As legendary coach Joe Restic and the Harvard football team began preparations for the 1974 season, uncertainty abounded. After the departure of All-Ivy quarterback Jim Stoeckel ’74, the team was forced to rely on the wiry frame of untested senior Milt Holt, an eccentric southpaw signal-caller with almost no varsity experience.

Affectionately dubbed “Pineapple Milt” in honor of his home state of Hawaii, Holt had best been known around campus as a baseball player, the ace of the Crimson staff and a reigning First Team All-New England selection. Suddenly, he faced the tough task of leading a rebuilding squad still seething from its disastrous 35-0 drubbing in New Haven in the previous season’s finale.

For Holt, the test would prove to be the first gentle breeze of a violent whirlwind that would define his life both at Harvard and beyond.

Hero of the Game

Holt was known to be a wild card, a whimsical character who was reported to have once left the bullpen during a Crimson baseball game in order to fetch his transistor radio. Always a Hawaiian first, he would frequently wear Bermuda shorts and sandals around the Square regardless of weather conditions, and he generally tended to be almost too relaxed for comfort.

“Milt could be the most exciting quarterback we’ve had here,” Restic once told the Harvard Football News of Holt’s unpredictable nature. “And I mean that both ways—he can be very good or very bad.”

But despite the doubts of the media, the fans and even his own coach, Holt would more than hold his own as a starter. After struggling in a disappointing 24-21 loss to Rutgers in the season’s second game, he bounced back to lead the Crimson to a 5-1 Ivy record, affording his team a shot at a share of the Ivy title against unbeaten Yale.

The 1974 Game would come to be known as one of the best ever, even before a ball was snapped. Besides its championship implications, the Game featured an unprecedented three future NFL players—Harvard receiver Pat McInally ’75, offensive tackle Dan Jiggetts ’76 and Eli receiver Gary Fencik.

Furthermore, the Bulldog squad that visited the Stadium that November was perhaps their strongest ever, and one that was all too aware of the 29-29 “loss” suffered the last time a Yale team had come to Cambridge unbeaten, six seasons earlier. The Elis had blown through their competition, allowing only 46 total points in cruising to an 8-0 record. Only Penn had mustered more than ten points against Yale’s dominating defense, and an amazing six Bulldog opponents had been held to a touchdown or less.

But of all the players to have worn the crimson and white, Holt was perhaps the one least likely to be affected by any such numbers.

And when the Game finally came around, he displayed his trademark composure and confidence in dramatic fashion. Trailing 16-14 with just over five minutes left, Holt faced 90 yards between him and victory, with one of the toughest defenses in league history standing in his way. Still remarkably unfazed, Holt calmly led his team into the closed end of the Stadium, managing the clock masterfully as he converted clutch play after clutch play.

Finally, with 15 seconds on the clock and the ball lying on the Yale one-half yard line, Restic called timeout. But rather than send out the field goal unit to get the win and the share of the Ivy title, he showed the ultimate confidence in his rookie quarterback, keeping the ball in his hands. Pineapple Milt did his coach proud, running around left end and diving into the end zone for a touchdown that put Harvard on top for good—and ruined a stunned Yale’s unbeaten season.

The 14-play, 90-yard drive was the stuff of instant legend, even prompting Harvard “News and Views” journalist Will Cloney ’33 to write—admittedly in a moment of hyperbole—that “[the 1974 Game] wasn’t just as good as the 29-29 thriller in 1968. It was better!”

With his 212-yard, two-touchdown passing day, Holt had cemented himself as the Crimson’s single-season record-holder both in passing yards, with 1,351, and passing touchdowns with 16. In just one season, Holt had catapulted himself from career backup to All-Ivy quarterback, an amazing ascent that would ultimately land him in the Harvard Varsity Club Hall of Fame.

Though his yards mark has since been obliterated by more than a dozen pass-happy Crimson signal callers, his standard for touchdowns is still good for No. 3 all-time, and “The Drive” has become a fixture in Harvard-Yale lore.

But unbeknownst to Holt at the time, his accomplishments in the Game would soon become only a footnote in the anthology of his adventurous life.

Hawaiian Pinched

After graduation, Holt returned home to Honolulu to embark on his post-Harvard career. By 1978, the 26-year old prodigy had already been elected to the Hawaii state legislature as a state representative. Despite his youth, many were already predicting that the democratic Holt would one day become governor of the island state.

And indeed, it seemed that Holt’s supporters were onto something. Using his guile and skill in political maneuvering, he quickly became one of the most respected and powerful figures in Hawaii, holding a long-standing position as a state senator and ultimately rising to Vice President of the state senate.

“He had everything,” long-time friend and Honolulu City Councilman Mufi Hannemann told the Honolulu Star-Bulletin. “He had education. He had background, He had charisma. He was destined.”

But even as Holt approached the top of the world, he teetered dangerously close to the abyss. His marriage slowly deteriorating, he found his once-charming eccentricity manifesting itself in ugly ways. Holt struggled with crises in his personal and family life, beginning a self-described process of “drifting” from his previously stable home life and career.

He soon entered an excruciating downward spiral of which many were unaware and others were powerless to stop. He became addicted to crystal methamphetamine, spent an increasing amount of time in casinos and strip joints, and endured several minor scrapes with the law. Each incident served to gradually erode his political credibility and widen the already considerable rift with his family.

Several financial scandals soon dealt the final blows to Holt’s political career. Amid speculation that he had diverted over $20,000 from the Bishop Estate—a trust intended to fund local schools of which he was a trustee—for personal use, including colossal tabs at various late-night entertainment and dining spots, Holt suffered a crushing loss in his 1996 bid for re-election.

By 1999, Holt had bottomed out. Facing charges not only for the so-called “Broken Trust” scandal with the Bishop Estate, but also in connection with mismanagement of campaign funds from his 1996 run for the senate, he suddenly found himself facing up to five years in prison. He had little choice but to agree to a plea bargain, accepting guilt on one count of mail fraud for using campaign money for personal expenses.

Holt was sentenced to one year in federal prison, a term that was later shortened by four months due to time served for drug-related charges. Quite simply, Holt’s downward spiral was complete.

“Once praised for his brilliance and political potential, Holt has come to epitomize a fall from grace,” the Honolulu Star-Bulletin wrote in an editorial. “A rebound will not come easy for him.”

Time to Rebuild

Indeed, it has been a long road back for the Honolulu native. Since his release from prison in June 2000, Holt has worked with his three teenage boys at repairing the palpable damage in his family life. Now in the second year of a scheduled three-year period of supervised release, he has begun the long process of patching his sober life back together.

While Holt is still reluctant to speak with the media, indications from sources close to him are that he is well on his way to reclaiming at least his pride, if not his political power.

Nevertheless, if current Hawaiian quarterback Neil Rose—who already owns both single-season records that Holt once held—finds himself leading the Crimson into the closed end of the Stadium in the waning moments of Saturday’s Game, he may want to stop and think twice about the path he’s on. We’ve seen where it leads.