The Winter Meetings are here, and that means the offseason is about to move forward in earnest. It also means that we need to prepare for the Rule 5 Draft that takes place on the last day of the conference every year. The last prominent player the Yankees lost in the draft was Tommy Kahnle to the Rockies in 2014, and he’s managed to find success so far. In 2016, there are a few more names that could end up on other teams by the end of the week.

Jake Cave | OF

This will be the second year in a row Cave won’t be protected from the Rule 5 Draft. He was taken by the Reds last offseason but somehow failed to make their Opening Day roster, despite the state of that team. An ability to hit for average and make contact got him some early prospect attention, however, that has mostly been washed away by his lack of standout power and speed. The Yankees might have normally added Cave to the 40-man roster by now if it wasn’t for the fact that they seem to have an endless supply of outfielders with more upside than him.

All this being said, Cave is the kind of player who gets taken in the Rule 5 Draft. He has substantial experience in Triple-A at this point, can play all three outfield positions, and can do a little bit of everything. It’s important to keep in mind that, as a two-time draftee, he would be eligible for free agency if he is taken but doesn’t stay on his new team all season. It’s very possible that this could be the end of his career with the Yankees.

Cale Coshow | RHP

Before the 2016 season, Coshow looked like an easy candidate for the 40-man roster at this point. He pitched well between the bullpen and rotation across three levels in 2015. Coshow looked like a future big league reliever, and he even managed to sneak into the team’s top 20 prospects. He struggled far more than usual this year, to the point where his 5.0 BB/9 prevented him from ascending beyond Double-A Trenton.

Being held off the roster just goes to show you how one bad year can make all the difference. Now there’s a chance that he could be taken, but with his lack of experience, it’s difficult to tell if he stands a chance at a major league job somewhere else.

Caleb Frare | LHP

Frare has spent much of his professional career on the disabled list. He finally found some success in 2015 and continued on that track to a 0.92 ERA in 2016, despite never finding his way out of High-A Tampa. The 22-year-old Frare isn’t exactly a can’t-miss prospect, but he held lefties to a .458 OPS this past year. A team who could use an inexpensive lefty specialist could look to him as an alternative addition. It’s unlikely to turn out well for him, but that doesn’t mean it won’t happen.

Brady Lail | RHP

After a few years of unlikely prospect success, Lail’s status as a former 18th-round pick finally caught up with him somewhere between Trenton and Scranton last year. His strikeout numbers vanished back in 2014, however, he continued to find success despite the drop. With no ability to miss bats, he seemingly pitches to contact, which has not done too much for him in Triple-A. It’s more than likely that Lail has hit a wall, but given the state of pitching around the league, and the innings total he has accumulated, it’s not impossible that someone would take a chance on him for a time.

Caleb Smith | LHP

Another unlikely success story, Smith defied expectations and pitched well as a starter between 2014 and 2015. He reached Trenton after two years in the rotation before returning to the bullpen in 2016. Despite improved peripherals, he didn’t blossom like the organization had hoped and he spend the year in Trenton. At this point, he’s a 24-year-old lefty reliever who isn’t particularly effective against left-handed hitters. Still, there’s a chance he gets picked up by a team hoping to find a useful swingman.

Tyler Webb | LHP

Once considered to be a closer in the making, Webb has proven that he can strike hitter outs, but he isn’t the shutdown reliever they were hoping for. The Yankees actually tried him in the rotation for a time this season as they hoped to turn him into something other than a LOOGY. At the age of 26, the Yankees have likely come to terms with who he is and are prepared to move on.

Given his potential role and how teams generally treat this draft, Webb probably has the best chance of being taken out of anyone else on this list. Left-handed relievers always seem to get a million chances, so there’s a real chance Webb would stick with any team that wanted him.

Other Yankees prospects who are eligible for the Rule 5 Draft but are far less likely to be taken include outfielder Rashad Crawford, catcher Luis Torrens, and shortstop Abiatal Avelino.