Another core member of the Boston Red Sox is packing his bags to bolt in free agency, as right-handed pitcher Nathan Eovaldi has agreed to a two-year deal with the Texas Rangers.

It stings to see another popular player leave town. It’s frustrating that the two-year, $34 million offer from the Rangers is one that Boston could have comfortably matched, and yet there’s little indication that they made an honest effort to retain the former All-Star. The Red Sox did make a multi-year offer earlier this offseason but recent reports indicated that they had fallen behind in the race for Eovaldi. It’s flat out baffling that they let him walk without putting up much of a fight when you realize how the Red Sox approached last season’s trade deadline.

Boston still held a Wild Card spot in mid-July but there were already clear signs that the team was beginning to crumble. Sitting 3.5 games out of a playoff spot as we reached the trade deadline at the end of the month, Boston took an odd approach by straddling the line between buyer and seller. Christian Vázquez and Jake Diekman were shipped out while Tommy Pham, Reese McGuire and Eric Hosmer were brought in. They sold pieces that weren’t in their future plans while simultaneously buying veterans to address weaknesses for a playoff push down the stretch.

We know how that turned out. The results were mixed from the new additions but they weren’t nearly enough to make a difference in the competitive Wild Card chase. The departure of Vázquez wasn’t well received in the clubhouse, testing the chemistry of a team that was already plummeting as injuries piled up. The Red Sox finished last in the AL East and they weren’t even within shouting distance of the playoffs as they limped to the finish line.

Their perplexing path to the trade deadline has led to a nightmare scenario for the Red Sox. They were a last place team out of playoff contention that still paid the luxury tax.

Red Sox losing Nathan Eovaldi is even worse when realizing trade deadline failures

The Red Sox were still fooling themselves into believing that they could re-sign Xander Bogaerts. Then the free agent market exploded and they weren’t willing to leave their comfort zone to sign the star shortstop to the type of long-term deal the evolving market demanded. Nobody was predicting the bidding war for Bogaerts would reach that level back in July, so it’s understandable that trading him was never on their radar.

The same cannot be said for Eovaldi, though. While he dealt with another injury-plagued season, his dominant finish (2-0 with a 2.25 ERA over his final five appearances) proved he still had plenty to offer to a contender. Factor in his postseason track record, and Eovaldi undoubtedly could have fetched something of value at the deadline.

It’s mind-boggling that the Red Sox held on to Eovaldi at the deadline only to bow out of the race when it came time to re-sign him. They could have shed his remaining salary in order to dip under the competitive balance tax threshold. Now they are suffering the consequences of their inaction on multiple fronts.

Bogaerts and Eovaldi both declined qualifying offers from the Red Sox, which means the team will get compensatory picks in the 2023 MLB Draft now that the two players have signed with other teams. Those picks would typically come after Competitive Balance Round B, likely in the 70s. But since the Red Sox were over the tax threshold last season, part of the penalty entails those compensatory picks being pushed back after the fourth round, which now projects to be picks Nos. 133 and 134, according to Ian Cundall of Sox Prospects. They also miss out on about $1 million in bonus pool money for next year’s draft based on this year’s slot values.

The reduced draft pick compensation would be irrelevant if the Red Sox had been able to re-sign their stars. Unfortunately, they never came close.

Chaim Bloom acted as if he had been blindsided by the massive contract that Bogaerts received from the Padres despite that several other teams submitted more appealing offers than the Red Sox did. Either he misread the market to a negligent extent or ownership is stubbornly holding firm to their philosophical aversion to long-term contracts.

Eovaldi required only a short-term commitment for essentially the same salary that they paid him on his last contract. After being surpassed by several suitors and never making an offer competitive enough to keep them in the mix as Eovaldi narrowed down his choices, we’re left to wonder if the Red Sox were ever serious about re-signing him, which makes it more absurd that they didn’t trade him when they had the chance.