Throughout his five decades of orbiting rock royalty and unsung legends, Tony Glover rarely bragged about his amazing adventures and prized possessions, even to his fellow musicians or avid music collectors.

So no wonder his wife of 28 years, Cynthia Nadler — who never shared her late husband’s deep passion for and knowledge of music — wasn’t hip to all the cool stuff stored in their St. Paul home.

“For years, I’d been telling Tony, ‘Maybe we should get rid of some of this junk,’ ” Nadler recalled, pausing on “junk.”

“I’m learning to call it ‘archival materials,’ instead,” she said.

Including personalized items from Bob Dylan, Jimi Hendrix, the Doors and Patti Smith, Glover’s lovingly stored clutter has turned into probably the most valuable personal collection of music memorabilia from Minnesota ever put up for auction.

Rolling Stone called the 169-piece bundle — up for bidding starting Thursday — an “extraordinary time machine.” RR Auction of Boston, which has overseen sell-offs of Prince, Elvis and Beatles collections, set the starting price at $250,000.

At the center of the auction are many hours of recorded interviews, early performance tapes and handwritten correspondence with Dylan, including letters, postcards and signed gig fliers from the early 1960s.

Glover, who died in June 2019 at age 79, befriended in 1960 the Dinkytown hanger-on from Hibbing and helped teach him harmonica and Woody Guthrie tunes. They stayed friends after Bob left for New York, and they even went together to see Guthrie in the hospital there.

When he became a writer for Rolling Stone, Creem and other magazines later that decade, Glover had access to the enigmatic music legend that few other music scribes ever enjoyed.

“Tony saw his transformation into Bob Dylan and was there for many of the pivotal moments,” said Bobby Livingston, RR Auction executive vice president. “Bob clearly respected him and put a lot of trust in him.”

Glover was also a meticulous collector and archivist. His neighbor and close friend Pete Lee, longtime KFAI radio DJ, described how a passing mention of an old interview or magazine clipping would end with “Tony going to some drawer or box and finding it within a minute or two.”

“He didn’t collect all this stuff to capitalize on it,” Lee said. “He did it because that’s who he was: a rabid collector.”

Familiar handwriting

Nadler wasn’t naive about the value of, say, her husband’s ultra-rare autographed copy of a Jim Morrison poetry book. She just did not know how much of it there really was — not until Livingston flew to town to comb through it all and gained her trust in the process.

“He started talking about a bunch of obscure blues harp players,” Nadler recounted. “I thought, ‘OK, Tony might’ve liked this guy.’ ”

The big wow for Livingston was discovering pages of typed interview transcripts stored in a drawer with familiar handwriting he’d seen on other hot auction items over the years.

“I recognized it right away, and thank God I did,” said Livingston. “It might’ve been mistaken for unimportant papers.”

Dylan himself had written changes and comments all over the transcripts, editing his own interviews.

The rather revelatory transcripts — intended for Esquire but never published — are a big enough deal for renowned historian Douglas Brinkley to write a lengthy article about them for Rolling Stone.

“[Dylan] was untroubled and erudite, willing to shed light on things he’d never fully explained before,” Brinkley wrote.

And while the Dylan items have grabbed all the attention, they make up only about a third of the total RR Auction lot.

Other highlights include: interview and concert recordings from Jimi Hendrix’s 1968 gig at the Minneapolis Auditorium; various Allman Brothers tapes (Glover wrote the liner notes to a Duane Allman anthology); handwritten Joan Baez and Pete Seeger letters; and many rare LPs and other items from Guthrie and blues legends such as Sonny Boy Williamson, Howlin’ Wolf and Little Walter (who Glover co-wrote a biography about).

Lee said the collection “helps tell the overall picture. ... There was so much more to Tony than just being a footnote in the latest Bob Dylan biography.”

Museums vs. collectors

One of Nadler’s main goals in selling her husband’s collection was simply to downsize. She sold their St. Paul home earlier this year and is currently snow-birding in an RV in Arizona.

She also liked the idea of putting her late husband’s work and treasures in the hands of historians and other collectors who could “appreciate it as much as he did.”

It’s not about the money, she insisted.

“I’ve been so busy just dealing with everything, I haven’t even had time to think about” the money, she said, pledging to donate some of it to music-related charities.

Nadler admits that she “worried about ruffling some people’s feathers.” In the case of Patti Smith, for instance, she said she opted not to sell some of Tony’s more personal items (including many hours of interviews) because “they had such a close friendship.”

For Dylan, though, she took cues from the man himself.

Dylan sold his own massive archive for more than $10 million to the Bob Dylan Center in Tulsa, Okla., which is due to open next year near the already established Woody Guthrie Center.

Nadler also pointed to Dylan’s approval of a previous auction by his early-’60s girlfriend Suze Rotolo (from the “Freewheelin’ Bob Dylan” album cover): “I figured if he’s OK with an old girlfriend selling letters, he’s not going to have a problem with this.”

RR Auction’s Livingston said Dylan’s management knows about the auction and has not gotten involved. Same with the Dylan Center in Tulsa, which expressed interest but wasn’t willing or able to pay close attention to auction prices, he said.

Lee believes his late friend “wouldn’t have wanted to see all this stuff filed away somewhere in the basement of a history center.”

Another longtime friend and fellow Dylanophile, former Treehouse Records store owner Mark Trehus, wishes at least some of these items would wind up in museums, but that’s partly because he truly believes they’re priceless.

“I don’t know what these letters and tapes will sell for,” Trehus said, “but rich Dylan fans should certainly view these items as holy grails. Dylan let his guard down with Tony because he trusted him, and the evidence is clear.”

Nadler did hang onto some other items. In particular, she is still hoping to give a museum another allotment of cool stuff belonging to one more legendary, if not quite so famous music act: Koerner, Ray & Glover.

Glover’s old band with Spider John Koerner and the late Dave Ray — who recorded for Elektra Records and played the Newport Folk Festival in the 1960s — was known to have influenced the Beatles, Rolling Stones, Doors, Bonnie Raitt, Beck and Lucinda Williams. Glover also later made some albums with Ray that gained a cult following.

Nadler believes this auction underscores her husband’s influence as a musician.

“I’m so thrilled his name is getting out there because of this, and he’s being recognized for who he was,” she said. “He was always seen as a musician’s musician, and the public didn’t know that as well.

“This says who Tony really was, at least to a certain point.”