It was nearly 6 p.m. when Orion Lexington, a lanky dean’s list student at Northeastern, clambered aboard the E line trolley through the rear doors at Longwood, found a place in the crowded car, and ignored the conductor’s customary call for those without monthly passes to come forward and pay. Headphones on, Lexington settled in.

As the trolley rolled inbound, a woman in a windbreaker stepped forward, flashed a badge, and asked Lexington to tap his CharlieCard on a handheld computer to see whether he was a monthly passholder. This was Ann Garvey, an undercover officer and part of an effort by the MBTA to crack down on riders who do not pay the fare, at a time when the T boasts record ridership but is under financial pressure to raise prices and cut service.
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As a freeloader, Lexington was not alone - although a precise figure is difficult to calculate, the T estimates that tens of millions are lost annually through fare evasion. He was not even alone on this trolley. Half a dozen riders in the rear of that car Tuesday had boarded with no intention of paying. Garvey asked Lexington for an ID, preparing to write one of the 3,000 citations for $15 that the T issues annually.
Never removing his headphones, Lexington unleashed a salvo of protests: “This is my stop! I’m a newbie! I could just go pay! This is not fair! How is this fair? Look at this sea of people!’’
For years, riders like Lexington faced few repercussions for hopping turnstiles or boarding trolleys and buses without paying. Those caught had to pay the fare or face ejection; those resisting were occasionally arrested for disorderly conduct or trespassing. Most who rode for free got away with it.
Then lawmakers empowered Transit Police and some civilian employees to issue noncriminal citations, similar to parking tickets. But those $15 tickets have few teeth. Of exactly 10,500 written from January 2007 through Tuesday, nearly two-thirds remained unpaid.
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The T can issue expensive citations for repeat offenses - $100 for the second offense, $250 for all others - but those are rare. Officers in the field must call in to check names for past offenses - a time-consuming effort when a single crowded trolley can carry more evaders than a two-officer team can quickly ticket. Only nine repeat-offender citations have been issued in 2011.
And those who ignore their citations face no penalties and receive no reminders until a year has passed, when the T gives people another 90 days to pay up, appeal, or have their next license renewal blocked at the Registry of Motor Vehicles. But driver’s licenses expire only every five years, and many cited have no license - or, like Lexington, have licenses issued outside Massachusetts.
All of which means freeloaders have little incentive to stop, frustrating transit officials and police, and creating numerous scenes such as the one that played out on the E trolley Tuesday.
As Garvey persisted, Lexington, 20, pretended to forget his address and declined to produce his license until Garvey ushered him off at the Northeastern stop, where she and fellow Officer Stanley Pa’u - busy writing tickets to other fare evaders - could address him away from the crowd.
When Lexington finally complied, they issued him a $15 ticket and ran his license to check for outstanding warrants. It came back clean.
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“Really unfair,’’ he told a reporter afterward, tearing up his ticket. Like most, he had no intention of paying.
The losses the T incurs because of unpaid fares and fines, if recouped, would not be enough to pay off the T’s $6 billion debt or plug a projected $161 million deficit for the coming year. But officials said the losses are substantial and amount to stealing from people who pay to ride and who pay taxes. That is why the Massachusetts Bay Transportation Authority and the Legislature’s Joint Committee on Transportation are working on a bill to make fines more expensive and easier to enforce, state Secretary of Transportation Richard A. Davey said Thursday.
“It’s clear to me that we really need to provide the MBTA staff with more tools,’’ Davey said.
Davey said the bill, which will be filed in January and could take effect as early as July, would make fines comparable to those in New York, which jumped from $60 to $100 in 2008, with additional penalties for those who fail to pay up swiftly. The added revenue would more than offset the costs of pursuing offenders, Davey said. The bill also proposes to use the threat of criminal penalties to coerce scofflaws without Massachusetts licenses to pay fares and fines.
Paul Regan, executive director of the MBTA Advisory Board, said the T should be vigilant about fair evasion. “They need every single dime that they could possibly get,’’ said Regan, whose board represents cities and towns served by the T. It is also an issue of fairness, he said. “If you’re a paying customer and somebody tries to come in behind you through a turnstile or you see people riding for free, it burns you.’’
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But riders do not always side with the officers who are trying to bust fare evaders.
“The crowd will turn on you occasionally,’’ said Sergeant Kirk Donovan, who accompanied the undercover officers with a Globe reporter and photographer Tuesday.
Bystanders - who sometimes applaud or join in protest - kept mostly quiet that night that the officers declared themselves and a plainclothes inspector stepped forward to join them with a handheld pass-checking computer. A few scoffed, saying people should be forgiven or issued warnings.
“Is this the first time they’re doing this?’’ one man asked, looking up from a book. (The schedule varies, but the T does a handful of “compliance checks’’ a week, out of thousands of trips.)
In 90 minutes, Pa’u, Garvey, and Green Line inspector Maxine Bell issued 17 tickets. Most cooperated. Two 60-something sisters from Chelsea scolded the officers, saying they should be allowed to ride free because they came from the hospital. “I have five operations,’’ one said, enumerating her ailments. “For what, 35 cents you need to do that? We were going to pay.’’
Eric Moskowitz can be reached at emoskowitz@globe.com.