You’re sailing along after announcing your candidacy for president — the third in your family. You’ve steadied yourself after a series of wobbly answers on the wisdom of your family’s second Iraq war. You announce you’ve snagged one of the big gets among Republican fundraising poobahs — a football team owner, no less.

Jeb Bush had been looking like he held a first-class ticket (of course) on the express train to the sunny Republican presidential uplands. Then along came Chief Justice John Roberts to spoil it all. When the roll is called on the winners and losers in the Obamacare decision from the U.S. Supreme Court, the biggest loser is John Ellis Bush. Engrave it in stone.

Engaged Republicans, the sorts who attend political events and vote in caucuses and primaries, will run the gamut from baffled to infuriated at Roberts’ decision to rule against the plain English language of the law that passed with no Republican support in Congress. They will wonder how Roberts, said to be a reliable conservative, could again contort himself into the justice from Cirque du Soleil, Washington company, to advance the cause of left-wing collectivism.

There may be many theories and explanations for Roberts’ opinion, though Justice Antonin Scalia’s description of it as “absurd” ought to suffice. Reasonable people can disagree on the fine points in a free and civil society. A broad consensus could quickly develop on one lethal conclusion: Bushes cannot be trusted to select members of the Supreme Court of the United States. It is too risky to give Jeb Bush the chance to appoint the next Roberts or David Souter.

Remember David Souter? He was the modest-in-all-things justice on the New Hampshire Supreme Court that President George H.W. Bush plucked out of obscurity to fill a vacancy on the nation’s highest court. Bush White House chief of staff John Sununu came up with the idea. He had appointed Souter to the New Hampshire high court when he was governor. What could go wrong? Sununu was a conservative, so Souter must be too.

Souter was not. Once confirmed, Souter executed a ferocious left turn and stomped on the accelerator. Sununu, who is not given to public displays of introspection and regret, has been mewling that in the vetting process Souter deceived him and the first President Bush. Maybe they just didn’t ask many questions. Sununu vouched for Souter’s bona fides, helping him sail to a 90-9 win in the Senate, with only Democrats voting against him. Souter’s perch in the liberal wing of the court, an advocate of greater judicial power, won him the title George H. W. Bush’s worse mistake — in a fierce competition.

And now George W. Bush’s gift of John Roberts strikes again. The Washington establishment denizen enters the stiff competition to become the second Bush’s worst mistake in the judgment of conservative loyalists.

Souter and Roberts may prove two burdens too many for Jeb Bush. Why take the chance? Republicans will ask themselves. These Bushes, who may be good at many things, cannot be trusted to pick sound members of the Supreme Court. When there are so many other promising choices seeking the Republican nomination for president, party members may decide that Roberts has reminded them that the price of another Bush is too high, the consequences too risky.

Jeb Bush may be able to explain away a lot of history, but the Souter/Roberts inheritance could prove a legacy too heavy. With so many other good choices in the field, Republicans may not want to risk being duped like a Bush — or by one — again.

Kevin Rennie is a lawyer and former Connecticut state legislator. He has been a columnist with the Hartford Courant for over a decade. He wrote this piece for InsideSources.com.