but I had a lot of feedback about the sad gate that is Cape Air and some furniture we need to improve, some other stuff,” he said. “That’s what I love about the job, to block, tackle and improve that experience, but also think big, like remote terminals and blue tech.”
A “remote terminal” would allow for passengers to check in and get screened at offsite parking locations, such as Framingham, Back Bay and Braintree. (The Braintree parking site used to be a drive-in theatre, where a young Davey, who grew up in Randolph, saw “Raiders of the Lost Ark.”)
“I think one of the reasons why the [Massport] board hired me is not because I’m an aviation expert. I’m a ground transportation expert,” he said. “That’s the challenge at Logan Airport. You know, we have gates, runways. The air side of the airport has been invested in, well-managed, and we have opportunities to add more flights, if we want to. Airlines are bringing in bigger planes, quieter planes, actually, so we’re able to add more passengers. But how do you get them there? No one’s building a third or fourth tunnel anytime soon.”
At this point, because I’m shamelessly cribbing from the “Lunch with the Financial Times” format, I realized I must ask how he likes the food at Trident. While digging into his scrambled egg special, he recommended the tuna melt, since he tries to avoid meat. “I’ve been coming here since I moved in,” he said. “My wife bought her condo in 2004, we got married in 2005, so I’ve lived in this neighborhood for 20 years.”
His wife is Jane Willis, the Ropes and Gray attorney who was once part of the famous blackjack team of Harvard and MIT students. (In the movie about the team, “21,” Kate Bosworth played a character based on Willis.) Willis and Davey met at a going-away party for someone else in June 2003. “She asked me out, by the way, for the record,” Davey quipped. “A Red Sox game. But I will say this, though: there were two other guys at the game, and I was like, ‘Wow, what is this?’ They were two of her good friends, and still are good friends today, but I wasn’t exactly sure what I was walking into that first date.” He kept the ticket stub and gave it to her a few years later as a gift, and it now hangs in their home.
Davey and Willis don’t have children, “so we’re pretty mobile, and she’s always been very supportive of whatever adventure I want to jump into,” he said. Taking the NYC transit job certainly qualified, as the system was coming out of the COVID-19 pandemic when he signed on.
His time at the MTA was not his first experience in New York. Davey’s first job out of law school was within the U.S. Justice Department, as a prosecutor for the Immigration and Naturalization Service.
He left INS after just two years, because “there were a couple of cases where I thought that the outcomes were wrong,” and he disagreed with the immigration laws. “I can only imagine today, they’re in absolute, desperate need of reform,” he said. “So it remains to be seen if that will happen.”
INS was succeeded by a variety of agencies, including ICE. An irony for Davey is that ICE’s acting director, Todd Lyons, is a former Boston College High School classmate. They were once close.
Asked whether he has spoken with Lyons about the current immigration climate, Davey said they’ve texted. “I really just checked in with him as a person. It’s not up to me or in my role to be providing feedback on what ICE is or isn’t doing. But look, I knew him as a 16-year-old goofball hanging out at the South Shore Plaza in Braintree back in the day.”
Davey added: “I know government service isn’t always easy, and what they’re going through right now sure as hell isn’t easy for a lot of people. Not only ICE, but also some of the folks that ICE is arresting or otherwise detaining. But I know him to be a good guy, so that’s why I reached out.”
The mention of government service reminded me I wanted to ask him about elected office. He was once floated as a candidate ahead of the 2013 race for mayor of Boston.
“No, I have put those ambitions long behind me, maybe two decades ago,” he told me. “I actually have found a lot more joy in appointed positions in government. And honestly, whenever my tenure’s up at Massport, hopefully that won’t be anytime soon. You know, I’m aware that I’m the first person to serve as the MBTA general manager, the CEO of Massport and the transportation secretary of Massachusetts. I hope that’s my contribution, improving transportation here.”