Biden and Bloomberg are now making a similar appeal to voters based on their records and their perceived strengths against Donald Trump. But while Biden has to survive the early state gauntlet, Bloomberg is skipping the first four contests while spending hundreds of millions of dollars on ads and a massive nationwide organization.

Sheekey’s donation seems to underscore a point often made by Biden’s aides and allies and echoed in their approach to his chief rivals: Nearly everyone, they contend, was happy to heap praise on Biden until their own political ambitions got in the way. When Biden clashed with Kamala Harris in the first debate, allies pointed to her glowing assessments of him when she ran for Senate.

During heated exchanges with Pete Buttigieg last weekend in New Hampshire, Biden’s rapid-response director tweeted out a video of Buttigieg subbing for Biden at a county chairs event in August 2018.

“It makes you reflect on exactly how a 36-year-old small-city Midwestern mayor...finds himself before the biggest gathering of Democrats in the state of Illinois,” Buttigieg said in the clip. “A great opportunity. Trying to fill the shoes of an American giant like Joe Biden.”

Sheekey, a longtime adviser and one of the first to counsel Bloomberg on his unlikely run for New York City mayor, has a long relationship with Biden. He was singled out to replace Biden's vice presidential chief of staff Ron Klain, a move that was scuttled by top Obama officials who feared his first loyalty would be to Bloomberg.

“Kevin has deep respect for the vice president and almost went to work for him on several occasions,” Bloomberg spokesman Stu Loeser told POLITICO. “This contribution, obviously, is from before Mike decided to run for president.”

Sheekey and Bloomberg’s advisers have walked up to the line with Biden. Central to Bloomberg’s decision to enter the race was his belief that none of the Democrats—Biden included—have what it takes to beat Trump.

Biden’s campaign declined to comment on the donation.