When Bosun Odeniyi bought a taxi certificate in 1990, it meant freedom. Freedom from waiting for hours at the garage to pick up a car, from the ever-present leasing fees, and from not knowing whether a cab would even be available to drive.

In 2016, the taxi certificate - now called a medallion - is certified dead weight.

The medallion was long considered an ironclad investment, hitting its peak price at $545,000 in July 2014.

But UberX came to Philadelphia in October of that year, sending a chill through the industry even before it arrived.

Also that year, the Philadelphia Parking Authority opened bidding on the first new medallions to be sold in 14 years. It failed in August to open bidding at $475,000 and failed again in December at $350,000. The PPA finally dropped the minimum bidding price to $50,000 in March 2015, and successfully sold 30 of 61 wheelchair-accessible WAV medallions.

In October, the PPA plans to open bidding on 41 more WAV medallions, starting at just $10,000.

Odeniyi and other medallion owners say the rise of such ride-sharing services as Uber has left their investments underwater and their futures uncertain.

Nowadays, Odeniyi said, "You'd be lucky to see someone flagging you down because everyone has the apps waiting for Uber."

He says he used to make more than $100 in a single 12-hour shift, taking about 15 to 18 rides. Now, he takes about six to eight rides in a day, and if he can make $70 to $80 in that time, he's "doing great."

Since coming to Philadelphia without regulatory approval in October 2014, Uber has pulled the safety net out from under taxi drivers and claimed their place in the city. In the Philadelphia metro area, Uber says, it now has more than 12,000 active drivers - who have taken a ride in the last 28 days - and more than half a million active riders who have used the app in the last three months. In July, Uber pledged $2.5 million to expand its service in the suburbs and subsidize surge pricing, those times when prices jump for passengers in high-demand areas. This came after SEPTA announced that a third of its Regional Rail cars would be off the tracks for the summer due to fatigue cracks in a beam and the need for emergency repairs.

For a while, the PPA tried to keep Uber at bay, refusing to legalize UberX, which allows drivers to use their own cars and personal insurance to shuttle passengers.

But in July, with the Democratic National Convention bringing in 50,000 visitors and SEPTA's Regional Rail line in turmoil, the PPA conceded to Uber. It agreed to legalize UberX as long as the company paid $350,000 - rather than about $700,000 in fines it had initially slapped on the company - when the state legislature comes back in session and passes regulatory legislation.

At 57, Odeniyi had hoped to retire in a couple of years, having worked in the taxi business since 1983. But Uber has altered his plan. He bought his certificate in 1990 for $14,500, which he paid for over two years, he said. When his two kids - now fully grown and Ivy League-educated - were still in school, the business helped him be both career man and dad.

But if he were to retire now, Odeniyi said, he'd end up in line at a soup kitchen.

Uber's legalization was a blow to the taxi industry, not only because of increased competition, but also because taxis are subject to regulations that Uber isn't. Each year, medallion owners must pay an assessment fee, which was $1,819 per cab in fiscal year 2017 (up from $1,721 in 2016). Twice a year, cabs need to be inspected for $75 to $100 each time, depending on milage and type of car. It costs $125 each year to apply to renew a driver's certificate. Not to mention commercial insurance, which ranges from $5,000 to $7,000 annually, the PPA says.

For UberX drivers? All it takes is whatever they pay for their personal car insurance, assuming they also have a smartphone and model year 2001 car or later, spokesman Craig Ewer said.

"We're stuck in handcuffs of older technology with older regulations that essentially don't allow us to fairly compete," said Brett Berman, a lawyer who represents Freedom Taxi and Germantown Cab Co.

But the onus is now on the taxi industry to improve service, said Bruce Schaller, a transportation consultant who previously worked for the New York City Taxi and Limousine Commission.

Taxi workers "have been raised and worked for decades in a highly regulated environment, and they've adapted to that environment," he said. "It's like putting a polar bear in the Caribbean: Is it the polar bear's fault that it isn't doing so well here?"

"If I owned a medallion, I would have sold it last year," Schaller added.

But several taxi medallion owners are still holding out. Not that they have much of a choice. "They want to walk away, but they just can't," said Ronald Blount, a driver who heads the Taxi Workers Alliance of Pennsylvania. Owners "can't sell them because they owe more than the medallion is worth."

Still, Shawn Shojaian, who owns 13 medallions that he bought between 1983 and the early 2000s, said he's "holding out."

"I'm thinking about [how] Uber cannot survive because whatever they do, they're cheating right now," he said.

By "cheating," Shojaian means Uber's surge pricing model, which raises prices in areas of high demand to encourage its drivers to get on the road.

Taxis, on the other hand, are required to charge a standard fare of $2.70 for the first 1/10 of a mile and $0.23 for each 1/10 mile or 37.6 seconds wait time, and have exclusive street hailing rights.

In a statement, Uber defended its model: "By raising fares when demand in a given area outstrips the number of vehicles available, dynamic pricing incentivizes drivers to head to those places and meet that demand. It also gives riders who don't need a ride that very moment a chance to wait for prices to drop. The majority of a surged fare goes directly to the driver, and riders are given the exact price they will pay before they request the ride."

Shojaian said he has recently been charging drivers about $325 to $350 a week to lease the medallions. As of six months ago, he was charging $475 and had hoped to raise it to at least $500, but drivers complained that they don't make enough money anymore, he said.

Experts expect the taxi industry to become less regulated. Schaller and Queens College economist David Gabel, who has studied the impact of Uber on the New York taxi industry, both say that the deregulation of airlines in the late 1970s is similar to what taxis are experiencing today.

Airlines also used to have standard, government-regulated routes and prices like taxis. But free-market advocates won out.

This means taxi veterans may need to let go of the idea that they enjoy unlimited government protection. While Schaller says it will be hard for those ingrained in the system to catch up with the times, new investors can shake up the business.

"Like any industry that goes down, down, down," Schaller said, "at some point, someone will see opportunity there."

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