Throughout his tenure in the Senate, Sen. Joe Manchin (D-WV) often served as a thorn in the Democrats’ side by cementing himself as a centrist roadblock to many of their agenda items.

Because of the Democrats’ slim majority in the Senate, Manchin was often the make-or-break vote for party-line votes, forcing the majority party to negotiate deals with the West Virginia senator to get him on board. This frequently led to liberals compromising some of their top priorities and sinking crucial proposals of President Joe Biden’s agenda.

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To be sure, Manchin appeared to enjoy the role he played in the upper chamber. The West Virginia Democrat often butted heads with Biden, becoming more critical of the president’s policies over the last several months on a series of matters.

Manchin announced on Thursday he would not seek reelection to the Senate, sparking speculation about what he may pursue amid rumors of a third-party presidential bid. Doing so would pit Biden and Manchin against each other in a different way than they’ve previously dealt with, setting the stage for another rivalry the president must face as he seeks reelection.

Here’s a roundup of the times Manchin clashed with Biden ahead of his retirement announcement that could play a role in the 2024 cycle:

Manchin’s support for Biden’s agenda plummeted over last 11 months

During Biden’s first two years in the White House, Manchin supported the president’s policies and voted in line with his position a majority of the time, according to data compiled by FiveThirtyEight. However, that support saw a significant drop after the 2022 midterm elections, as Manchin entered the last stretch of his Senate term.

Throughout the 117th Congress, which lasted from January 2021 to January 2023, Manchin voted in line with Biden’s position 87.9% of the time. However, over the last 11 months, that number has plummeted to just 21.4% — a 67-point drop.

Those numbers were initially attributed to the fact Manchin would face a tough reelection fight in a state where former President Donald Trump won by 39 percentage points in 2020. But now, with Manchin retiring, it raises eyebrows as to why the West Virginia Democrat was so keen on distancing himself from the president.

Manchin sank key Biden ‘Build Back Better’ legislation

Manchin also played a key role in sinking one of Biden’s key legislative priorities, the Build Back Better Plan, which sought to invest in creating high-quality employment by investing in a handful of social, infrastructural, and environmental programs.

Manchin and fellow centrist Sen. Kyrsten Sinema (I-AZ) played a key role in negotiating the legislation, as the two positioned themselves as holdout votes due to several provisions in the bill. The pair of senators helped scale back the size and scope of the legislation, particularly how much the bill would cost the government if implemented.

Despite those efforts, Manchin came out as a hard "no" on the bill — sinking the legislation altogether as he would have been the key swing vote to push the legislation past the finish line.

“I just can't. I've tried everything humanly possible. I just can't get there," Manchin told Fox News in December 2021. “I've tried everything I know how to do, and the president has worked diligently. He's been wonderful to work with."

Manchin becomes first Democrat to oppose Biden judicial nominee

Manchin turned heads in mid-May when he voted against Nancy Abudu’s confirmation to sit on the U.S. Court of Appeals for the 11th Circuit, making him the first Democrat to oppose one of Biden’s judicial nominations.

A spokesperson for Manchin said the senator voted against her confirmation to avoid elevating “partisan advocates” to partisan courts, especially at a time when voters have lost faith in the country’s judicial system. Abudu was still confirmed to the position despite Manchin’s opposition due to the absence of three GOP senators.

Manchin threatened to derail signature Biden law that he helped craft

One of Biden’s top legislative victories throughout his term was the passage of his Inflation Reduction Act, an all-encompassing landmark bill seeking to reduce the nation’s deficit while addressing climate, prescription drug prices, and domestic energy production.

The law was a heavy lift in the Senate, in which Manchin played a major role in pushing the legislation past the finish line. As part of that deal, the West Virginia Democrat struck a deal to give the legislation its name, which Biden later said he regretted.

Manchin later reversed on that deal, expressing frustration with the Biden administration’s execution of the law, lamenting the president was using it to advance his “radical climate agenda.” Manchin later went on the offensive to say he would vote to repeal the act if it came up for a vote in the Senate.

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"Since President Biden signed the Inflation Reduction Act into law, Washington hypocrisy has been on display, with both sides politicizing the bill to gain a partisan advantage," Manchin wrote in a September op-ed. "On the far left, the administration has touted the bill as a transformational piece of green-energy legislation."

Manchin even decided to skip a major White House event celebrating the one-year celebration of the act’s passage in August in another sign the West Virginia Democrat sought to distance himself from the legislation.