WHEN REPUBLICAN Stephanie Fattman was elected the Worcester County register of probate in 2014, John Dolan III was one of the employees she inherited.

Dolan had been working at the office for nearly 20 years years and didn’t want to leave, so he says he took a number of steps to ingratiate himself with Fattman. He says he switched his registration from Democrat to Republican in 2014, helped raise money for her campaign account, and he and his wife personally donated $4,000 to her campaign between 2015 and 2018. Dolan and his wife also donated another $1,850 to the campaign of Fattman’s husband, Ryan, a state senator.

“I said I would help her, so I helped her,” said Dolan.

But now Dolan is running as a Democrat against his former boss, and says all that earlier help should be viewed in a different context. “I did what I did to keep my job,” he said.

Campaigns for register of probate rarely attract much attention. The register oversees the processing of court paperwork related to such issues as estates, divorces, adoptions, and child custody cases. In most states, the register of probate is an administrative position, but in Massachusetts registers are elected to six-year terms in each county. The Worcester County office employs 35 people and the register earns $155,084 a year.

Fattman and Dolan offer voters two very different choices. Dolan, who will soon turn 66, is a 25-year veteran of the office who wants a chance to run it. He has no political experience and has raised far less money than Fattman, but he insists he has the background and experience needed to improve the office’s operation. Fattman is half of what qualifies, in the thin ranks of Massachusetts Republicans, as a rising GOP power couple.  She and her husband both defeated Democratic incumbents in the same year; she was 26 at the time, studying for her law degree at Suffolk University.

Fattman said when she came into office some employees worked second jobs and often came in to work at irregular hours, which she put a stop to. “There was a lot of mismanagement,” she said. She noted that Dolan worked closely with the previous register (“Dolan was part of that regime,” she said) but she did not accuse him of coming in late or engaging in mismanagement.

In her first term, Fattman said her office cut the turnaround on paperwork processing from three weeks to less than 24 hours, helped return $5 million abandoned in escrow accounts to rightful owners, and created an adoption program.

Fattman disputes any suggestion that employees were required or even urged to donate to her campaign to hang on to their jobs. “I’ve really kept politics separate from the office,” she said.

But it’s also clear that she is the politician in the race. Her campaign spent a whopping $134,741 between March 1 and August 31 and still had a balance in the account of $60,272. By contrast, Dolan spent $21,069 over that time period and had a balance of $19,410.

Dolan, who is still getting back on his feet after a lengthy hospitalization and rehab, is doing a lot less campaigning and relying more on a network of contacts he has built up over his years working in the probate office. He said he will not ask employees for political donations and focus all his efforts on improving the office. He said Fattman periodically sent donation requests to his wife and dropped subtle hints for campaign cash at the office.

He said employees aren’t being trained properly and service is poor, particularly for non-lawyers who need to do business with the office. “I just don’t agree with what they’re doing and I can do it better,” he said.

Dolan’s campaign has been a bit of an odyssey. The idea began taking shape in 2018, when he switched his political registration back to Democrat. A year ago, he said, a group of lawyers who regularly use the register of probate office began looking for someone to run against Fattman. At the time, Dolan was interested in running but not prepared to launch a campaign. Katia Wennerberg, a probate lawyer who had been a friend of Dolan’s for 13 years, decided to run, and says she was encouraged to do so by Dolan.

In late February, Dolan filed papers to set up his own campaign committee. He retired from his position at the register’s office in April.  The launch of his campaign didn’t sit well with Wennerberg (“I was dumbfounded,” she said) but she didn’t pull out of the race. Even though Dolan was still in rehab on primary election day, he ended up winning by a margin of 53-46, receiving 61,140 votes.

Miffed as she is, Wennerberg said she is supporting Dolan in the general election because she thinks Fattman needs to go. “She doesn’t show up for work, which is a problem. Even if she did, she doesn’t have the credentials to run the office,” she said.

Dolan’s absence from the campaign trail as he rehabbed prompted a lot of whispering that he was throwing in the towel. But Dolan said he’s going to see the race through.

“Some people said I’m dead. Some people said I can’t talk,” Dolan said in a phone interview. “I assure you I’m alive and well. I can walk and talk.”