Reality Check: Jennifer Massey '96

The Apprentice 2 (2004)

The Apprentice originated in the United States and airs on NBC. Billed as “The Ultimate Job Interview,” 15 to 18 businessmen and businesswomen compete for a one-year, $250,000 job running one of Donald Trump’s companies. Each contestant performs a series of rigorous business tasks, many of which include prominent Fortune 500 companies and require street smarts and intelligence to conquer. At the end of each episode, the losing team is sent to the boardroom. Trump and his associates judge the job applicants on their performance of the task, and one person is fired and sent home. 

Editor’s note: Massey was not available for comment. The following article appeared in The Daily Princetonian Jan. 10, 2005. 

Massey ’96 handles competition in TV’s Apprentice II

By Eric Herschthal ’06

Jen Massey ’96 had a skiing trip to Mammoth, Calif., planned for last winter when dismal weather conditions compelled her to cancel the vacation. Instead, she chose to try her luck auditioning for the reality show “Apprentice II” in Hollywood.

Unlike most show applicants, Massey did not make an audition tape or sign up months in advance for her chance at television stardom. She showed up the day of the auditions empty-handed, bringing only her wits and ambition to impress billionaire developer Donald Trump.

After Massey made the cut to be on the show, she found herself having dinner with the real estate tycoon and several other show contestants.

“Apprentice II” selected 20 ambitious young professionals to vie for a one-year contract to work with Trump.

Massey said that Trump made reference to her college degrees.

According to Massey, after a long evening in the Trump Tower penthouse overlooking New York City, the businessman turned to her and said, “I’m very impressed with Princeton.”

Massey, who said she was bemused by the humility of a man characterized by pomp and ostentation, responded with a nod of agreement.

She said Trump told her the only school he was more impressed with was his alma mater, Wharton School of Business at the University of Pennsylvania. 

College years

After graduating from Princeton, Massey went to Harvard Law School.

She said she is well aware and proud of the advantages her degrees gave her on the show, on which she made it to the final round only to be “fired” on the last episode.

“The fact that I graduated from two of the world’s top institutions resonated with Trump,” she said. “Having schools like Princeton and Harvard on your resume opens up tons of doors.”

At Princeton, Massey majored in English with a certificate in Creative Writing.

One of only two students selected to write a creative senior thesis, she crafted a collection of short stories about life in the South, she said.

Massey was deeply involved in extracurriculars and academics at Princeton.

A member of the Honor Committee and the Mock Trial team, she graduated with honors from Phi Beta Kappa.

Socially, Massey was also very active.

She joined the sorority Kappa Alpha Theta, for which she served as president, and was a member of Cottage Club.

Caren Palese ’96, a classmate and good friend of Massey, said students were attracted to Massey’s “spunky” personality.

Since graduating from law school, Massey has worked for two law firms but has recently been hired as a legal analyst for Fox News Channel on a temporary basis. 

'Twisted view'

On the show, Massey was consistently portrayed as overly ambitious, aggressive and underhanded.

The episode that especially branded Massey required contestants to create a Levi Jeans catalog.

The contestants were placed in small teams to craft a brochure that advertised all of the lines of Levi denim.

The “Fit Wheel” — an innovation that matched jean style to size — was created by one of Massey’s team members, Ivana, a fact that Massey readily concedes.

But when the “Fit Wheel” was presented to Trump, Massey introduced the product without giving credit to Ivana. “We created the ‘Fit Wheel,’ ” Massey continually said in the episode, as Ivana was shown rolling her eyes in annoyance.

Massey said the fact that the team had chosen her to speak on its behalf was not aired on the episode.

“There were times where I felt the editing showed a twisted view of the events,” she said.

After that, “America did not embrace [Massey] as much as they might have by showing her in an angle that wasn’t right,” Palese said.

Even at Princeton, Palese described Massey as “the girl that everybody loves to hate.” She said she remembers looking on with awe as Massey won academic accolades with seemingly little effort.

But the combination of intelligence, ambition and sociability matched with good looks made Massey vulnerable to envy.

When looking at Massey “you would never know how intelligent and witty she is,” Palese said.

But that is what was so interesting about Massey, she said.

Massey has been successful both in and out of Princeton, without showing signs of the stress or dismay, she added.

For her part, Massey is dedicated to pursuing her a new career in business media.

“I don’t want to be one of those reality stars who tries to coast on their reality TV fame,” she said.

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