What are the following?

1. Obamacare.

2. Rejecting debt packages.

3. His Middle East policy.

4. Refusing to extend the George W. Bush tax cuts, then extending them and then refusing to extend them again.

5. Elevating politicking over serious policy.

These items, in no particular order, are five avoidable, critical errors by President Obama, most aided and cheered by the left. Each damaged Obama and his party, resulting in political and/or policy debacles.

They should remind right and left that Obama’s current dilemmas need not have occurred and that a rotten political and economic environment might have been ameliorated.

It is now firmly accepted by a raft of polling two years after Obama took extraordinary steps after the election of Sen. Scott Brown (R-Mass.) to ram through his “historic” health-care bill on a strict party-line vote: It was not simply a policy mess, as we have learned from each revelation about its design flaw. It rallied the right, cost the Democrats the House, suggested that he valued this issue over the economy, helped paralyze job creators, launched a conservative litigation extravaganza and earned the disapproval of the public. If he loses at the Supreme Court, he looks like a fool for wasting most of his term, and if he wins, he has to defend very unpopular legislation.

What could he have done? He could have agreed to a short list of reforms agreeable to both sides and instead focused on jobs (not delay on the three free-trade agreements) and/or tax reform. The economy and his political situation (not to mention the House Democrats) might all have been in better shape.

As great an error (maybe worse) as Obamacare was his repeated refusal to embrace a debt/tax package on a bipartisan basis. First he assembled and then rejected the findings of the Simpson-Bowles debt commission. Then he invited and sabotaged the “grand bargain.” Had he done either, he would have made significant progress on our fiscal situation, boosted the markets avoided a credit downgrade, satisfied moderates and split the GOP.

In pursuing a bizarre Middle East policy — engaging Iran, remaining mute on the Green Revolution, antagonizing Israel, dragging his feet on sanctions, doing nothing effective on Syria and leaving no residual force in Iraq — he managed to embolden Iran, convey weakness to our allies, offend both the Palestinian Authority and the Israeli government, appear feckless to democracy reformers in the region, and offend a key Democratic constituency, Jewish voters.

Instead, he might have picked up on the gains made during the Bush administration regarding the Palestinian-Israeli conflict (including the exchange of letters between President George W. Bush and Israel Prime Minister Ariel Sharon regarding settlements). He could have rhetorically, economically and diplomatically aided the Green Revolution and, when it was crushed, moved swiftly to sanctions while keeping the military option credible. Rather than rap Israel on the knuckles for not signing onto the Non-Proliferation Treaty , he could have rallied regional players to prevent Iran’s acquisition of nuclear weapons. He could have promptly aided in Bashar al-Assad’s ouster.

In addition to nixing the Simpson-Bowles and grand bargain deal, he repeatedly got tangled up in the extension of the Bush tax cuts. He refused to extend them before the 2010 midterms. Then he did, after the election. Now, on the precipice of the fiscal cliff and despite advice of Bill Clinton, Larry Summers and others, he is once again refusing to take off the table a hug tax hike while the economy is weak. Had he pursued bipartisan tax reform (lower the rates, broaden the base), this could have been avoided.

And lastly, whether it was putting David Axelrod in the mix on the decision over a troop surge in Afghanistan or coming up with unserious budgets that bore the hallmark of political hacks like Valerie Jarrett rather than economists like Gene Sperling or veering left on his fall 2011 bus tour rather than toward the center to work with Congress, Obama again and again elevated partisanship over policy and cronies over more capable Democratic centrists. This, I suspect, was a perfect reflection of his own outlook. He was never a policy workhorse in the Senate. His politics is about using his (overvalued) political persona to acquire and retain power. Because he refused to question his own skill at the bully pulpit, his presidential stature suffered from extreme over-exposure and hyper-negativity. In refusing to understand the other side’s substantive arguments, he turned policy disputes into bitter partisan wars in which he regarded opponents as liars or intentionally out to harm the country.

It’s amusing to conservatives to see the same liberal crowd that goaded him in the wrong direction on these issues continue to spout advice. Be more adversarial! Spend more! The best advice his fan base in the media could give him would be: Ignore us — we’re clueless. Thankfully for the Republicans, the left punditocracy will never admit error, and neither will Obama.