The Red Sox have decisions to make with two roster-related deadlines looming on Tuesday and Friday.

They have until 4 p.m. ET Tuesday to add eligible prospects to their 40-man roster to protect them from next month’s Rule 5 Draft, and until 8 p.m. ET Friday to non-tender any of their arbitration-eligible players.

There’s a strong possibility the Red Sox opt to solve two problems at once. They have dozens of Rule 5 eligible players this year but realistically will only clear roster space for a select few, such as hard-throwing righty David Sandlin, who posted a 3.97 ERA over 14 starts between Double-A and Triple-A, with 71 strikeouts over 70.1 innings. He was in consideration for a late-season call-up before he struggled with a move to the bullpen.

The Red Sox could also opt to take toolsy outfielder Miguel Bleis off the table, but he’s tumbled down the prospect rankings since shoulder surgery in June ’23, produced inconsistently, and his highest-level experience is 30 games at Double-A Portland this year. Plate discipline continues to be an issue, too; Bleis walked 41 times in 107 games this season, only two more free passes than he drew in 95 games the year before. MLB.com listed Bleis as Boston’s toughest Rule 5 decision.

Teams will make trades before Tuesday’s deadline, but the easiest way for the Red Sox to create space is to non-tender. Right-handers Tanner Houck and Kutter Crawford are likely safe, as are infielders Triston Casas and Romy Gonzalez, lefty Brennan Bernardino, and catcher Connor Wong.

The two most likely non-tender candidates are right-hander Josh Winckowski, who missed most of the season with a right flexor strain and has struggled to find consistency when healthy over the last few seasons, and veteran first baseman Nathaniel Lowe, who is projected to earn $13.5 million in arbitration. If the Red Sox wanted to free up more than two spots for Rule 5 protection, lefty Jovani Morán or infielder Vaughn Grissom could be on the proverbial chopping block.

The organization’s newfound success at developing homegrown pitching will likely prove something of a double-edged sword at this year’s draft. Righty Tyler Uberstine excelled in Double- and Triple-A this year and will almost certainly be scooped up. Fellow righty Yordanny Monegro underwent Tommy John surgery this summer, but is still talented enough that teams may be willing to bite.

Left-hander Shane Drohan could find himself Rule 5’ed again this year. The Red Sox did not protect him in ‘23, but the White Sox returned him the following June, after nerve decompression surgery. Drohan has bounced back well since rejoining his original organization and impressed in Triple-A Worcester this year, where he posted a 2.27 ERA over 12 starts, struck out 67 batters in just 47.2 innings, and held opponents to a .185 average.

There’s also the possibility the Red Sox make a selection. Right-handed relievers Garrett Whitlock and Justin Slaten are two of the biggest Rule 5 success stories in recent history.

Though known as the Rule 5 draft since 1941, the system originated in 1892. Nearly a decade before the founding of the American League in 1901, and the first World Series in 1903 – which the Red Sox won as the Boston Americans, by the way – the “Selection of Players” allowed MLB teams to draft at will between October and February.

Today’s iteration of the Rule 5 takes place in a single day, and comes with more strings attached. The poaching team must pay their pick’s former club $100,000, but the more significant cost is the stipulation that they must keep the player on their 26-man big-league roster for that entire first year. Said player must also be active for a minimum of 90 days; if placement on the injured list prevents them from reaching 90 days, they must fulfill the remainder of the requirement the following season.

A Rule 5 pick can only be removed from the active roster via outright waivers. If the player clears waivers, their team must offer him back to his former team for $50,000. If they decline to reclaim him, his new team can outright him to the minors.