WASHINGTON — John L. Sinatra Jr. checks all the right boxes for a federal judgeship. He excelled in school and in a legal career that carried him from Cleveland to Washington and back home to Buffalo, where his work wins praise from every side of the political spectrum.
But Sinatra's brother Nick, a Buffalo developer, is tightly tied to the right side of the political spectrum — and to Rep. Chris Collins, the Republican congressman who is pushing John Sinatra for the federal bench.
Collins invested between $3.5 million and $13 million in Nick Sinatra's real estate ventures since 2014, federal records show. Collins also loaned Nick Sinatra's company at least $1 million two years ago. Those business dealings produced between $65,000 and $350,000 in income for the congressman last year.
Then this year, Collins floated John Sinatra's name for a vacant federal judgeship in Buffalo, and the Trump administration did the same.
Good-government types said they're stunned that Collins is pushing his business partner's brother for a lifetime judicial appointment. Sinatra's candidacy also raises concerns among women lawyers because he would take the seat that the Obama administration wanted to fill with Buffalo's first-ever female district court judge.
Nick Sinatra refused to comment, deferring all questions to Collins' office, and John Sinatra did not return a request for comment.
Several Buffalo lawyers — including Daniel C. Oliverio, chairman of Hodgson Russ, the law firm where Sinatra serves as a partner — praised Sinatra.
"He certainly would have been on the radar screen for a federal judgeship without Nick Sinatra, Chris Collins or anybody else," said Oliverio, a political independent.
But Robert Galbraith, senior research analyst for a Buffalo-based good-government group called the Public Accountability Initiative, said John Sinatra's nomination would raise an important question.
"Is it his legal proficiency or his brother's relationships with Chris Collins and Donald Trump that qualifies him for the position?" Galbraith asked.
A web of connections
Collins put money down in a half-dozen Sinatra & Co. real estate deals since 2014, including apartment complexes in Cheektowaga and West Seneca and the Woodlands Corporate Center in Wheatfield.
They also invested together on apartment complexes in San Diego and suburban Chicago. Collins' spokeswoman, Sarah Minkel, said he loaned Sinatra & Co. more than $1 million to finance that deal in San Diego.
"Chris is a passive investor," Minkel said. "He invests in ideas. Sinatra & Co. comes up with ideas, brings them to fruition and manages them. Very little of Chris' time is involved, and he gets the same treatment and conditions as every one of Sinatra & Co. investors."
Collins got to know Nick Sinatra years ago, when Sinatra worked in the administration of President George W. Bush, Minkel said.
A graduate of Yale University and the Wharton School of Business, Nick Sinatra — a Kenmore native — returned to Buffalo in 2009 to start his real estate company. Sinatra & Co. now has assets of nearly $350 million, according to the company website.
Sinatra became politically active in Buffalo, too. Federal records show he has donated $56,714 to Republican candidates and committees in recent years , including $10,611 to Collins. Collins and Sinatra have also hosted GOP fundraisers.
Meantime, Collins co-sponsored a bill that could have boosted Sinatra's company.
Sinatra used the Historic Preservation Tax Credit to help finance several of his projects. And earlier this year, Collins co-sponsored a bill that would have boosted that tax credit from 20 percent to 30 percent.
That tax credit was not used on the projects on which Sinatra and Collins teamed up, Minkel noted. And now that tax credit is in danger, given that the House tax reform bill — which Collins supports — would eliminate it.
Still, Collins' support for a higher historic tax credit raises ethics concerns, said Craig Holman, public affairs lobbyist for Public Citizen, a good government group.
He noted that last year, Collins helped write a bill that could have benefited Innate Immunotherapeutics, an Australian biotech company in which Collins is the largest investor.
Collins' habit of talking up Innate's stock remains the subject of a House Ethics Committee investigation. And now Holman sees Collins again backing legislation that could boost one of his business interests.
"It reflects what we've seen from both Chris Collins and Donald Trump: the mixing of personal business with public responsibility," Holman said.
A new federal judge?
Collins was the first House member to back Trump for president, and he appeared on news shows dozens of times to boost the GOP candidate.
So when Trump won, Collins — a businessman-turned-politician like the new president — won an unusual amount of influence. Trump called on him for help in filling political positions, including the open slots for U.S. attorney and a federal judge in Buffalo.
"I expect these nominations to start off on a new page with our new Congress and newly elected president," Collins said after Trump's election.
Collins quickly started talking up John Sinatra Jr. as a possible nominee for the judgeship.
"John Sinatra Jr. is a good attorney with a great legal mind," said Minkel, Collins' spokeswoman. "His resume and background speak for itself, and he has strong support in the community."
In July, the Trump administration sent a list of likely judicial appointments to New York's two U.S. senators, who are both Democrats and who would have the power to block any nominee they didn't like.
Sinatra's name was on that list, sources said, but Sinatra's nomination has not moved any further than that. Both Senate Minority Leader Charles E. Schumer and Sen. Kirsten E. Gillibrand declined to comment for this story, and Tyler Ross, a White House spokesman who used to work for Collins, did not respond to a request for comment.
Sinatra's prospective appointment raised concerns in Buffalo, though.
Galbraith already had traced the connections between Collins and Nick Sinatra on the Public Accountability Initiative website, littlesis.org. Told that Collins was pushing Sinatra's brother for a federal judgeship. Galbraith likened it to Collins' efforts, documented in an Office of Congressional Ethics investigation, to hawk Innate's stock to Buffalo business and civic leaders.
"We again have something that looks like Collins leveraging his official position to reward people in his personal network," Galbraith said.
In addition, some local lawyers groused that Collins had pushed Sinatra to replace Schumer's choice to fill the position: Buffalo lawyer Kathleen M. Sweet, who would have been the first female U.S. district court judge ever to serve in Buffalo.
"I think there is a segment of the legal community that would like to see diverse nominees," said Melinda G. Disare, president of the Bar Association of Erie County.
Then-President Barack Obama nominated Sweet to fill the slot of U.S. District Court Judge William M. Skretny in March 2016. But the Senate's GOP leadership sat on late-arriving Obama appointments, hoping Trump would win so they could fill those seats with Republicans.
Some women lawyers in Buffalo were disappointed, though, to see Trump pushing yet another white male for a federal judgeship.
"It's really important that the bench reflect the people it serves," said Anne E. Joynt, president of the Western New York chapter of the Bar Association of Western New York. "The more diverse, the better."
A qualified choice
Buffalo lawyers from both political parties said John Sinatra is qualified to be a federal judge.
"He's a skilled practitioner, a very thoughtful guy, and he's got a great judicial temperament," said Dennis C. Vacco, a former U.S. attorney in Buffalo, a former state attorney general and a Republican.
Terrence M. Connors, a prominent Democratic attorney, said Sinatra works on complicated estate settlements, business deals gone bad, and the like.
"He's low-key, hard working, smart, solid and trustworthy," Connors said. "John Sinatra has established a reputation as one of the top commercial litigators in our region."
Sinatra got his undergraduate and his law degree from the University at Buffalo, where he served on the law review. He clerked at the state's highest court and began his career at the Cleveland office of Jones Day, one of the nation's top law firms.
He later worked as a Department of Commerce lawyer under President George W. Bush, a Republican. Then Sinatra came home to Buffalo to join Hodgson Russ.
That law firm's chairman, Oliverio, said that with nearly 20 years of experience in the federal courts, Sinatra is prepared to be a judge.
"Regardless of John being a white male, you would hope people would focus on his qualifications and readiness to serve on the bench," Oliverio said.
Sinatra joined the conservative Federalist Society — as do many GOP judicial hopefuls — back in law school, Oliverio noted.
To demean Sinatra because of his brother's connections to Collins is "below the belt, incorrect and unseemly," Oliverio added.
"He's extremely qualified in terms of his trustworthiness and experience," Oliverio said.
Critics of Sinatra's pending appointment said they're not attacking him personally. They said it's appropriate, though, to question why Collins wants his business partner's brother to serve on the federal bench.
"This looks like self-dealing," said Holman, of Public Citizen. "It's another thing Chris Collins has done that would leave people asking: 'What are you doing?'"