George W. Bush wasn’t the only president who painted.

Rarely seen and never exhibited watercolors by John F. Kennedy, made while on the campaign trail in Brooklyn in 1960, are headed to auction as part of one of the most comprehensive collections of memorabilia dedicated to the late president ever assembled. The two paintings were gifted to a Beverly Hills-based socialite who donated generously to Kennedy’s campaign. They capture Marine Bridge at Sheepshead Bay, a testament to the president’s fondness for sailing, and are being offered as a pair with an estimate of $40,000. Accompanying photographs show Kennedy working at an easel, with his wife Jacqueline watching over his shoulder.

The entire trove, offered by the Boston-based RR Auction, consists of hundreds of objects spanning the president’s childhood as a student at Choate Academy all the way through his time as president. It was amassed by Ronnie Paloger, a California-based collector who at one point had an extensive collection of Muhammad Ali memorabilia, which he sold 1997 before turning to Kennedy’s wares.

Paloger spent years tracking down the JFK objects, which he hopes will be bought en masse and donated to the John F Kennedy Presidential Library and Museum, with bids for the collection expected to climb past $1.5 million. He said he wishes he could donate the collection himself, but the proceeds will fund his retirement.

John F. Kennedy’s senior year portrait at Choate, 1935. Courtesy of RR Auction.

A closely watched lot is the three-page handwritten statement announcing Kennedy’s intention to run for president dated January 2, 1960, estimated at $200,000.

In a statement, Paloger says that the president’s death in 1963 had a profound affect on him and fueled his interest in collecting artifacts from his life. The sale includes a cloth banner from Kennedy’s trip to Dallas that was displayed as part of the motorcade procession before his assassination, as well as a commemorative jigsaw puzzle showing Jackie receiving a bouquet of red roses in her iconic pink suit with matching pillbox hat. Two rare original photographs show the aftermath of the shooting, as Lyndon B Johnson is sworn in aboard Air Force One, with Jackie standing in her then-ruined suit next to him.

Bidding begins on January 17 and runs through January 23. See highlights from the auction below.

Images courtesy of RR Auctions.

Original photographs of LBJ being sworn in as President, by White House photographer Cecil Stoughton signed and dated 11/22/63. Courtesy RR Auctions.

Original watercolor painting by John F. Kennedy, 1960. Courtesy of RR Auction.

JFK painting, courtesy of Ronnie Paloger & RR Auction.

Original watercolor painting by John F. Kennedy, 1960. Courtesy of RR Auction.

John F. Kennedy’s handwritten draft announcing his intention to run for the presidency, January 2, 1960. Courtesy of RR Auction.

Original photographs from JFK’s Personal Diary/Scrapbook. Courtesy of RR Auction.