First he was denied a diploma and kicked out of the Naval Academy six weeks before graduation because he failed a running test by 20 seconds.
Then he was offered a dubious opportunity for re-admission: He would need to divorce his wife to meet the academy's requirement that midshipmen be single.
This week, Frank Shannon learned that the appeal of expulsion he sent to the Navy secretary three months ago has apparently been lost. And he received correspondence from the Navy threatening to garnishee his wages to recover $127,000 it says he owes in repayment of his incomplete education.
"It's kind of shocking, all of this over a 20-second run," he said. "I've tried to digest this and interpret what can actually happen and it doesn't add up. ... The wheels keep spinning."
Shannon is an unlikely candidate for such an odyssey. He was class president, a member of the National Honor Society and a blue-chip offensive lineman at Eastern Technical High School in Essex when he applied to the academy.
Standing 6 feet 3 inches tall and weighing 245 pounds, Shannon turned down several football scholarships to enlist in the Navy after the academy rejected him. He spent two years as a sailor, then one more at a prep school before he finally got in.
Shannon is the first to admit that the physical rigors of academy life were tough on him.
He failed his biannual physical fitness test 12 of 18 times. He could handle the push-up and sit-up tests. But the distance run - where Mids have to cover 1.5 miles in 10 minutes and 30 seconds or less - killed him.
Shannon was put in a remedial program to help him meet the requirements, and always passed with coaching from friends, until the final test of his fall semester of 2005.
After failing several consecutive tests, the academy kicked him out. His final time was 10 minutes, 50 seconds.
With no commission, Shannon and his fiancee, Gloria Mangano, gave up their plan to wed June 10 at the academy chapel. Instead, they got married at a local church.
And instead of beginning his career as an ensign on the USS James E. Williams in Norfolk, Va., Shannon took a job at a home improvement store.
But shortly after The Sun published an article about Shannon in May, he was contacted by Joel Meredith, general manager of Siemens Building Technologies' Baltimore office.
Outraged by Shannon's story, and impressed that the former midshipman was an Eagle Scout, Meredith hired him as an apprentice engineer, the same job he could have had if he had received his degree.
"When I read the article, I was on a train headed to Washington for a Boy Scouts meeting," Meredith said. "I could see that it was somewhat ridiculous what happened to him."
While his job in a field with promising earning power has made things easier, the looming $127,000 debt - the Navy demands repayment of educational costs when a midshipmen is expelled - prevented the Shannons from securing a loan to buy a three-bedroom home in White Marsh. Now, they live in one bedroom at his in-laws' home in Baltimore County.
Shannon turned for help to the office of Sen. Barbara A. Mikulski, a Maryland Democrat who sits on the academy's Board of Visitors, for help. Through a spokeswoman, Mikulski declined to comment for this article.
Admission to the academy generally requires nomination by a member of Congress, and the education is free as long as the midshipman graduates and fulfills a five-year service requirement.
A Mikulski aide contacted Shannon's mother, Susan Schaub, in October, encouraging him to reapply and hinting that it would be worth his while, Shannon and his mother said.
In a later e-mail, however, the aide, Celeste Hughes, suggested Schaub check with the academy "about the marriage issue. It may be a disqualifier, after all, and I would hate for Frank to get too far down this road before knowing for sure."
Midshipmen are not allowed to be married. And, according to Maryland law, Shannon would have to separate from his wife for a year before he could get a divorce, then reapply with no guarantee he would be able to return to the academy.
Outlandish as the idea was, he seriously considered it, consulting with his wife, Gloria, midshipmen and his mom before realizing that he would be pushing the academy's age limit of 27 by the time he graduated.
Family members said the fact he even thought about it showed how badly he wanted to finish at the academy.
Gloria Shannon even said she would have gone along with the divorce - if his readmission was a sure thing.
"But I'd be really [ticked] if we did all that for nothing. We sacrificed seven years of our lives, our potential future, so he could attend the academy and achieve his dream," she said. "Is it really worth risking it for people who are willing to sacrifice someone for 20 seconds?"
Instead, Shannon pinned his hopes on the Pentagon.
In September, the Defense Department notified him that he must repay the debt in installments of almost $4,000 a month for three years. Shannon did not send any checks in hopes that Navy Secretary Donald C. Winter would overturn his expulsion.
He had written the secretary in August to appeal his expulsion - and repayment of his education - and retained a receipt of the certified mailing, which he showed The Sun.
Computerized tracking records by the U.S. Postal Service show the letter arrived at the Pentagon post office on Aug. 10.
A Navy spokesman said yesterday, however, that there is no record of that letter being received in the Navy secretary's office.
Shannon also received a letter this week from the Defense Finance and Accounting Service saying he is in default on his repayment schedule and faces being referred to a collection agency. He could have his wages garnisheed and tax refunds seized, the letter said.
Shannon is consulting with an attorney about whether to re-send his appeal request. "I'll probably send it again and hope for the best," he said.
The academy's hard-line stance with Shannon stands in stark contrast to its treatment of seven Navy football players who admitted using steroids in early 2005.
As revealed last week in The Sun, the athletes were restricted to their dorms for several weeks, a punishment normally reserved for minor conduct offenses. Only the two players caught through urinalysis tests administered by the National Collegiate Athletic Association were barred from playing in 2005, as required by the NCAA.
In a May interview with The Sun, Col. David Fuquea, who handled the internal disciplinary process for the seven football players, defended the academy's handling of Shannon's case, arguing that all midshipmen at the Annapolis military college are treated equally.
"This institution is responsible for training graduates who immediately will be committed to the global war on terror," he said at the time. "We cannot afford to send someone out to lead sailors and Marines that has not met the standard morally, mentally and physically."
Fuquea, now the deputy athletic director, and Vice Adm. Rodney P. Rempt, academy superintendent, declined to be interviewed for this article. An academy spokesman said that Fuquea stands by his earlier comments.
Asked to compare the steroid cases to Shannon's, the academy issued a statement: "These are completely different cases with completely different facts and circumstances."
Gloria Shannon scoffed at the academy's reasoning.
"If the academy holds a higher standard than everybody else, why is 20 seconds more important than using illegal drugs?" she asked. "I'd rather have someone who can't run as well as someone else, but at least they're honorable and don't lie, cheat or steal."