Even some of Mayor John DeStefano Jr.’s closest allies are calling his request for a $25,000 pay raise a political mistake.

“It’s come as a surprise to the aldermen I’ve talked with … especially the aggressive number,” Ward 9 Alderman Roland Lemar, a self-proclaimed “DeStefano loyalist” said.

The proposed raise, which came Thursday on the heels of DeStefano’s re-election to his eighth term as mayor, would increase his salary from $115,000 to $140,000.

Most of the half-dozen aldermen interviewed said the decision to ask for such a large raise sets the wrong tone in the election’s aftermath and the mayor may ultimately have to compromise for a smaller amount. Lemar called DeStefano’s request “inappropriate.”

While aldermen said a system that requires the mayor to submit his own salary proposal is flawed, they disagree on whether the purpose of a raise should be merely a cost-of-living adjustment or whether it should be a reward for good leadership. Although the board must amend city ordinance in order for the proposal to take effect, they can modify the size of the final increase.

Lemar said the announcement that the mayor is seeking a raise was not expected by members of the board.

“It’s never been a part of any conversation I’ve had with the mayor or his staff in the months before the election,” he said.

Lemar said that while he personally thinks the mayor deserves the increase, he predicts the mayor will ultimately receive a raise of $5,000 to $10,000.

When negotiated ahead of time, such as part of a collective bargaining agreement, he said that pay raises make sense but that they should not be instituted retroactively as “a reward for a good job in the past.”

The eventual decision may rest in large part on what the aldermen perceive to be their constituents’ beliefs. Ward 3 Alderwoman Jacqueline James and Ward 28 Alderman Mordechai Sandman both said residents — whose taxes have increased in the past year — will want to hear good reasons for the raise. Both said they are currently undecided on whether they will support the proposal and if so, to what degree.

“It’s a lot — it’s really a lot,” James said. “$25,000 is a lot at one time. How are we going to justify it to the taxpayers?”

She said the timing of the request directly following the election could make voters feel they had been caught off guard.

Still, James said she does not think the mayor would have proposed the pay raise unless he already thought he had enough votes lined up in support.

But Lemar said he thinks the mayor might have requested such a large increase with the expectation that the board would reach a consensus on a lower figure.

City Hall Spokeswoman Jessica Mayorga said the timing of the request does not bear on its legitimacy. She said the mayor’s exceptional dedication to New Haven over the past 14 years and his lack of a raise in the preceding four years make him well-deserving of the pay increase.

“He’s the chief executive officer night and day,” she said. “When you break it down, it’s really not a radical increase.”

Many aldermen interviewed said it is not relevant that the mayor has not received a pay increase in four years because he has previously chosen to forgo seeking raises because of city budget issues.

In 2005, he requested, but later withdrew, a proposal while running for governor. Mayorga said he retracted the request for city fiscal reasons.

Board of Aldermen President Carl Goldfield said he thinks there is a consensus among his constituents that the city is in much better shape today than it has been in a long time because of DeStefano’s leadership.

He said that the aldermen would consider many factors when making the decision but that process is not as simple as in the private sector, where there are established benchmarks by which to judge.

But Goldfield said there is a wide range of views on the board.

“I think this will be a healthy discussion,” Goldfield said. “Despite [the board] being accused of being a rubber stamp [for the mayor], if we give him a full raise, it will be because we think it’s the right think to do.”

Under the current system, aldermen said, the mayor finds himself in a difficult position. The city charter requires that the mayor submit the pay raise request by the beginning of the upcoming calendar year.

“I think it’s awkward that the mayor has to propose his own salary increase,” Ward 5 Alderman Jorge Perez said. “Asking for a raise before [the election] would look cocky, and after is — after. We should come up with a standard [salary] system.”

He said mayors should be paid on a predetermined scale based on tenure. As is the case with most all government jobs, he said, performance should not be a factor.

But whatever problems exist with the system in place, aldermen said that before they would be willing to give the mayor a pay raise, they would want to evaluate the justifications provided for the raise.

Aldermen said they would consider what other mayors of similarly sized cities in Connecticut and around the country make, as well as pay scales for jobs in the private sector with similar skill sets and municipal management union salaries.

Still, many also said the only truly objective way of measuring the mayor’s performance is his electoral success in the last election, in which he won with 72 percent of the vote.

But Green Party candidate Ralph Ferrucci, who lost to the mayor in the last week’s race, said the percentage of votes should not be paraded around as indicative of the mayor’s success considering the voter turnout was less than 20 percent.

He said he will argue at the Finance Committee meeting — which will be open to the public — that DeStefano deserves a cost-of-living adjustment, minus a penalty for what he called his poor performance.

Another alderman who asked to remain anonymous said the real fiscal impact is not just the $25,000, but the substantial increase in the mayor’s pension that would result from the raise.

Municipal pensions are calculated as 75 percent of the average of a city employee’s salary over their final three years of employment, the alderman said.

If the raise were passed, upon DeStefano’s retirement, the city would owe at least an additional $350,000 to the mayor over the next 30 years, as compared to a pension calculated based on his current salary, the alderman said.

Political Science professor Douglas Rae, who served as the chief administrator officer under former Mayor John Daniels, said that although he is not a big supporter of DeStefano, he cannot find fault in the mayor’s request for a pay increase.

Rae recounted a meeting he had with top staff at the National League of Cities, just after DeStefano had finished his term as league president, at which he asked staff members for their honest opinions of DeStefano.

Rae said they responded that DeStefano was the “hardest working” and “quickest study” of any president for which they had worked.

“I don’t think $140,000 would be hard to justify,” Rae said. “[But] taxpayers who make $30,000 and pay $6,000 in taxes are not going to be pleased.”

The mayor’s proposal will be on the agenda of the Nov. 20 meeting of the Finance Committee.